road trip ideas near chicago

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19 Awesome Road Trips from Chicago (with Timings)

Keeping your introduction to road trips from Chicago short and simple, let’s take a look at the summer, winter and weekend favourites!

The city of Chicago is awesome and all, but it’s also a great starting point for some great Chicago road trips. The city’s prime location acts as a portal to the Midwest – from historical cities to sprawling state parks and urban-stress-relieving beer. 

Best Chicago Road Trips in Summer

If you’re looking for one of the longest Chicago road trips, how about driving from Chicago to New Orleans ? If you’re thinking a little shorter, then read on…

Distance: as far as you can go

No American road trip is complete without covering some part of classic Road 66 – of which, lucky for us, kicks off in Chicago!

Snap a selfie at the official sign between East Adams and South Michigan Avenue then check-off stops such as the Gemini Giant, the Pontiac murals, Lincoln Presidential Library and more. If you can spare a month, make it all the way down to the Pacific Ocean.

2. Illinois’ Great River Road

Distance: 3.5-hour drive

In a seemingly never-ending chain of historical sites and activities, the drive along Mississippi River to East Dubuque is one of the best road trips from Chicago.

Moline and Rock Island are two cool detours but you can head straight for East Dubuque for its Chicago Great Western Railway Depot Museum. John Deere Pavilion lets you hop from car to farm machines, while the city Nauvoo shows off many historic homes. 

3. Lake Michigan to South Haven

Distance: 2.5-hour drive

Escape the heat by packing your car with beach gear and setting off for a nice drive around Lake Michigan and towards South Haven.

There are plenty of berry farms along the way so you can stain your hands with blueberries; or maybe you prefer to climb up a lighthouse?

To take your road trip even further, bring a bike! Cruise along the water front; take a dip or two. 

Do you have a favourite road trip quote? Click for the best long drive quotes to inspir e your next adventure!

4. Shawnee National Forest

Distance: 6-hour drive

One of the longest Chicago road trips on the list, it’s more than worth it to visit Shawnee National Forest. In fact, plan to camp amidst the spectacular range of landscapes for one of the best driving trips from Chicago!

Local favourites include the Garden of the Gods – you’ll find super special rock formations like Anvil Rock. Little Grand Canyon and Bell Smith Springs feature moderate hikes; Inspiration Point offers panoramic views over the prairie, Mississippi River and the forest.

Not convinced? Shawnee Hills Wine Trail is a brilliant drive that links up vineyards and wineries in the area – a great stop on a road trip from Chicago.

How about driving from Chicago to Atlanta? Here’s my guide to the best stops on a Chicago to Atlanta road trip , just for you.

Best Chicago road trips in Winter

If you want the best road trips from Chicago when it’s colder and darker, then these are the best ones for you.

5. Grand Rapids

Distance: 3-hour drive

After just long enough of a drive, pull into Grand Rapids for a nice sweep of activities. The Beer City Ale Trail will keep you road-tripping on foot (or car, if you have a Designated Driver); or wander through Downtown Market for food adventures instead.

Warmed by booze, drop by the 158-acre Frederik Meijer Gardens & Sculpture Park where their installations are bright pops of colour against an all-white backdrop. 

6. Muskegon

Speaking of unusual winter activities, I’ve heard so much about Muskegon Winter Sports Complex. Just an hour from Grand Rapids, it’s a great next stop on your Chicago road trip.

Their Olympian-designed ice-luge course is perfect for beginners, spanning 850 feet of forested speed racing. Muskegon is also home to USS Silversides Submarine Museum if you’re into marine vehicles, and there’s a great pier and lighthouse too.

7. Indianapolis

When temperatures are cold, cold, cold – you might opt for staying indoors. The city of Indianapolis is one of the best road trips from Chicago during winter because of its incredible indoor entertainment: museums.

From the Indianapolis Museum of Art to the Indianapolis Children’s Museum to quirky Indiana Medical History Museum, you can escape the cold all day!

Of course, drop by famous City Market for great eats and then maybe go on a catacombs tour underground too. This makes for one of the best road trips from Chicago.

8. Boyne Mountain Resort

Distance: 5-hour drive

Michigan winters are best captured with the ski resort of Boyne. Drive past snowy landscapes to reach 850 acres of skiing, snowmobiling, dogsledding and photography escapades.

While the forested grounds offer romantic snow-covered views, don’t miss out on the epic zip lines that take you through the trees and slopes. 

If you like your road trips from Chicago with a bit of snow and ski thrown in, then this is a great option for you.

Your ESTA for the USA

Before you go to the USA make sure you have your ESTA organised. You can find help with this on this link: https://www.application-esta.co.uk/ESTA-guide . It doesn’t take long and organising it beforehand will make things go that bit smoother at the airport.

9. Apostle Islands

Distance: 7-hour drive

Does driving over ice count as going off-road?

It’s an unforgettable journey to Apostle Islands National Lakeshore as winter ice freezes thickly to transform water into road, ending with stunning ice caves!

Make sure to visit the only inhabited Madeline Island as well for a cool wind sled experience and hot tub stay. 

Day Road Trips from Chicago

10. lake geneva.

Distance: 1.5-hour drive

Chicago’s number one when it comes to day trips, Lake Geneva is one of the best lake town’s in the US.

Downtown boasts all the food and drinks you need for the inevitable food baby; you might even land a booze cruise.

Hot air balloon rides, Lake Shore Path, ziplines and even ski slopes make it a year-round place to visit. It’s a multi-visit destination for sure!

11. Harbor Country

Distance: 1-hour drive

Wind between the towns of Michiana, Grand Beach, Three Oaks, New Buffalo, Lakeside, Union Pier, Harbert and Sawyer. This Chicago road trip will have you hopping between wineries and breweries, not to mention the beach.

It’s so close to the city, but the sand dunes and soft grasses make it a wholly different world. 

12. Starved Rock State Park

Distance: 2-hour drive

Families and romantics will love Starved Rock State Park for reasons that include: 13 miles of hiking, 18 canyons, free entry and nature-surround lodge.

It’s a great location to unplug for a day as you hunt down natural rock pools, waterfalls and incredible moss-strewn glades. You can even visit in the winter for cross-country skiing and cuddles in front of expansive mountain views. 

13. Saugatuck 

Making up Lake Michigan’s “art coast of Michigan”, Saugatuck and its neighbours (Fennville and Douglas) are house dozens of art galleries!

Unique and LGBTQ+-friendly shops feature alongside artsy hubs to make it a super welcoming town. Of course, famous Oval Beach appeals with soft dunes and paddleboat rides too. From craft booze tours to fruit picking and corn mazes, it’s one of Chicago’s best road trips.

14. Elkhart Lake

I won’t spoil it for you but this 292-acre lake and nearby Kettle Moraine State Forest is truly a place to unwind from the crowds.

You can hike the epic Ice Age National Scenic Trail or bike down Old Plank Road Trail. Pumpkin patches, race-tracking and fishing are all inclusive!

Want a charming hideaway? This is it.

Road Trips 4 hours from Chicago

Want your road trips from Chicago for a special weekend? Then these Chicago road trips are only 4 hours away.

15. Ann Arbor

If you’re looking for an all-season destination, Ann Arbor is the perfect road trip from Chicago.

Huron River entertains with kayaking, paddle-boarding, tubing and swimming; Matthaei Botanical Gardens and Nichols Arboretum displaying beautiful foliage. Definitely spare some time for Kerrytown Market and Shops for all their indie offerings! 

16. Door Country

Also called ‘Cape Cod of the Midwest’, Door Country is a 70-miles-long basket of fun!

You’ll never get tired of exploring its orchards, coves, lighthouses and wineries. Away from the light pollution, Newport State Park offers stunning starlit skies while Ephraim is all the small-town charm you need. Just imagine – 300 miles of coastline.

You can reach Galena under 4 hours but I recommend taking your time. Pull up through scenic rolling hills to go back in time because the Galena Historic District is made up of cobblestone streets and over 1,000 buildings from the 19 th century.

For those non-history buffs, Chestnut Mountain opens as a ski resort in the winter; Stagecoach Trail and Apple River Canyon State Park are open year-round. 

18. Richland County

To really escape from people, Richland County is a rural road trip destination where you can bunk for the night. But away from the isolated and lush property of Candlewood Cabins are fields and hills that keep you outdoors all day.

The Ridge Road and Pine River Recreation Trail fulfils all your adventurous needs – where else would you find wildlife while biking over abandoned railroads?

You also have three rivers and five state parks within an hour’s distance, and the lovely 100-mile Lower Wisconsin River Scenic Byway for more driving way. 

19. Huron-Manistee National Forest

Michigan really surprises us again and again!

Along the peninsula is the expansive Huron-Manistee National Forest, one of the best road trips from Chicago if you are a nature enthusiast. A single paved road takes you through dense forest (beautiful in the fall) to parking areas so you can hike your way through the serene space or canoe on the rivers. 

Road trips from Chicago

Of course there are loads of great things to do in Chicago but visiting Chicago really opens up a world of opportunities when it comes to road trips.

Whether you’re taking the car out for an hour-long spin or you’re willing to buckle down for a few hours, you won’t be disappointed by the scenery along your journey or the fantastic destinations ahead. 

Related Posts:

• 7 Ways to Make the Most of Your Road Trip Budget
• Planning a Road Trip in the USA: 13 Best Routes!
• 57 Coolest Things to Do in Chicago for 2023
• Christmas Things to Do in Chicago in Winter: 21+…
• 14 Awesome Stops on a Chicago to New Orleans Road Trip
• 11 Unique Stops on the Drive from Chicago to Atlanta

Hi, I'm Vicky! I wrote this. You can find me on all the social media @VickyFlipFlop. I love a bit of adventure, will try anything once, and have a strong passion for the local food and drink, whatever it may be. I'm here to help inspire you to travel to places a little out of your comfort zone, or at least to explore the usual destinations in a different way. Stay, have a look around, and if you have any questions – let me know below.

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Your Family Will Love These 30 Road Trips Near Chicago

• Updated: 04/03/2024

Chicago and US Midwest families, we feel you. Airplane tickets are pricier than ever. Though, your need for a getaway has never been greater. 

You want to get out of town with minimal effort and do not want to spend a small fortune to do it. 

To help, I share my favorite short to medium-distance driving destinations and those recommended by regional experts—other travel bloggers and planners passionate about places in the Midwest. 

Together, we came up with this list of the 30 best road trip destinations for the summer and the fall, from big cities to small charming towns to blow-you-away natural wonders, all within a five-hour drive of Chicago.

Table Of Contents

Check out our destination recommendations by state below. 

• Michigan & Ontario

Or view all 30+ places we recommend going in the map below.

How to use this map:  In the map header, click the square tab to the left of my logo or click the enlarge frame to the right to view detail. You can save the map to “Your Places” on Google Maps by clicking the star next to the map name. Or you can share it by clicking the share icon.

Wisconsin: Top Road Trips Within 5 Hours of Chicago

Welcome to Wisconsin, or the “Dairyland State,” loved by visitors for its rich dairy heritage, delicious cheeses, and beautiful landscapes, including miles upon miles of lakeshore coastline.

Check out these six Wisconsin destinations shared in more detail below.

• Madison, WI
• Milwaukee, WI
• Sheboygan, WI
• Door County, WI
• Wisconsin Dells, WI
• Lake Geneva, WI

Also, consider adding Green Bay (a 4-hour drive) and the lake-perfect Northwoods towns of Manitowish Waters and Boulder Junction (a 5.5-hour drive) to your driving trip wishlists.

Madison, Wisconsin

Approximate drive time from Chicago: 2.5 to 3 hours

Recommended by: Rebecca Gade Sawicki of VeggiesAbroad.com

At just two and a half hours from Chicago, Madison is the perfect destination for a quick day trip or a weekend away . This sustainability-focused college town offers families tons of outdoor activities, diverse dining, and art and culture.

If you’re a family that loves the outdoors, visiting Madison during the summer is best. This is the prime time to enjoy the city’s prized lake life (five lakes surround it) and over 200 miles of paved bike trails. Madisonians love to bike (even in the winter), which is one of the best ways to see the city.

Another great activity to see Madison’s unique and eco-friendly side is to explore the independent boutiques that line Willy Street. You’ll find plenty of vintage shops, locally created art, zero-waste products, and clothing that’s been ethically produced and sourced.

While you’re in the area, don’t miss an iconic Madison treat, Nutkrack — this sweet and salty snack was actually created by accident! And, around the corner from Nutkrack is Madison’s oldest vegetarian restaurant , Green Owl Café — don’t miss their loaded vegan cheese fries.

When deciding where to stay in the city, the best place is downtown. This will put you within easy walking distance of many shops, restaurants, and events.

The Hyatt Madison/Downtown offers spacious rooms and suites, perfect for families, along with continental breakfast, and has multiple sustainability initiatives to reduce its and its guest’s carbon footprint. Or search for more Madison lodging options here .

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Milwaukee, Wisconsin

Approximate drive time from Chicago: 1.5 hours

Recommended by: Lisa of WavesandCobblestones.com

Milwaukee, Wisconsin , is the perfect city to visit on a family road trip from Chicago. Milwaukee is an easy 1.5-hour drive from Chicago, located to the north along the banks of Lake Michigan.

There are plenty of great things to do in Milwaukee to keep your family entertained! Rent kayaks and paddle along the Milwaukee Riverfront for some fresh air and exercise. Or show some team spirit and take the family to a ball game and watch the Brewers play baseball at the American Family Field or the Bucks on the basketball court at the Fiserv Forum.

There are many fun museums to visit in Milwaukee with your family, such as the Milwaukee Art Museum , a top-notch fine arts museum, where admission is free for children 12 years and younger. Or Discovery World , Milwaukee’s science museum, and Reiman Aquarium. Or the National Bobblehead Hall of Fame and Museum—a one-of-a-kind museum with over 10,000 bobbleheads from across the globe!

Stay at the Plaza Hotel , centrally located in Milwaukee’s historic Lower East Side, with suites that include a pull-out sofa and accommodate up to four people. The Plaza rooms have full kitchens, and with a large grocery store just a block away, you can save money on meals and snacks during your stay.

Or search for more Milwaukee lodging options here .

Sheboygan, Wisconsin

Approximate drive time from Chicago: 2.5 hours

Recommended by: Theresa Goodrich of TheLocalTourist.com

Sheboygan, Wisconsin, is a surprising destination only two and a half hours away from Chicago and a great road trip for families because of the variety of things to do. Begin your visit at the Visit Sheboygan Visitors Center and see Science on a Sphere , a suspended globe that acts as a projector screen displaying programs provided by the National Oceanic and Atmospheric Administration. You can also get tips for places to visit and pick up brochures and souvenirs.

One of the best things to do in Sheboygan for families is Bookworm Gardens. This whimsical garden is a haven for book lovers and children alike, where literature comes to life through vibrant displays and interactive exhibits. Another must-stop for families is the Above and Beyond Children’s Museum . You can’t miss it—there is a ship’s hull sticking out of the building! While downtown, stroll 8th Street for delicious pizza at Il Ritrovo , and don’t miss the Victorian Chocolate Shoppe . Since Sheboygan is on the shores of Lake Michigan, it is also a great summer vacation spot, with sandy beaches and lakefront parks .

Make Blue Harbor Resort your base camp. With its own waterpark, an arcade, mini-golf, a beach, and outdoor games—the kids will love staying at this resort. Or search for more Sheboygan lodging options here . 

Door County, Wisconsin

Approximate drive time from Chicago: 4 to 5 hours

Recommended by: Janice Moskoff of GatherandGoTravel.com

This Wisconsin peninsula just north of Green Bay, surrounded by Lake Michigan, boasts beautiful beaches, scenic hiking trails, and family-friendly activities that will keep everyone pleased for days. 

We visited Door County in the fall , and it was gorgeous. The leaves had not quite fully changed, though we took full advantage of the pretty outdoors to bike and hike at several of the peninsula’s five state parks . 

We even visited Cave Point County Park , one of the Door’s nearly 20 county parks, and were treated to an easy-to-access spectacular scene of Lake Michigan waves crashing against a stunning rocky coastline on a windy day. The beauty of this experience blew us away. Expect the Door to do the same to you.

In the summer, the Door truly shines. Families flock here for the beaches, events, and the abundance of outdoor activities. 

With over 300 miles of shoreline , you can swim, kayak, and fish in the crystal-clear waters of Lake Michigan, especially gorgeous on a sunny day.  Plus, the towns dotting the peninsula are charming, full of shops, galleries, and many restaurants.

Visit or stay on the west or bayside of the peninsula, where you can catch sunsets in towns like Fish Creek or Sister Bay . Or opt for the eastside—where we stayed—and catch the sunrises in or around Bailey’s Harbor . Top family-friendly resorts include Newport Resort , Ephraim Shores Resort , and Scandinavian Lodge . Though, know that the Door books early. So, if you plan your trip last minute, grab the best lodging you can get from Sturgeon Bay or further north and use it as a base to drive around and explore the Door. 

Search all family-friendly Door County lodging options on VRBO or Booking.com .

Wisconsin Dells, Wisconsin

Approx drive time from Chicago: 3 hours

Recommended by: Hannah & Adam Lukaszewicz of GettingStamped.com

The Wisconsin Dells is the ideal road trip destination from Chicago as it is known as the Waterpark Capital of the World . The driving distance from Chicago to Wisconsin Dells is just under three hours, making it the perfect length for a weekend getaway . Kids love to splash and play in the water, so why not visit multiple waterparks in one road trip?

The Wisconsin Dells is home to the first-ever indoor waterpark and currently has the largest concentration of waterparks in the world. No matter if you are visiting in the summer or the winter, you will find an amazing waterpark for your family to visit and enjoy, as the area is home to 12 different indoor water parks and over 20 water parks in total.

The best place to stay in Wisconsin Dells is one of the Waterpark Hotels . Our favorite waterpark hotel is Great Wolf Lodge as not only does it have a fantastic waterpark with a 6000 ft outdoor pool, 1000 gallon tipping bucket, a wave pool with three-foot-tall waves, a toddler pool, and a variety of slides for kids of all ages.

The Great Wolf Lodge has unique themed rooms and fun activities, including magi-quest, live shows, and an arcade, making it a kid paradise!

Lake Geneva, Wisconsin

Approximate drive time from Chicago: 2 hours

Recommended by: Diana of TravelsinPoland.com

With an approximate driving time of 2 hours, Lake Geneva is a short drive from Chicago and one of the best cities to visit in Wisconsin. The small-town atmosphere combined with a variety of activities make it a perfect choice for families with children of all ages.

Families can enjoy a day on the water, renting boats, kayaks, or paddle boards, or opt for a scenic boat tour around the lake. Or walk along a portion of the Lake Geneva Shore Path , a 21-mile trail that offers stunning views of grand estates and natural beauty. Spending time on the lake is the best way to experience the area, particularly during warmer months. Shopping in downtown Lake Geneva can keep families occupied for hours. The shops along the main roads have unique items such as art and handcrafted goods. There are also mom-and-pop cafes, ice cream, and candy shops in town.

For accommodation, The Abbey Resort , located in the heart of town, offers a great choice. It is a full-service family-friendly resort offering spacious rooms, indoor and outdoor pools, a game room for the kids, and a full-service spa for the adults. Or search for more Lake Geneva lodging options here .

Michigan & Ontario: Top Road Trips Within 5 Hours of Chicago

Experience the best of the Mitten State , a northern gem and a truly ideal destination for vacationing families. The Michigan coastlines—particularly to the west, with sandy beaches, spectacular sunsets, and towering dunes —will wow you with their beauty. Plus, the vibrant cities and small towns in Michigan will offer enough activities and culinary delights to keep you busy and satisfied for days.

Check out these four Michigan & Ontario destinations shared in more detail below.

• Saugatuck, MI
• Ann Arbor, MI
• Detroit, MI, into Ontario, Canada (a loop driving trip)
• Traverse City, MI (with a day trip to Sleeping Bear Dunes National Lakeshore)

To expand your options—consider adding these Michigan Southwest coastal towns to your road-trip-and-relax lists, like New Buffalo, St. Joseph/Benton Harbor, South Haven, Holland, and Grand Haven. Or spend time exploring more urban centers like Detroit or Grand Rapids .

Saugatuck, Michigan

Approximate drive time from Chicago: 3 hours

We love Saugatuck. We have visited for weekend trips several times in the fall and keep returning for more.  What draws us? The unbelievably beautiful beaches and dunes, the quaint downtown area filled with art galleries and boutiques, and the concentration of seriously elevated cuisine.

Our favorite beaches are Oval Beach , which consistently ranks as one of the top beaches in the country, and offers soft sand, clear water, and stunning views of Lake Michigan.  Additionally, we love the nearby and dog-friendly Saugatuck Dunes State Park , which is perfect for hiking and exploring, with over 1,000 acres of dunes, forests, and beaches.

When not visiting the beaches or getting ice cream, or shopping the galleries on Butler Street, Saugatuck’s main thoroughfare, we spend our time apple picking (in the fall), boating on the Kalamazoo River, or dining at one of the truly fantastic eateries in and around town. I share more things we love to do in Fall Trip: 10 Wonderful Family Things to Do in Saugatuck, MI “

Visiting families also love going on Saugatuck Dune Rides . This thrilling ride takes you on a tour of the dunes, with steep climbs and drops, which the kids will love. And bonus! The knowledgeable guides will share the history and ecology of the area, making it both fun and educational. 

For meals, you cannot go wrong nearly anywhere you choose to eat, but our favorites include The Southerner , where the biscuits alone are worth repeat visits, Pennyroyal Cafe & Provisions , and a short 15-minute drive to enjoy drinks and snacks at Virtue Cider .

Booking a stay in Saugatuck can be surprisingly pricey, so I share helpful information on where you can stay in the surrounding areas for less in “ Saugatuck, MI: 8 Amazing Areas to Search for Lodging .” Then, and especially because many local inns do not allow children as guests, I detail my top choices for family lodging in “ Roundup of the Best Family-Friendly Places to Stay in Saugatuck .”

Ann Arbor, Michigan

Approximate drive time from Chicago: 4 hours

Whether you’re a University of Michigan sports enthusiast or just looking for a hip town surrounded by gorgeous natural beauty, Ann Arbor is the ideal Michigan town to visit!  From Chicago, the trip via car or train (Amtrak offers service from Chicago’s Union Station to Ann Arbor) is just under four hours , making it a perfect road trip for a few days away!

Ann Arbor is well known for its thriving arts and culture scene . Year-round, it hosts a variety of art, music, and film festivals, including one of the largest outdoor art fairs in the nation, The Ann Arbor Art Fair . The Art Fair takes over Ann Arbor every July and spans 30 city blocks with over 1,000 artists! You’ll also find food and music throughout the fair.

For families who enjoy outdoor activities, you’re in luck! Ann Arbor is surrounded by natural beauty, with parks, nature reserves, and the Huron River flowing through it. Head to the Argo Livery during the summer and rent a canoe, kayak, or stand-up paddle board. You can go out on your own, or Argo offers multiple group river trips that range in time and distance from just under 4 miles and 1.5 hours to almost 6 miles and 2.5 hours.

When it comes to dining, you’re in for a treat — the city is well-known for its eclectic mix of cafes and restaurants. From the famous and funky sandwiches at Zingerman’s Delicatessen to the veggie eats at Ann Arbor’s best vegan restaurant, Detroit Street Filling Station.

When choosing a place to stay, it’s best to stay right in the heart of the city (especially if it’s your first visit). Two terrific family options include the Residence Inn by Marriott Ann Arbor Downtown and The Graduate Ann Arbor . Or search for more Ann Arbor lodging options here .

Detroit to Southwestern Ontario Loop Trip (a 5 Day, 4 Night Itinerary)

Approximate drive time from Chicago to Detroit: 4.5 hours

Recommended by: Erie Conners of EverywhereOntario.com

For a unique road trip that takes you into another country, consider making the trip from Chicago to Southwestern Ontario , Canada.  This southernmost region of Canada is filled with quaint small towns, sandy beaches , an abundance of fruit farms and wineries , and incredible historic sites that tell important stories from the Underground Railroad that delivered many slaves to freedom in the 1800s. 

From Chicago, you’ll drive 4 hours to the Detroit-Windsor border. In Detroit, you’ll cross the Ambassador Bridge or take the Detroit-Windsor Tunnel to get into Canada. 

Depending on how long you’ll be staying in Canada, here are the sites I recommend according to a path that takes you from the Detroit-Windsor border to the Sarnia-Port Huron border , where you’ll loop back to Chicago:

• Optional overnight at Caesar’s Windsor Hotel , or search for other Windsor lodging .
• Or, Pelee Island : Take the ferry to Canada’s southernmost landmass, Pelee Island. Visit Pelee Island Winery and bike around the island before taking the ferry home. Overnight in Leamington at a beautiful B&B , or other lodging . 
• Grand Bend Beach : Visit one of Ontario’s top beaches in the summer months. Lounge on the beach, participate in water sports, or walk along the Grand Bend Strip for boutique shopping.
• Sarnia: Walk along the waterfront to see Port Huron from the Canadian side. Overnight at The Insignia Hotel , in Sarnia . Or stay search for other nearby lodging .
• Cross the Bluewater Bridge back to Port Huron and drive 5 hours back to Chicago.

Traverse City, Michigan

Approximate drive time from Chicago: 5 to 5.5 hours

We visited vibrant Traverse City, MI , picturesquely nestled at the southern u-shaped end of Grand Traverse Bay , for five days in the heart of summer with our family dog and loved every minute of our trip. 

In addition to enjoying the lakeshore views that front the length of the town and strolling the shops and restaurants of bustling Front Street, our favorite activities were biking along the wooded TART trails—especially the Leelanau Trail, and hiking. 

We walked the paths in Grand Traverse Commons Natural Area , located behind the outdoor shopping plaza, making our way to the Hippie Tree, a massive old willow tree at the center of the trail network. Painted in bright colors by locals representing living artwork, the tree is rumored to have a haunted history that we only learned about after our visit. 

On another day, we drove out to the Old Mission Point Peninsula to spend the day enjoying the sweeping lake views from the lighthouse, hiking the trails in the adjacent Old Mision Point Park , stopping to buy fresh farmstand cherries, picking blueberries with the kids, and to enjoy a late al fresco lakeside lunch at the Jolly Pumpkin Restaurant & Brewery .

Another highlight was taking a day to visit the Sleeping Dunes National Lakeshore (a 40-minute drive), where we climbed dunes, hiked the Empire Bluff Trail , one of many in the area , and relaxed and picnicked on dog-friendly Esch beach. 

In addition to the outdoor activities, which could also include boat trips on Lake Michigan or kayaking on local lakes or rivers, your family will love the varied collection of breweries and wineries with outdoor dining areas ideal for families. When visiting, you can stay at a centrally located and family-friendly hotel, like the Bayshore Resort . Or search for a rental in the area. Find more available Traverse City hotels and lodging here . 

Indiana: Top Road Trips Within 5-Hours of Chicago

Hang out in the Hoosier State in one of these two top destinations:

• Indiana Dunes National Park, IN
• Indianapolis, IN

Additionally, consider staying in French Lick, IN, at the French Lick Resort  (a 5-hour drive), located in the hills of Indiana’s Hoosier National Forest. It is a classic family-friendly Americana resort offering loads of activities including, golf, biking, hiking, spa treatments, and supervised drop-off kid activities.

Indiana Dunes National Park, Indiana

Approximate drive time from Chicago: 45 minutes

Recommended by: Caitlin Dismore of TwinFamilyTravels.com

If you are in the Chicago area and looking for a family-friendly trip nearby, definitely consider visiting Indiana Dunes National Park and the surrounding area. Just 45 minutes outside of the city, the park offers a beautiful setting with plenty of beach access points and hiking trails.

In addition to the fabulous activities within the park, the surrounding towns offer a variety of attractions, shopping, and dining to keep the whole family entertained. West Beach is the perfect place for a family outing. It’s the largest beach in Indiana Dunes National Park and is great for swimming, sunbathing, or just relaxing. The Lake Michigan water is clean and clear, and there’s plenty of sand for kids to play with.

Hiking is another popular activity while in the park. Explore Indiana Dune’s biodiversity by hiking along the boardwalks, past historic homes, and even through marsh areas. If you are up for it, complete the 3 Dune Challenge at the nearby Indiana Dunes State Park .

If you are traveling with young children, consider staying at the Country Inn & Suites By Carlson Portage . The hotel has both a standard indoor pool and a shallow pool specifically designed for children, complete with a frog slide. Or search for other lodging options in the nearby Portage, Indiana area.

Indianapolis, Indiana

Approximate drive time from Chicago: 3 to 3.5 hours

This lively Midwestern city offers a wide range of activities and attractions ideal for families. From world-class museums to racetracks , expect a visit to Indy will be a memory-making trip your kids will love.

Top spots include the Indianapolis Children’s Museum , which has 472,900 square feet and five halls of exhibit space, making it the largest children’s museum in the world!  While there, kids can explore science, history, and art exhibits. Or they can ride a carousel, board a train, or climb a giant treehouse.

Prefer outdoor activities?  Be sure to visit the Indianapolis Zoo and White River Gardens , where the kids can roam, see amazing things, and do fun activities. In addition to seeing tigers, dolphins, and orangutans, the kids can visit the petting zoo, ride trains, join for animal feedings, or watch cheetah racing. 

For families who love cars and racing, include a visit to the Indianapolis Motor Speedway . Known as the “Racing Capital of the World,” the speedway is home to the famous Indianapolis 500 race and offers tours of the track and museum. When in the area, stop for burgers and root beers at the Mug ‘n Bun, a nearby vintage drive-in.

On where to stay, consider booking a room at the five-star Conrad Indianapolis tops the list with its spacious rooms and prime downtown location. Prefer something less splurgy? The more budget-friendly Homewood Suites by Hilton Downtown Indianapolis , with a complimentary breakfast, makes for an excellent alternative. Or search for other lodging options in the Indy area here .

Illinois: Top Road Trips Within 5-Hours of Chicago

Check out these top locations in the Land of Lincoln: 

• Starved Rock State Park, IL
• Shawnee National Forest, IL

Also, consider a visit to Galena (a 2.5 to 3-hour drive) with a historic downtown full of shops and restaurants, nearby outdoor activities like walking and biking along the Galena River, and lots of family-friendly lodging , some with pools.

Starved Rock State Park, Illinois

Recommended by: Alyssa of AnAppleaPlane.com

Only 1.5 hours by car outside the bustling city of Chicago, Starved Rock State Park transports visitors into another world. Dramatic canyons and cascading waterfalls are not the first things you picture when you think of the Midwest!  

If you do not plan to drive your own car, renting one will be most effective for your time and budget. Or, you can get to the area by taking a train from Chicago’s Union Station to Mendota Amtrak Station and hailing a 30-minute cab to the park. A huge draw to Starved Rock is its easy-to-access features . Many of Starved Rock’s most famous waterfalls provide drive-up parking lots, so the walk to the waterfall is only a couple of minutes.

Alternatively, consider parking at the main visitor center lot and hiking to your waterfalls of choice. Waterfalls at Starved Rock flow after rainfall or snow melt, so be mindful that these will not be here year-round. The longest-lasting waterfalls are at St. Louis Canyon and La Salle Canyon.

Other top features of the park include hiking, boat tours, and camping . And perhaps the park’s biggest draw—the entrance is free !

Consider staying in the highly-rated Starved Rock Lodge for either cabin or hotel room options. Or search for other nearby family-friendly lodging options here .

Shawnee National Forest, Illinois

Approximate drive time from Chicago: 5 hours

Recommended by: Melissa of HelloWanderlustFamily.com

Located in southern Illinois, Shawnee National Forest is about a 5-hour drive from Chicago, making it an easy and accessible destination for families. 

One of the best things about Shawnee National Forest is its variety of activities , such as hiking, fishing, ziplining, or just relaxing in nature—it offers something for everyone.  Two must-see attractions are Cave in Rock and Little Grand Canyon Trail. Cave in Rock is a 55-foot-wide cave formed over thousands of years by the forces of the Ohio River and the wind, and a highlight of Little Grand Canyon Trail is you get to hike in and around a series of waterfalls that cascade down the rocky cliffs. 

When looking for a place to stay, consider the location of your planned activities . Shawnee National Forest is huge, with some attractions only 15 minutes away, while others may take an hour to reach. Because of this, choose accommodation closer to the area where most of your activities will be. One excellent lodging option for families is Home2 Suites in Carbondale , which not only provides larger room sizes and access to a pool but is in a city that offers plenty of amenities. Or search for more Carbondale lodging options here . Alternatively, for a more unique and memorable experience, consider staying at the Timber Ridge Outpost & Cabins , which offers cozy treehouses perfect for families seeking a one-of-a-kind stay.

Gurnee, Illinois

Approximate drive time from Chicago: 45 minutes to 1 hour

Recommended by: Lisa of PlanningAway.com

If you are looking for a fun short road trip from Chicago, Gurnee Illinois is just the place! There are lots of fun things to do in Gurnee, Illinois !  Gurnee is about 45 minutes north of the city. Home to Six Flags Great America and Great Wolf Lodge , it is the perfect place to spend a fun weekend.   

Six Flags Great America is the highlight of a trip to Gurnee. There are over 30 roller coasters and rides to explore. There is also a water park inside Six Flags called Hurricane Harbor. Six Flags has great shows and entertainment options for all ages.  

To relax after a fun day at Six Flags, stay nearby at Great Wolf Lodge , where you can enjoy many activities, including an indoor water park, Magiquest game, rock climbing, ropes course, arcade, bowling, and mini golf.  Kids will also love character meet and greets, dance parties, and many other fun activities by Great Wolf Lodge, and included in your stay. The lodge is perfect for kids under the age of 12 . 

There are some places to eat inside Great Wolf Lodge, but if you want to really experience Gurnee, you will want to venture out and try some local favorites. Kaiser Pizza is delicious, and Oberweis Ice Cream is a must. Gurnee Mills shopping and outlet mall is a good stop for families too. Shop at the Bass Pro, eat at the Rainforest Cafe, and enjoy many more fun shopping options. If you do not want to stay overnight—Gurnee also makes for a great day trip from Chicago.

Missouri: Top Road Trips Within 5-Hours of Chicago

Saint louis, missouri.

Approximate drive time from Chicago: 4 hours 30 minutes

Recommended by: Lynli Roman of Wanderbig.com

With less than five hours between cities, Saint Louis is a family getaway that feels far away but is easy to drive from Chicago in a half-day! Book a room at the railroad depot turned hotel , Union Station , and spend your time exploring the many family-focused activities that Saint Louis offers.  First, take your family to explore the City Museum . Described as “weirdly wonderful,” the City Museum is the crown jewel of family-friendly fun in St Louis. Housed in an old shoe factory, the City Museum boasts a huge network of slides, tunnels, and caves for all ages. All ages love the rooftop, where you can ride the Ferris wheel or climb a giant praying mantis for perfect views of the St Louis skyline. 

Next, wander through Soulard Farmers Market and taste your way through the city. The Soulard Farmers Market is one of the oldest markets in the United States, with roots dating back to 1779! Most alive during the weekends, you’ll find 147 stalls filled with unique vendors selling everything from local Missouri produce to handmade gifts. Nearby grounds include a playground and plenty of space for an impromptu picnic with your market spoils. 

No family road trip to St Louis is complete without a trip to Forest Park— one of the nation’s largest and most-visited urban parks. The park is home to the Saint Louis Art Museum , the Saint Louis Science Center , the Missouri History Museum , an outdoor theater, and the Saint Louis Zoo . Entrance fees vary, but many amenities, including general admission to the zoo, are free!

Want to see more St. Louis lodging options ? Search for other family-friendly accommodation options here .

Ohio: Top Road Trips Within 5-Hours of Chicago

From city trips to world-class amusement parks to under-the-radar natural gems, Ohio regularly delights visitors , and especially families, with all it offers as a vacation destination.

Four Buckeye State destinations to consider for your next road trip include:

• Cincinnati, OH
• Cleveland, OH
• Cuyahoga Valley National Park, OH
• Cedar Point Amusement Park, OH

Cincinnati, Ohio

Approximate drive time from Chicago: 4.5 to 4.75 hours

Recommended by: Linda of MidwestExplored.com

If you’re looking for one of the best family road trips near Chicago—you can’t beat Cincinnati, Ohio.  After all, this underrated city is located just four and a half hours, or 297 miles, away from Chicago and is a well-priced, family-friendly destination brimming over with fun Cincinnati things to do that everyone will love.

So, start your visit with a trip to The Cincinnati Art Museum , founded in 1881, and in the Eden Park area.  Not only is the museum free to visit, but there are over 67,000 works that cover 6,000 years, ensuring there is something for everyone at this incredible institution. 

Next, grab a picnic lunch and explore Ault Park , which spans an impressive 220 acres of land and is the city’s fourth-largest park, and features a wealth of picnic areas, playgrounds, and walking trails that will help keep energetic kids busy. Finally, learn more about the Underground Railroad at the National Underground Railroad Freedom Center before taking in the electric hue of the cool signs on display at the American Sign Museum.

Then, when you’re ready to call it a day, return to your room at the Hyatt Regency Cincinnati , where you can take advantage of their family-friendly suites, indoor pool and catch up on laundry at their on-site facility. Or search for more Cincinnati lodging options here .

Cleveland, Ohio

A visit to Cleveland truly offers the best of all worlds—thrills at nearby Cedar Point Amusement Park (1-hour drive), cultural chills, and hills made for hiking at Cuyahoga Valley National Park (30-minute drive).  Stay in town at a place like centrally located and highly-rated Roost Cleveland , which offers fully furnished apartments with hotel-like perks,  and use it as a base to explore the area. 

The city, on the shores of Lake Erie, is home to the Rock and Roll Hall of Fame, the Cleveland Museum of Art, and the Cleveland Orchestra—great destinations and cultural institutions for families to experience and explore.  And when your crew gets hungry, head to the historic West Side Market to grab a bite from local food vendors and souvenir shop for artisanal products.

For families with outdoor enthusiasts, pair a visit to Cleveland with a day trip to Cuyahoga Valley National Park , a 30-minute drive away, where you can hike one of many highly rated wooded or waterfall trails.

Want to see more Cleveland lodging options ? Search for other family-friendly accommodation options here .

Cuyahoga Valley National Park, Ohio

Another must-see destination for families visiting Ohio is Cuyahoga Valley National Park .  Located just outside Cleveland (a 30-minute drive), this park offers over 33,000 acres of natural beauty and outdoor activities. 

Families can explore the park’s hiking trails , go fishing or kayaking on the Cuyahoga River, or even take a scenic train ride.  With its pretty waterfalls, wooded paths, and diverse wildlife, Cuyahoga Valley National Park is a perfect destination for families looking to get outside, get moving, and enjoy the best of what nature and national parks offer.  

If you do not plan on staying in Cleveland, consider booking rental lodging in tiny and historic Peninsula Village , a private island of town surrounded by Cuyahoga Valley National Park.  Top rental picks in Peninsula, OH, for families include a few three and four-bedroom homes that can sleep up to ten. Search “Peninsula, OH” on VRBO  to find them.

Cedar Point Amusement Park, Ohio

Approximate drive time from Chicago: 4.5 hours

Cedar Point Amusement Park , located on a peninsula extending into Lake Erie near Sandusky, Ohio, is surrounded by water and overflowing with family-style fun. 

Known as the “ Roller Coaster Capital of the World ” with over 70 rides, including 18 roller coasters—thrill-seeking families will love it. The park also features a water park, live entertainment, and plenty of family-friendly dining.  Take at least two days to enjoy all it has to offer.

Stay on-site at one of the Cedar Point resorts like the beachfront Hotel Breakers , Lighthouse Point offering cottages and campgrounds, Castaway Bay with an indoor water park, or the budget-friendly Cedar Points Express Hotel .

Kentucky: Top Road Trips Within 5-Hours of Chicago

Louisville, ky.

Need a reason to visit Louisville, KY? How about six? Your family will love visiting the Louisville Zoo or strolling along Waterfront Park facing the Ohio River and adjacent to downtown Louisville, stopping to play in playgrounds or cool down in hot summers at the splash park. 

While in the area, catch a ride on a riverboat like the Belle of Louisville , which offers several different types of cruises, including historic narrated ones to picnic lunch cruises . Or your whole crew might love the Hometown Music Kids Cruise , designed especially for families.

Kids and parents who love baseball—or love to see how things how are made—will enjoy a visit to the Louisville Slugger Museum & Factory , conveniently located downtown. Your tickets give you access to the museum and a tour of the factory—kids even get a free mini-bat at the end of the tour.

Need an indoor day activity? Explore the Mega Cavern , a former limestone quarry, now an underground adventure park offering ziplining, ropes courses, and a bike park, just a 15-minute drive from downtown and near the Zoo.  Or visit the downtown Kentucky Science Center , where your kids can engage with exhibits about the human body and outer space.

For places to stay, The Grady Hotel and Homewood Suites by Hilton Louisville Downtown are great choices. Both hotels are centrally located downtown and highly rated. Or search for more Louisville lodging options here . 

Related Reading

For traveling families, check out my related articles below for more trip ideas and tips that will help smooth your travels and get out the door with less hassle.

• Need An Itinerary For A Spring Trip To Europe? Here Are 25 Amazing Ideas
• 31 Warm Winter Break Vacation Ideas Your Family Will Love
• Enjoy the Ride: 12 Tips for Better Family Road Trips
• 15 Tips on How to Raise the Bar on Rental Cars
• Pack Faster & Better With This Universal Printable Packing List
• 25 Expert Packing Tips to Help You Travel Better
• Pre-Trip: A Practical Checklist to Close the House & Pack

Additional Trip Planning Resources

To further help you with travel planning, I share my go-to resources for every trip below. 

Google Flights. My first research stop for affordable flights for every trip. Learn why here . 

Google Hotels . Use its “ Where to stay ” button to discover the best neighborhoods to base your visit.

Booking.com. For hotel and rental bookings, I appreciate its flexible cancellation, candid user reviews, discounts, loyalty program, and easy-to-use interface.

Viator , Get Your Guide , & Airbnb Experiences . Quickly find and book highly-rated tours and activities on these sites.

Google Travel Things to Do & Google Maps . Find more things to do in your destination on Google Travel, then record where you want to visit on a custom Google Maps list. 

AllTrails . Love to hike? Me too. I religiously use AllTrails to discover hiking and biking trails and download its offline maps to manage my hikes.

Guide Along . 5-star self-guided audio tours that are GPS-compatible for US road trips and national parks. We loved the Glacier National Park tour .

Insure My Trip. I never travel internationally without trip insurance. Learn why here . My preferred place to shop and compare policies is InsureMyTrip.com . 

Plus, check out the 15 travel apps I use on trips, my preferred guidebooks , and my free customizable travel itinerary template , downloadable in four file formats.

About the author:  Janice Moskoff is a travel writer and blogger who loves hiking, exploring the world, and reading. She writes to inspire travel-loving families, adult friends, and couples on her blog,  Gather and Go Travel . Check out  her bio , learn how she became  a blogger , and discover how to  work with her . Sign up for her monthly  Discovery Newsletter  to get her latest travel recommendations and  how-to’s .

Love to travel? Sign up for m y monthly Gather & Go Travel Discovery Newsletter and get a free trip budget calculator .

Affiliate Disclosure: Some of the links on this page may be affiliate links, and at no additional cost to you, I earn a commission if you make a purchase. I only recommend products and companies I use. And the income goes to keeping the site community-supported and ads minimal.

From An Expert: InsureMyTrip.com is My #1 Pick for Trip Insurance

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39 Amazing Ideas for Things to See & Do in Missoula

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The Best Places to Stay Near Glacier National Park

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Welcome to Gather and Go Travel , a blog inspiring families, adult friends, and couples to explore US and international destinations and to get outdoors. I am Janice, an experienced traveler to over 50 countries and a travel writer, book lover, and blogger. Learn more about me , read our story , and how to work with me .

Need an Itinerary for a Spring Trip to Europe? Here are 25 Amazing Ideas

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The Best Road Trips From Chicago To Take This Spring

The best is yet to come, especially when you're going on an adventure. It's time to load up the car and head to one of these vibrant Midwest states for spectacular culture, art, and a culinary scene.

Fall is here, so it’s time to get away! While we adore our beloved Chicago, the Midwest is sprawling with beautiful and scenic cities within just a few hours of the city. Whether you want to get away to explore a stunning hiking trail or just spend the weekend roaming a charming town with cobblestone streets, there are tons of amazing things you can experience, so check out the best road trips from Chicago!

1. Madison, Wisconsin

First on our list is where Wisconsin’s capital is located, and it happens to be the second largest city in the state. Madison lies in the south-central part of the state and is centered on an isthmus between Lakes Mendota and Monona.

The proximity to the lakes makes waterside adventures a must; there are endless activities to participate in, between boating, kayaking, and swimming. After, take a stroll through the charming streets and head to one of the many breweries, or for an evening filled with serenity, head to the Olbrich Botanical Gardens , where Oblrich’s Thai Pavilion is located and is the only one in the US, and the only one outside of Thailand surrounded by a garden.

🚗 Distance from Chicago : 148 miles

🕐 Arrival Time: 2 hr and 23 mi

2. Holland, Michigan

When people think of Holland, what usually comes to mind is the Keukenhof Tulip Gardens in Amsterdam, Holland. However, you don’t need to buy an international plane ticket when another Holland is only a few hours away. This road trip from Chicago will be your new favorite getaway.

While in Holland, you’ll be able to indulge in Dutch experiences such as sprawling tulip gardens , cobblestone streets, and the picturesque Tunnel Park. With over 100 specialty shops, breweries, and restaurants, this is the perfect place to head on a road trip.

🚗 Distance from Chicago : 150.8 miles

🕐 Arrival Tim e : 2 hr 25 min

3. Traverse City, Michigan

One of our favorite Chicago trips, known as the “Cherry Capital” of the world, it’s easy to get lost in the beauty of Traverse City. Stroll along the shoreline at Grand Traverse Ba y and glance at the fluid waves as you take in a majestic sunset.

While there are many things to do in Traverse City, some of our highlights include touring the wineries, scaling a dune at the Sleeping Bear Dunes National Lakeshores, picking out some blum cherries, and immersing yourself in the beautiful lakeside town.

🚗 Distance from Chicago : 318.6 miles

🕐 Arrival Time : 4 hr 55 min

4. St. Louis, Missouri

One of the major cities in Missouri, St. Louis, lies along the Mississippi River and displays an iconic 630-foot Gateway Arch built in the 1960s. St. Louis is a quintessential city to visit, with a vibrant arts and culture scene, lively bars, and acclaimed restaurants.

This is also one of the best road trips from Chicago if you’re a fan of Chicago baseball. With Busch Stadium nearby, schedule your road trip for a game between the Cardinals and the Cubs, one of the best rivalries.

🚗 Distance from Chicago : 298.8 miles

🕐 Arrival Time: 4 hr 28 min

5. Bloomington, Indiana

Bloomington is most notably known as the home for students of Indiana University . Nestled in the rolling hills of southern Indiana, the city has spectacular foliage surrounding the town as you drive in.

Along with the visually stunning scenery , there is vibrant art, spectacular shopping, and notable restaurants—all of which support the thriving local business scene. However, it wouldn’t be right to mention Bloomington without mentioning sports. With the Big Ten, rowdy football and basketball games are an innate part of the town.

🚗 Distance from Chicago : 232.3 miles

🕐 Arrival Time : 3 hr 48 min

6. Columbus, Ohio

Along with Bloomington, Columbus is a celebrated city with a younger population due to the booming tech industry and innovative arts scene. As Ohio’s state capital , it’s one of the largest college campuses in the country.

This is one of the best road trips from Chicago if you’re looking for lively nightlife . Walking down High Street, you’ll be surrounded by reverberating music and packed patios, especially if the Buckeyes are playing.

🚗 Distance from Chicago : 356.5 miles

🕐Arrival Time: 5 hr 27 min

7. Wisconsin Dells, Wisconsin

Situated in southern Wisconsin, the Dells lies on the Wisconsin River in a region of glacier-carved sandstone formation and might be one of the most exhilarating cities on this lift. This is the best road trip near Chicago for any family planning an adventure-filled weekend .

There are numerous theme parks and entertainment centers, including Noah’s Ark Water Park and Mt. Olympus Water and Theme Park, both indoor and outdoor, spanned with waterslides, lazy rivers, rafts, and more! It’s one of the ideal road trips from Chicago for a family outing.

🚗 Distance from Chicago : 193.5 miles

🕐 Arrival Time : 2 hr 59 min

8. Saugatuck, MI

If you’re looking for award-winning beaches , scenic waterways, and verdant dunes, take a road trip to Saugatuck, Michigan. This is the ultimate escape for a quiet, luxurious weekend, with an animated art scene and renowned culinary restaurants. It’s a place that seamlessly switches from exploration to recreation for people visiting—making it one of the best road trips from Chicago.

🚗 Distance from Chicago : 145.8 miles

🕐 Arrival Time : 2 hr 19 min

9. Ann Arbor, MI

While many of the Michigan cities listed here are located along Lake Michigan, Ann Arbor is one the few recognized as an urban oasis in the middle of the state. The downtown scene is from a storybook with a red-brick main street filled with independent bookstores, locally-made candle shops, home goods, and more.

While there’s a lot to do downtown, head outside the city to explore the nature parks surrounding the town, which have some of the most scenic hiking trails.

🚗 Distance from Chicago : 241.3 miles

🕐 Arrival Time : 3 hr 45 min

10. Sheboygan, Wisconsin

Deemed the “Malibu of the Midwest, ” Sheboygan, Michigan, might not have five-foot waves like the West Coast. Still, it’s a freshwater haven for anyone who loves fishing, sailing, and surfing, from outdoor recreational activities like golfing and biking to events and festivals that highlight the art scene, cultural heritage, and vibrant music, it’s no wonder it’s one of the best road trips from Chicago.

🚗 Distance from Chicago : 147.6 miles

🕐 Arrival Tim e: 2 hr 24 min

11. Cincinnati, Ohio

Cincinnati is a beloved Midwestern city—right on the border of Northern Kentucky—some say it’s where metropolitan vibrancy meets Kentucky’s southern flair . From a wild sports fandom, you can catch Joe Burrow throwing a football or Joey Votto singing his bat, all less than a 1/2 mile from each other. However, besides athletics, there are splendid places to explore within Cincinnati, and it’s one of the ideal road trips from Chicago.

🚗 Distance from Chicago : 295.4 mi

🕐 Arrival Tim e: 4 hr 32 min

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6 Best Road Trips From Chicago

Waterfalls, storybook towns, incredible food, and more await just a short drive from Chicago.

Cities can sometimes feel like endless stretches of concrete — especially in the hot summer months — and Chicago is no exception.

Fortunately, there's a whole world out there beyond the city limits. While it doesn't always feel like it, there are so, so, so many worthy escapes within a few hours' drive of Chi-town: storybook towns studded with ice cream parlors, lakeside cities with entirely different cultures, and even places where you can connect with nature among waterfalls and lush trees. Waterfalls! Outside Chicago!

The Windy City's location, in this case, is your ally. Pack your car with some picnic accoutrements, and maybe some hiking gear just in case, and head off. You're within driving distance of some truly great, out-of-the-ordinary places that make for wonderful road trips. Here are six of them.

Madison, Wisconsin

Imagine a state already known for its beer and cheese having to cater to over 30,000 college students, and you've got some idea of the earthly delights that await in Madison, Wisconsin. This state capital could have been a destination in its own right for its unique geography — located on a narrow isthmus surrounded by two large lakes, it's beautiful even during cold Wisconsin winters — or its remarkable breadth of shopping, cultural events, and festivals, and architecture, but its food scene is virtually unrivaled for a city of its size.

The streets are filled with an eclectic mix of professors, politicians, businesspeople, street performers, and health nuts, and if you ask any of them for their favorite spot, you'll likely get a range of answers as large as the city's 250,000-plus population: American small bites at the new and renowned Mint Mark, tacos and margaritas at Canteen, Lao-Thai noodles from Vientiane Palace, and the list goes on and on.

Most students, however, will drive you toward craft-beer watering holes like The Malt House or Dotty Dumpling's Dowry, which purportedly serves one of the best burgers anywhere. Wash it down with some Wisconsin beer from New Glarus as well as some fried cheese curds, and you'll have yourself a real Madison, Wisconsin, night.

Madison is about two and a half hours from Chicago.

Starved Rock State Park, Illinois

Yes, Illinois isn't known for its natural beauty like some other states. Yes, its highest natural point is Charles Mound, a diminutive 1,235-foot hill. But that doesn't mean that hidden gems don't exist here. For a true escape from Chicago's steel-and-stone skyscrapers that is still within the state limits, drive to the area around Starved Rock State Park.

Visitors expecting more flat Illinois farmland will be surprised to find an incredible valley around the Illinois River, with lush trees, striking bluffs, and 14 gorgeous waterfalls feeding into the roaring waters. Starved Rock is a choice destination for camping, hiking, kayaking, and white-water rafting, and after you're exhausted from a day of physical exertion, it's also got a place to hang your hat: the Starved Rock Lodge .

However, if you feel like experiencing a bit more of the local flavor, the towns around the river valley provide it in buckets. Tiny, charming Utica is home to the August Hill Winery and some wonderful antique stores, while the historic towns of Oglesby and Ottawa are chock-full of Americana: small museums, galleries, and great food, particularly at the Red Dog Grill in Ottawa and The Rootbeer Stand in Oglesby.

Starved Rock State Park is about an hour and a half from Chicago.

Allegan County, Michigan

Lake Michigan is huge. And in the summertime, when the heat gets a little unbearable, you could easily just jump into the lake in Chicago. But there's something to be said for taking a jaunt out to Michigan to visit a string of lakeside towns that bring some truly unique qualities to the mix.

Douglas, Saugatuck, and Holland — and Fennville, though it's not right on the water — epitomize small-town charm, while still offering some truly city-sized amenities for city-sized appetites. Fennville is known as the fruit basket of Michigan, with apple orchards, vineyards, and berry farms alongside delightful creameries and even corn mazes, while Saugatuck and Douglas consistently take the cake as two of the best lakeside towns in the Midwest, with incredibly charming downtown areas, gorgeous undulating sand dunes, pristine blue water, and more art galleries than you can shake a stick at. In fact, it's here that two School of the Art Institute of Chicago instructors founded their own art school and residence, Ox-Bow, establishing an artists' colony right on the shores of Lake Michigan. Their legacy endures to this day.

Further up the road, you'll find a truly unique destination in Holland, where Dutch colonists established a foothold in the 1800s, bringing with them their culture, architecture, pastries (check out DeBoer Bakkerij), and even fields' worth of tulips, which you can find at Veldheer Tulip Gardens.

Fennville is about two hours from Chicago.

Indianapolis, Indiana

Among the many types of travelers out there — people who crave solitude, people who don't want to leave the 100-foot radius of their resort's pool — there are those who are fascinated by city life, jumping from one urban area to another. If you count yourself among them, a road trip from Chicago to Indianapolis is certainly warranted.

First off, it's the 15th-largest city in America, with a vast population and penchant for festivals, parties, and overall pageantry (it is the Racing Capital of the World, after all, and its famous month of May includes tons of smaller celebrations leading up to the Indy 500). No matter the time of year, though, you'll find Indianapolis in full swing, whether you're in the midst of its rollicking IndyFringe Festival in August and September or its Wine & Food Festival in June. It's also a museum hub, with the world's largest children's museum, several art museums with broad and granular focuses, and small museums focusing on its favorite children, from Vonnegut to President Benjamin Harrison.

But one of the main reasons visitors flock to Indianapolis is its incredible food scene, which has, in recent years, exploded into national prominence. Hot new restaurants like Bluebeard, Milktooth, Crispy Bird, Oca, and more have all contributed to its reputation as a gastronomical powerhouse, while iconic institutions like Workingman's Friend have been, well, working behind the scenes to keep Hoosiers well-fed for decades. It's about time their city gets noticed.

Indianapolis is about three hours from Chicago.

Traverse City, Michigan

If you're craving a real getaway, you can't do much better than northern Michigan — it's still within driving distance of Chicago and not as remote as the state's Upper Peninsula, while still providing a wilderness-tinged escape for city dwellers. The de-facto capital of the region, Traverse City, is a city in name, but its population of around 15,000 means it's got small-town charm and accessibility, making it a perfect gateway to the region's breathtaking sights. Stop in for a glass of beer or wine at one of the many famous wineries and brewpubs, like Mari Vineyards or Mackinaw Brewing Company, before heading into the wilderness.

From Traverse City's quaint streets, you can head north and explore the Leelanau Peninsula, or veer west to Sleeping Bear Dunes National Lakeshore. Better yet, take scenic M-22 to tick off both boxes. Sleeping Bear Dunes is one of the country's best stretches of shoreline, with incredible dunes and westerly views that mean it's got some of the best sunsets east of the Mississippi.

From there, mosey up M-22 to continue exploring the Leelanau Peninsula, where wilderness encroaches a bit further and small towns, each with a population under 1,000, dot the roads. Hike through the dense forests, pick apples and berries at the region's many farms, and be sure to grab a heaping sandwich from the Village Cheese Shanty in the county seat of Leland (population 377).

Traverse City is about five hours from Chicago.

Galena, Illinois

In rare cases, a road trip doesn't just mean traveling great distances — it can also mean traveling back in time. That's what's figuratively the case when you drive west from Chicago to Galena, consistently rated as one of the best small towns in America. For decades, Galena has been on a mission to preserve its rich history, meaning it has one of the most unspoiled historic town centers in the country.

The town's good fortune started back in the mid-1800s, when it was the beneficiary of government grants to begin mining precious minerals located under the town. Since then, the town has focused on maintaining the buildings from that boom time, and there are architectural landmarks around every corner. The Galena Historic District is a particular delight, comprising more than 1,000 buildings, including the home of Ulysses S. Grant, a prime example of the Italianate style and now a dedicated memorial to his legacy. The town even has trolley tours that take you to its major historical and architectural benchmarks, contributing to its overall throwback feel.

Galena's best eating institutions don't necessarily date all the way back to 1850, but that doesn't mean they aren't also great — Durty Gurt's Burger Joynt was founded in 2007 and serves gigantic, almost architecturally impressive stacks of meat and cheese. Looks like everyone's concerned with building a legacy here.

Galena is about three hours from Chicago.

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30 Delightful Road Trips from Chicago

If you’re looking to get away from the city, here are the best destinations for day trips and weekend road trips from Chicago.

Chicago’s location makes it an ideal place to get in the car and go, whether you live in the city or you make it your home base for some Midwestern exploration.

I’ve lived in Chicago and its suburbs for twenty years, and in the Midwest my entire life (except for a brief four years in my early twenties).

Let’s just say I’ve been to a LOT of towns, villages, cities, parks, etc., that are within easy driving distance from the Windy City.

And while I love Chicago (I even wrote a book about it ) and The Local Tourist began as a guide to the city’s River North neighborhood, sometimes even I just need to get away.

I’ve hand-picked some of my favorite Midwest road trips from Chicago. If you’re looking for delightful towns with delicious food and drink, boutiques and artisan shops, intriguing history, outdoor adventures, natural beauty, and so much more, you’re sure to find your perfect road trip from Chicago.

Road trips are the equivalent of human wings. Ask me to go on one, anywhere. We’ll stop in every small town and learn the history and stories, feel the ground and capture the spirit. Then we’ll turn it into our own story that will live inside our history. Victoria Erickson

Love travel quotes? Here you go!

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Road Trips from Chicago

How to choose the best road trips from chicago.

How far will you drive for a weekend trip?

I asked that question of members of The Local Tourist Facebook group and their answers surprised me. The winning time was five hours, and second place was four hours.

Several of these road trippers would even drive eight hours for a weekend vacation!

Based on their input, and my own obsession with road trips, I’ve included some destinations that require a few hours behind the wheel.

I’ve also included places that are much closer. In fact, there are a few towns and cities that are technically suburbs of Chicago. Depending on your starting point, these destinations may provide more of a staycation than a vacation.

But hey – that’s what being a Local Tourist is all about, right?

I’m only including destinations that I’ve personally visited and enjoyed. Clearly, I need to spend more time in Ohio and Michigan.

For each road trip destination, I’ve included driving time. This assumes you’ll be driving interstates and won’t be avoiding toll roads. It also assumes no traffic.

Depending on when you leave for your weekend road trips from Chicago, traffic could increase times by at least an hour, so check Google maps or Waze before you go.

I’ve also included suggestions for places to stay, as well as links to each destination’s official Convention and Visitors Bureau, or CVB. These local resources are my travel planning not-so-secret weapon .

Ready to plan your road trips from Chicago? Let’s go!

Related: before you go, check out all my tips for planning a road trip .

10 Day Trips from Chicago

If you’re looking for a quick getaway or even a day trip, these locations are short road trips from Chicago and all within two hours of the Windy City.

Elgin, Illinois

Driving time: 1 hour

Known as the City in the Suburbs, Elgin, Illinois, is a relatively quick drive or an easy train ride from downtown Chicago. Its proximity makes it perfect for a day trip, but there’s enough to do that you’ll want to make a weekend of it.

A good place to start is downtown Elgin. Located right on the Fox River, it’s filled with public art and historic buildings.

Get the history of the area at the Elgin History Museum (pictured above).

You can also take a free self-guided walking tour of the Elgin Historic District.

Since that walking will make you hungry, grab a sandwich at Blue Box Café or head up to West Dundee for a burger and a pint at Emmett’s Brewing Co., an award-winning brewery.

Another one of the great things to do in Elgin is visit Lords Park and Zoo. On its grounds is the Elgin Public Museum, the only natural history museum in the Fox Valley.

Where to stay in Elgin, Illinois: Most of the hotels in Elgin are along the I-90 corridor. The Holiday Inn & Suites is one of the most highly rated accommodations near Elgin.

CVB: Explore Elgin Area, exploreelginarea.com

Indiana Dunes National Park, Indiana

One of our newest national parks is a short drive or train ride from Chicago. Established in 2019 , Indiana Dunes National Park is 15,000 acres along the southern shores of Lake Michigan.

There are over fifty miles of trails, making hiking Indiana Dunes National Park one of its top attractions. Hikers can traverse dunes, wetlands, prairies, rivers, and forests, all in one park.

There’s a fee to access the park: $15 per person (up to $25 per family group) and $25 per carload.

You could spend the entire weekend at the park. However, if you want a break, drive a little further east to Michigan City.

While the town is known for Lighthouse Place Premium Outlets, it’s also home to several museums, including the Old Lighthouse Museum.

Where to stay near Indiana Dunes State Park: Camping is available within the park itself, and there are several hotel chains in Michigan City .

CVA: South Shore Indiana, southshorecva.com

Harbor Country, Michigan

Driving time: 1 hour 15 minutes

Just across the border from Michigan City, Indiana, is Harbor Country.

The Red Arrow Highway takes you through eight small towns, each unique, each charming in its own away. Think boutique instead of big box, locally owned versus chain.

Outdoor enthusiasts will find everything from kayaking and paddle boating to fishing, surfing, and golf. Of course, you can also spend the day at the beach.

One of the biggest attractions is the number of Southwest Michigan wineries and breweries. The climate is very similar to Napa Valley, and the area’s known for its award-winning wines.

Where to stay in Harbor Country: You can find inexpensive hotels as well as private homes in New Buffalo, Michigan .

CVB: Harbor Country Chamber of Commerce, harborcountry.org

Kenosha, Wisconsin

Driving time: 1 hour 20 minutes

Kenosha is the fourth largest metro area in Wisconsin, as well as the fourth-largest city on the shores of Lake Michigan, and there are TONS of things to do.

It’s the home of the oldest operating velodrome in the country, a free dinosaur museum, historic restaurants, not one but two lighthouses, and you can still ride an electric trolley.

Start your visit at the Kenosha History Center for an overview of the area’s past. Then don’t miss the Dinosaur Discovery Museum or Kenosha Public Museum, both of which are free.

The Civil War Museum is an impressive look at Wisconsin’s role in the war.

A must-visit restaurant is House of Gerhard, featuring traditional German specialties. Another favorite is Franks Diner. Guy Fieri featured it on  Diners, Drive-ins, and Dives and it serves up tasty American cuisine with a side of sass.

Check out more reasons you should visit Kenosha, Wisconsin .

Where to stay in Kenosha: you can stay in Kenosha hotels that are conveniently located off I-94, or you can choose an historic inn like The Stella Hotel and Ballroom. For a great view, check out Wyndham Garden Kenosha, right on the harbor.

CVB: Visit Kenosha Wisconsin, visitkenosha.com

McHenry County, Illinois

Driving time: 1 hour 30 minutes

I lived in McHenry County, whose northern border is shared with Wisconsin, for five years and still found new things to do.

One of the most surprising aspects of the area is the sheer number of parks. The McHenry County Conservation District manages more than thirty conservation areas, and most of them have hiking trails.

There are also city and village parks, as well as two state parks within the county.

Another great thing about the area is the food. Oh, the food! There’s farm-to-table at 1776 Restaurant and Duke’s Alehouse and Kitchen, incredible Italian at 750° Cucina Rustica, rich encased meats at Richmond Brathaus, and the best custard anywhere at Julie Ann’s Frozen Custard.

All are local; all are family-owned; all are delicious.

McHenry County’s county seat is Woodstock, which you might recognize. It’s where Groundhog Day was filmed, and the town celebrates with their very own groundhog, Woodstock Willie.

You can even stay in the same bed and breakfast where Bill Murray’s character woke up again, and again, and again.

With the mouthwatering breakfasts served each morning at Cherry Tree Inn Bed and Breakfast, though, you won’t mind if the same thing happens to you.

Read more about why I love being a Local Tourist in McHenry County , and you will, too!

Where to stay in McHenry County: Cherry Tree Inn Bed and Breakfast , of course! Since there are only four rooms, if they’re full, you can find hotels in Crystal Lake , the largest town in the county.

CVB: Visit McHenry County, visitmchenrycounty.com

Starved Rock State Park

Head to Starved Rock State Park for a day of fresh air, physical fun, and outdoor adventure.

Located just 94 miles southwest of Chicago, the landscape is an unexpected tableau of bluffs, steep trails, and waterfalls. Since it’s on the Illinois River, there’s also fishing and boating.

You can bring a lunch to enjoy at the waterfront picnic area, or grab a bite to eat at the historic lodge.

Nearby Ottawa is a charming town with lots of creative chefs, so you can have the best of both worlds.

Where to stay in Starved Rock State Park: There’s a lodge at the park itself, but I personally prefer camping. Starved Rock has one of the best campgrounds in the Midwest .

Janesville, Wisconsin

Driving time: 1 hour 45 minutes

Located right off I-90, Janesville is an ideal weekend road trip from Chicago, especially if you like the great outdoors, art, and history.

The town’s tagline is “Wisconsin’s Great Outside,” and there are thirty miles of trails in Janesville, including a portion of Wisconsin’s Ice Age Trail. One of the most scenic treks is the mile and a half hike to Devil’s Staircase.

The Rotary Botanical Gardens is a non-profit garden covering twenty acres. You won’t want to miss their Holiday Light Show.

From Thanksgiving weekend through December, the gardens become a magical winter wonderland strewn with hundreds of thousands of lights.

History buffs will get a kick out of exploring Janesville’s thirteen historic districts. One of the highlights of any visit to Janesville would be the Lincoln-Tallman House.

Built in 1857, it’s been a museum since 1951. Eighty-five percent of the furnishings in the house are original, including the bed that Lincoln slept in when he was a guest.

Janesville’s dining scene is relatively new, but with restaurants like Genisa Wine Bar and the Sandwich Bar, it’s gaining steam and there are enough unique spots to keep your palate happy.

I definitely recommend bellying up to the 1933 Art Deco bar at O’Riley and Conway’s Irish Pub for some Scotch eggs.

Combine history and beer at Gray Brewing Co. They’ve been brewing beer since 1856, except during that pesky Prohibition when they turned to sodas. It’s one of the oldest family-owned breweries, not just in Wisconsin, but in the United States.

When you visit Janesville, make sure you’ve got your walking shoes and plenty of room on your SD card, because the town is filled with vibrant and colorful murals.

Where to stay in Janesville, Wisconsin: Renovated in 2019, the Hampton Inn provides comfortable rooms with modern décor. Breakfast is included, and it’s one of the better spreads I’ve seen.

When I stayed, the hot items were frequently replenished and there were several options including both waffles and mini-waffles.

CVB: Janesville Area Convention and Visitors Bureau, janesvillecvb.com

Lake Geneva, Wisconsin

Located just 75 miles northwest of Chicago on the other side of the Wisconsin border, Lake Geneva provides a year-round escape from hectic city life and is a short day trip from Chicago or great weekend destination.

One attraction with a direct tie to Chicago is the Yerkes Observatory (pictured above).

Yerkes is considered the birthplace of modern astrophysics and was funded by Charles Yerkes, who had a huge role in developing Chicago’s public transportation.

Lake Geneva has long been a playground for Chicagoans. In the late 1800s and early 1900s, it seemed that every wealthy Chicagoan built a mansion on the shores of the lake. Today, many of those mansions still stand.

The best way to see them is to take a boat tour, especially if you can ride along when they’re delivering the mail. Lake Geneva is one of the few places left in the country where mail is delivered by boat.

Another way to see the mansions is to walk the path that surrounds the lake. Like Chicago’s lakefront with its public beaches, Geneva Lake is surrounded by a trail that’s open to everyone.

The lakefront path is one of the most popular things to do in Lake Geneva .

One place you can only visit from a boat, unless you have physical limitations and can’t climb the many stairs from the dock, is Black Point Estate. This historic mansion has many ties to Chicago, including Jane Addams .

For something completely different, feed an ostrich. Safari Lake Geneva is a drive-through experience that allows you to feed giraffes, alpacas, elands, and emus.

An experience that’s both fun and tasty is taking a class at Lake Geneva Cooking School. Chef John teaches you how to make dishes you might never attempt on your own, and he pairs them with stellar wines.

Like many, during lockdowns he pivoted and fulfilled his dream of publishing a cookbook . I’ve made several recipes from it, and highly recommend it.

Golf is one of Lake Geneva’s biggest draws. During the winter months, you can ski, snowboard, snowshoe, and ice fish.

Where to stay in Lake Geneva: Technically located in Fontana on the west side of Geneva Lake, The Abbey Resort is a sprawling complex with beautiful rooms overlooking a marina.

They also have multiple pools and there’s often live music, either in the bar or outside during the summer.

CVB: Visit Lake Geneva, visitlakegeneva.com

Milwaukee, Wisconsin

Milwaukee, Wisconsin, is an urban getaway filled with culture and outdoor fun.

The instantly recognizable Milwaukee Art Museum is definitely worth visiting, and after you’ve browsed its collections you can take a walk along the lakefront.

For more art, book a room at Saint Kate The Arts Hotel . This astounding hotel is like staying in a work of art – because you are. It’s right downtown, providing easy access to the river walk.

Beer lovers will have a blast exploring Milwaukee’s breweries. Lakefront Brewery is known for its fun tours. Milwaukee Brewing Company and Mobcraft are also great places to visit.

There’s no beer at the Pabst Mansion, but you’ll still want to see Captain Frederick Pabst’s house, built in 1892. It’s a gorgeous Flemish Renaissance Revival mansion that’s on the National Register of Historic Places.

Fun fact: Captain Pabst earned his stripes with the Goodrich Line of steamships, which was based out of Chicago.

Another nautical stop is North Point Lighthouse. Built in 1888 high on a bluff, Frederick Law Olmsted himself designed the grounds. Chicagoans will recognize the famous landscaper’s name from the 1893 World’s Columbian Exposition and the University of Chicago, among others.

Olmsted also landscaped Lake Geneva’s Yerkes Observatory, which was part of the University until recently.

The Harley-Davidson Museum is another must-stop and be sure to dine at Motor, the on-site restaurant.

During the summer there are festivals just about every weekend, so check Visit Milwaukee’s events calendar to find out what’s happening.

And of course, make sure you have some cheese curds, brats, and beer.

Where to stay in Milwaukee: Saint Kate The Arts Hotel for a modern art experience, The Pfister Hotel for a dose of history, and Iron Horse for more industrial décor and easy access to the Harley-Davidson Museum.

CVB: Visit Milwaukee, visitmilwaukee.org

Lafayette, Indiana

Driving time: 2 hours

My grandparents lived in West Lafayette, Indiana, so I grew up visiting. However, it wasn’t until a few years ago that I actually explored the town. Boy, had I been missing out on a lot.

Known as the home of Purdue University, West Lafayette, and its sister city Lafayette, have history, art, culture, delicious food and drink, and a vital sense of community.

There are several places that make this a great place for a road trip from Chicago. One is the Haan Mansion Museum of American Art.

The mansion was originally built for the 1904 World’s Fair in Saint Louis. Now it’s in West Lafayette and is filled with impressionist paintings and historic furniture.

Another is SAMARA. Designed inside and out by Frank Lloyd Wright for Dr. John and Catherine Christian, it’s a nearly perfectly preserved example of Wright’s Usonian architecture.

Another fascinating spot is Prophetstown State Park, combining a landscape that’s distinctly Indiana with the history of the Native Americans who fought the settlers’ encroachment, and the farmers who eventually tilled the land. While there, visit the nearby Tippecanoe Battlefield.

I’ve got even more places to visit in Lafayette. These include not only places I’ve been, but also spots recommended by students at Purdue University. I’ve partnered with a 400-level travel-writing class since 2018, and many of their submissions are local to the college town.

See why you should visit Lafayette and West Lafayette Indiana

Where to stay in Lafayette, Indiana: Mr. TLT and I loved the cozy intimacy of Black Blanket Farms Bed and Breakfast . If they’re booked, Lafayette has a gazillion hotel options since it’s a college town.

CVB: Visit Lafayette-West Lafayette, homeofpurdue.com

9 Weekend Road Trips from Chicago between 2 and 3 hours

Shipshewana, indiana.

Driving time: 2 hours 15 minutes

If you’re looking for a slower pace, yet still want plenty to do, add Shipshewana to your weekend adventures.

Shipshewana is in LaGrange County, also known as Indiana Amish Country. You’ll know when you get close because you’ll start seeing horse-drawn buggies and bicyclists everywhere.

With the third largest Amish population in the world, this area is a definite departure from the hustle and bustle of city life. Instead, it’s antiques and hand-crafted furniture, delicious food, and fun entertainment.

One of Shipshewana’s most well-known attractions is the Shipshewana Flea Market . Begun in 1922 with a livestock auction, this family-owned business is the largest flea market in the Midwest.

Learn what it’s like to attend the Shipshewana Misc & Antique Auction .

You also don’t want to miss the Davis Mercantile . Another family affair, it’s a destination for dining, shopping, and riding the carousel.

If you plan your trip in advance, you might be able to dine in an Amish home, which is a real treat (and the best mashed potatoes ever). If it’s a last-minute getaway, The Blue Gate Restaurant is always a favorite. After dinner, head upstairs for a show at the theater.

Other fun things to do in Shipshewana include touring Cook’s Bison Ranch, exploring one of the many county parks, having dinner in an Amish home , canoeing or kayaking on the Pigeon River, and taking a driving tour on a hunt for barn quilts.

Where to stay in Shipshewana: The Blue Gate Garden Inn is a comfortable hotel that’s filled with amenities, including outdoor fire pits and an ice cream shop.

CVB: Visit Shipshewana, visitshipshewana.com

Sheboygan, Wisconsin

Driving time: 2 hours 30 minutes

When people ask me the destination that surprised me the most, Sheboygan, Wisconsin, tops the list.

I visited in August 2021, and it was my first press trip post-cancer. It was exactly the experience I needed: waves, beaches, amazing food, brilliant art, and a community that preserves its past.

Your first stop should be the Sheboygan Visitor Center. It is absolutely the coolest visitor center I’ve ever seen – and I’ve been to a lot.

Sheboygan’s known as the Malibu of the Midwest, so of course I had to get out on the water. One of my favorite things to do was take a first sailing lesson in Lake Michigan. That’s right – you can learn how to sail on a weekend trip to Sheboygan.

The Kohler name is prominent in the area. In addition to the manufacturing company and a nearby resort, there’s also the Kohler Arts Center and the Kohler Art Preserve, which opened in 2021.

Kohler also manages the James Tellen Woodland Sculpture Garden, one of several artist-built environments throughout the state.

History geeks will want to stop at Sheboygan Indian Mound Park and the Sheboygan County Historical Society and Museum.

For dining, don’t miss Black Pig, Il Ritrovo, and BoMallies. Breakfast should absolutely begin at Paradigm Coffee and Music. Best. bagel. sandwich. ever.

Check out my piece about this surprising place, and I’ve even included the perfect 3-day Sheboygan itinerary .

Where to stay in Sheboygan: Blue Harbor Resort offers gorgeous rooms and an even better view. They’ve also got a whole water park, on-site dining, and easy access to the beach.

CVB: Visit Sheboygan, visitsheboygan.com

Elkhart Lake, Wisconsin

About twenty minutes from Sheboygan is another delightful road trip from Chicago.

Elkhart Lake has all the feelings of a resort town. There are historic accommodations, unique boutiques, and delicious dining.

The eponymous lake is gorgeous, with crystal clear water. You can take a pontoon boat ride, or go kayaking or paddle boarding.

The village is also right by the Ice Age Scenic Trail and Kettle Moraine State Forest – Northern Unit, providing lots of opportunity for outdoor activities.

Racing fans won’t want to miss Road America. This four-mile road course is considered the best in the United States and one of the top in the world.

Not only can you watch racing, you can also take a spin around the track yourself. They offer both motorcycle and automobile driving schools.

Where to stay in Elkhart Lake, Wisconsin: Osthoff Resort is an historic inn that offers a variety of room options, including suites and villas, and features amenities such as an indoor and outdoor pool, spa, and fitness center.

The resort also has several dining options on-site, including a fine-dining restaurant and a casual bistro.

CVB: Elkhart Lake, visit website

Galena, Illinois

Driving time: 3 hours

Galena, Illinois, is located near the Mississippi River on the opposite side of the state from Chicago. Surrounded by the rolling hills and bluffs of the Driftless Region, it’s an area dotted with wineries and golf courses.

There are many reasons nearly a million people visit the former mining mecca each year. From shopping along its historic main street to the many wineries in the area, it’s a great spot for a romantic weekend or a girls getaway.

A stroll down Main Street feels like a step back in time. Be sure to stop into Galena Canning Company for a taste of salsas and jams, and Galena Brewing Company offers a lineup of tasty beers.

Thrill-seekers will love a visit to Long Hollow Canopy Tours , a zipline adventure through the woods.

Nature lovers can explore trails along the nearby Mississippi River, and golfers will love a few rounds at Eagle Ridge Resort & Spa.

There are also several historic buildings, and the Ulysses S. Grant Home is one of the most popular places to visit for a look into the past.

Where to stay in Galena, Illinois: While there are hotels that are closer to Galena’s historic Main Street, two of my favorites are a short drive from downtown. Goldmoor Inn Bed and Breakfast is an elegant getaway overlooking the Mississippi River.

Eagle Ridge Resort and Spa is my home away from home when I’m in Galena. I’ve stayed there at least five times. I love the variety of accommodations, activities, and the delicious food.

CVB: Visit Galena, visitgalena.org

Hendricks County, Indiana

My first visit to Hendricks County, Indiana, was in 2017, and since then I’ve returned four? five? times. You might say I like it. I even taught the first writing workshop for Midwest Travel Network (I’ve now taught three) at Natural Valley Ranch, a cabin with that private pond out its back door.

There are also horses, that you can ride. Squeee!

It’s a large county comprised of several towns. Some are large, like Plainfield and Avon, and others are small, like the tiny Lizton, which is home to the best barbecue – and pecan pie – in Indiana (and possibly the Midwest).

Race fans not only have easy access to the Indianapolis Motor Speedway, they can also see the NHRA Finals at the Lucas Oil Raceway within Hendricks County.

The only Doctor Who Museum and Store is in Hendricks County, as is the Tie-Dye Lab, where you can make your own tie-dye apparel. Beasley’s Orchard has the best apple cider. Oasis Diner is the only diner on the National Road and it’s got one of the best pork tenderloin sandwiches anywhere.

Basically, go to Hendricks County . There’s so much to do I bet you’ll want to go back again and again, just like I do.

Where to stay in Hendricks County: Natural Valley Ranch is great if there’s a big group of you exploring the area. If not, then I’m a fan of Staybridge Suites . Each room includes a kitchenette, plus they offer free breakfast and weekday happy hours.

CVB: Visit Hendricks County, visithendrickscounty.com

More Road Trips from Chicago between 2 and 3 hours

• Madison, Wisconsin; 2 hours 45 minutes
• New Glarus, Wisconsin; 2 hours 45 minutes
• Indianapolis, Indiana; 3 hours
• Quad Cities, Illinois/Iowa; 3 hours

11 Weekend Road Trips from Chicago between 3 and 5 hours

Fort wayne, indiana.

Driving time: 3 hours 10 minutes

When you go to Fort Wayne, go hungry. And thirsty. This northeastern Indiana town has a thriving food and beer scene that will have you coming back for more.

This All-American City is located at the confluence of three rivers, and that riparian location has fed its personality since it was founded when General “Mad” Anthony Wayne built a fort there in 1794. That fort didn’t last long, and by 1815 the town was on its third fort, built by Major John Whistler.

Chicagoans might recognize that name: he built Fort Dearborn when he was a Captain. You can visit a replica of Whistler’s fort, and they often have events.

One of the best things to do in Fort Wayne is visit the YLNI Farmers Market. This bustling marketplace features everything from handmade chocolates to hot sauces that’ll blow your top off to candles that smell like Fort Wayne (and Montana, Chicago, and everywhere else Simple Nature‘s creative creator has been). 

But what about that food, you ask? A few favorites include Club Soda, for white tablecloth dining with a side of live music, Birdie’s for shared plates in an airy rooftop, and Hall’s Prime Rib for down-home diner cooking.

Beer fans will want to belly up at Junk Ditch, The Hoppy Gnome, and Hop River Brewing Company.

Where to stay in Fort Wayne, Indiana: Courtyard Fort Wayne Downtown at Grand Wayne Convention Center is in a great location; across from the convention center and in between Parkview Field and Embassy Theatre.

CVB: Visit Fort Wayne, visitfortwayne.com

Green Bay, Wisconsin

Driving time: 3 hours 15 minutes

While it may seem blasphemous to some to suggest driving to the home of the Packers from the home of the Bears, I guarantee there’s a lot more going on than gridiron battles.

Auto enthusiasts will love The Automobile Gallery. Opened in 2016, this collection of pristine vehicles span over a century of automotive history.

From the iconic 1908 Cadillac Model T to the sleek 1960 Chevrolet Corvette, every car enthusiast will find something to admire.

The museum also features a rotating selection of vehicles, ensuring that there is always something new and exciting to discover.

For transportation of another kind, visit the National Railroad Museum. The museum began in 1956 and now covers a sprawling 33-acre campus.

Not only can you see locomotives like the iconic “Big Boy” No. 4017, you can step inside a Pullman sleeper car and learn about the porters who worked America’s rail lines.

Ready for a drink? From Captain’s Walk Winery to Zambaldi Beer, you’ll find something to whet your whistle.

And if you’re hungry, Green Bay will keep you fat and happy. (Speaking from experience here.) Don’t miss the authentic kringles at Uncle Mike’s Bake Shoppe or a cup of Booyah, a hearty Belgium chicken stew.

Where to stay in Green Bay, Wisconsin: Stay in the heart of Green Bay at the historic Hotel Northland . The hotel’s especially great for a romantic getaway.

CVB: Discover Green Bay, website

Dubuque, Iowa

Driving time: 3 hours 20 minutes

You’ll be glad Dubuque Iowa is one of these easy road trips from Chicago, because there’s so much to do you’ll want to return again and again.

Dubuque’s location on the Mississippi means it’s filled with river lore. Begin your visit at the Mines of Spain, a National Historic Landmark and Iowa State Recreation Area. It’s named for the mines that Julien Dubuque, the town’s founder, worked with permission from first the Mesquakie and then the Spanish. The Julien Dubuque Monument resembles a rook and overlooks the Mississippi; Dubuque is buried on the site.

Get an in-depth introduction to the river and the region at the National Mississippi River Museum and Aquarium, then go on the river itself. You can take a steamboat tour or an American Lady River Cruise aboard a yacht.

Like Janesville, Dubuque’s downtown is also covered with murals, and it’s a fun afternoon to walk the streets and find your favorite.

Dubuque’s most unusual attraction is the Fenelon Place Elevator. It’s the shortest, steepest railroad and a ride to the top provides some of the best views in the city.

Another spot for great views is Eagle Point Park. You’ll get a birds eye view of Lock and Dam #11 and can see into both Wisconsin and Illinois.

One of the most famous attractions is in nearby Dyer. The Field of Dreams Movie Site is surprisingly moving, especially now that you can tour the house. Inside you’ll discover stories behind the filming of this beloved classic.

I think the food scene in Dubuque will surprise you. It certainly surprised me to discover several innovative chefs serving quality cuisine. Make reservations for both Brazen Open Kitchen and Pepper Sprout and you’ll be one happy diner.

Where to stay in Dubuque, Iowa: since it’s right downtown, you can’t get much more convenient than Hotel Julien Dubuque . Plus, it’s a gorgeous hotel with oodles of history, including stories about Mr. and Mrs. Lincoln and a certain gangster from Chicago.

CVB: Travel Dubuque, traveldubuque.com

Brown County, Indiana

Driving time: 4 hours

Brown County, Indiana, is known for its beauty when the leaves change colors, but that doesn’t mean you can only visit in the fall. The rolling hills are beautiful year round.

While the area is easy to get to now, that wasn’t always the case. Its relative isolation fostered a vibrant artists community, which thrives to this day.

Visit Brown County and you can see the home and studio of one of the founding artists T.C. Steele. He was one of the five members of the acclaimed Hoosier Group. In the late 1800s, that group put Indiana’s art scene on the map, and Brown County in particular.

Browse the galleries of Nashville, Indiana, and you’ll see works of art from those early painters as well as artists of today.

Get a two-for-one cultural experience at Country Heritage Winery. Not only can you taste wines, when you take a weekend road trip from Chicago, you can do so while listening to live music.

Another favorite is Hard Truth Hills. Inspired by Sierra Nevada’s set-up in Asheville, North Carolina, this is a multi-purpose destination with a brewery, a distillery, a restaurant, and an outdoor stage. Pro tip: get the to-die-for pulled pork nachos.

Brown County is one of those places where you can choose to go-go-go, or you can kick back and relax. Either way, it’s definitely worth the drive.

Learn more about Brown County and how it became the tourist destination it is today.

Where to stay in Brown County: Abe Martin Lodge is located within Brown County State Park. Bring the kids and your swimsuits; they’ve got an indoors water park. Want something more secluded? There are cabins, too.

CVB: Brown County, browncounty.com

Sandusky, Ohio

Driving time: 4 hours 45 minutes

Sandusky is most famous for being the home of Cedar Point amusement park, but this city on the shores of Lake Erie is much more than roller coasters and funnel cakes.

A fun way to get an overview is to take a Segway tour. Sandusky Segwave offers guided tours through the historic downtown. Perched atop your personal transporter, you’ll glide past historic sites, through city parks, along the lakefront, and past the Merry-Go-Round Museum. You’ll learn about the town’s very beginnings, as well as its role in the Underground Railroad.

Another reason to visit Sandusky is Kelleys Island. Take a high-speed ferry to the largest American island in Lake Erie for a day of art, shopping, and wine.

While you’re on the island, don’t miss Glacial Grooves State Memorial. This National Natural Landmark protects the largest easily accessible grooves in the world. To see them is to witness the power of the glaciers that shaped North America.

Before you go back to Sandusky, get a scoop of Lake Erie Cookie Island Monster. It’s the official ice cream of Ohio’s Lake Erie Shores and Islands , Sandusky’s visitors bureau.

Warning: it will turn your tongue blue!

Check out my guide to see many more things to do on Kelleys Island .

Where to stay in Sandusky, Ohio: Hotel Kilbourne . This place puts the boutique in boutique hotel. In addition to being the only Sandusky hotel that’s on the water, it’s also got a rooftop bar and an on-site restaurant.

CVB: Ohio’s Lake Erie Shores and Islands, shoresandislands.com

Driving time: 5 hours, or as long as you’d like!

Route 66 epitomizes the freedom of the open road, and it begins in Chicago. The route became official in 1926, providing many small towns access to significant national roadways for the first time. Although it was decertified in 1985, the Mother Road lives on.

This scenic byway changed course over the years, and these alignments are well marked in Illinois. If you’re short on time, I-55 will take you from one attraction to the next, but the fun of driving one of the country’s most historic byways is in following its original path.

Some of the most popular roadside attractions include Buckingham Fountain (not technically on Route 66, but you’re so close!), the Gemini Giant, Bunyon’s Statue, and Carlinville’s Million Dollar Courthouse.

Route 66 in Illinois is only 301 miles, but it’s nearly a century of Illinois history, so take your time.

More road trips from Chicago between 3 and 5 hours:

• Iowa City, Iowa; 3 hours 45 minutes
• Door County, Wisconsin ; 3 hours 50 minutes
• Bloomington, Indiana ; 4 hours
• Spencer, Indiana : 4 hours
• Collinsville, Illinois and Cahokia Mounds State Historic Site : 4 hours 45 minutes
• Traverse City, Michigan; 4 hours 55 minutes

Want an epic trip from Chicago but don’t feel like driving? Consider a train to Seattle – here’s what it’s really like to ride the Amtrak Empire Builder !

Map of Road Trips from Chicago

I hope these delightful road trips from Chicago will help you find someplace wonderful to visit for your weekend getaways. Each place is special and offers unique experiences. When you go, I’d love it if you’d share your photos in our Facebook group .

Oh, and be sure to bookmark this page, because I’ve got more destinations to add!

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The Best Road Trips from Chicago with Itineraries

Looking to get out and explore? There are so many unique places to visit that are just a car ride away! From quaint small towns to interesting cities to exciting outdoor adventure and everything in between, here are the best road trips from Chicago.

Afterward, you may also be interested in reading suggestions for

Fun Spring Break Trips from Chicago .

The Best Road Trips from Chicago

Starting with quick weekend getaways, this list is ordered by distance and ends with long road trips from Chicago.

HERITAGE TRAIL, INDIANA

This 90-mile scenic route will take you through northern Indiana's off-the-beaten-path towns where time slows down. The loop rambles through the communities of Goshen, Elkhart, Middlebury, Nappanee, Bristol, Wakarusa, and Shipshewana.

You'll discover winding country roads, talented artists, old-fashioned entertainment, recreational areas, blossoming gardens, and delicious treats.

From mid-May to mid-September, the trail coincides with the colorful Quilt Gardens project. 16 gigantic gardens and 23 painted murals embellish the trail with dazzling flowers in unique designs.

Drive Time: 2 hours to Elkhart Visitor Center

On the Way: University of Notre Dame, The Oliver Mansion, and Bonnie Doon Drive-In.

What to Do: Quilt Gardens, Wellfield Botanical Gardens, RV/MH Hall of Fame & Museum, Pumpkinvine Bike Trail, Ruthmere Mansion, Old Bag Factory, Linton's Enchanted Gardens, Bonneyville Mill County Park, and Menno-Hof.

Where to Eat & Drink: Rise N' Roll, Blue Gate Restaurant & Bakery, Iechyd Da Brewing, Das Dutchman Essenhaus, and Dutch Country Market.

Where to Stay: Excellent Hotel with a Great Location and Free Buffet Breakfast

SOUTH HAVEN, MICHIGAN

If you're looking for a relaxing destination with beach access, good restaurants, and a bike trail, South Haven is it. With its close proximity, southwest Michigan is amongst the top one day road trips from Chicago.

The walkable idyllic small town is right down the street from the Lake Michigan waterfront where you can see some of the best sunsets in the Midwest. There's plenty of opportunities to get out on the water: charter a fishing boat, take a sailing excursion or rent a jet ski.

If you'd like to do more than hit the beach then check out the Kal-Haven Trail, a former railroad route, that runs 33.5 miles from South Haven to Kalamazoo. It's a quiet and easy ride through blueberry fields, tree tunnels, and across a few bridges.

Drive Time: 2 hours, 15 minutes

On the Way: Four Winds Casino

What to Do: Kal-Haven Trail, DeGrandchamp Farms, Michigan Maritime Museum, Friends Good Will Tall Ship, and the Farmers Market.

Where to Eat & Drink: Golden Brown Bakery, Harbor Light Brewery, Chomp Gourmet Hot Dogs, Captain Nemo's, Phoenix Street Cafe, Idler Riverboat, Clementine's, and 12 Corners Vineyards.

Where to Stay: Historic Hotel in the Heart of Town walking distance to the Beach

GALENA, ILLINOIS

Galena is a must-experience destination in the Midwest especially if you live in Illinois. It is one of the unforgettable places to visit near Chicago with rolling hills, historic landmarks, and a super charming Main Street that will make you feel like you stepped into a Hallmark movie.

Start your visit at the historic Old Market House built in 1845 and now serves as Galena's Welcome Center. You'll learn about the fascinating history of the area and find information for your visit.

From springtime through fall, bike the River Trail, hike at Casper Bluff Preserve, or paddle the Galena River. The Alpine Slide, a 2,050-foot outdoor track, is a unique 2-minute adventure on the banks of the Mississippi River.

When the snow starts to fall, hit the slopes at Chestnut Mountain, one of the most popular ski destinations in the Midwest, or ice skate, sled or snowshoe at The Nordic Center at Eagle Ridge Resort.

While in town, hop on a trolley for a tour, visit wineries, and browse all the specialty and boutique shops.

Galena is on the Great River Road in Illinois along with some other special stops that make the scenic byway a unique Midwest road trip. Click on the link to read all about it!

Drive Time: 2 hours, 45 minutes

On the Way: Rafters Restaurant, Apple River Fort State Historic Site, Highway 20 Brewing Company, Horseshoe Mound Preserve, and Long Hollow Scenic Overlook.

What to Do: Galena Cellars Vineyard, Ulysses S. Grant Home, Galena Trolley Tour, and Grant Park

Where to Eat & Drink: Frank O'Dowd's Irish Pub & Grill, Durty Gurt's, The Log Cabin Steakhouse, Fried Green Tomatoes, Otto's Place, and Gobby's Sports Pub & Eatery.

Where to Stay: Cozy Hotel with an Indoor Pool & Spa and Cool Bar

PARKE COUNTY, INDIANA

Indiana has 98 historic covered bridges and Parke County is home to 31 of them. The central west area is also home to Indiana's largest festival, The Parke County Covered Bridge Festival, held every October in honor of the famous crossings.

Here, you'll also find quaint towns among rolling hills and two state parks to hike with deep gorges, wooden ladders, rocky hollows, and natural arches making the area one of the best fall road trips from Chicago.

Drive Time: 3 hours

On the Way: Kankakee Sands Bison Viewing

What to Do: Bridgeton Mill, Turkey Run State Park, Mansfield Roller Mill and Covered Bridge, Narrows Covered Bridge, Rockville Lake Park, Roseville Covered Bridge and downtown Rockville.

Where to Eat & Drink: Wheel House Donuts, Cross at Walk Winery, Thirty-Six Saloon, Big Berry, and Drunk Tank Winery.

Where to Stay: Cabin or Hotel Stay with an Indoor Pool

HAMILTON COUNTY, INDIANA

Under 200 miles away from Chicago and just 23 miles north of Indianapolis, Hamilton County is a fantastic option for a weekend getaway.

With lively communities bursting with arts and entertainment districts, outdoor activities, historic squares, boutique shopping, and diverse restaurants, Hamilton County deserves its own place on the list.

If you like to eat and drink, you can dedicate an entire weekend chasing giant pork tenderloins, local donut shops, and/or craft breweries. Make sure to spread your time evenly within the cities of Westfield, Carmel, Noblesville, and Fishers.

On the Way: Fair Oaks Farm, Cairo Skywatch Tower, Wildcreek Winery, and Jerry E. Botanic Gardens.

What to Do: Monon Bike Trail, Carmel Arts and Design District, Strawtown Koteewi Park, Hamilton County Courthouse & Old Sheriff's Residence and County Jail, Center of the Performing Arts,

Where to Eat & Drink: Urban Vines Winery and Brewery, Wolfies Grill, Rosie's Place, Cafe Patachou, Books & Brews, and Divvy Restaurant.

Where to Stay: Upscale Boutique Hotel in a Great Location

INDIANAPOLIS, INDIANA

Home to the state capitol, the world's oldest continuously operated racecourse, and the world's largest children's museum, Indianapolis has endless vacation potential.

Kick off your visit at Monument Circle, an impressive centerpiece circling the 284- foot tall Soldiers' and Sailors' Monument. The spectacular views from the observation deck will get you pumped to explore the city.

Once back on the ground, don't miss The Indianapolis Motor Speedway Museum, home of the Indy 500, for a chance to learn all about the history of racing, fast cars, and to see the track up close and personal.

For those looking for outdoor adventure, the Central Canal and White River State Park offer quiet respites from the bustling urban atmosphere with biking, pedal boat rentals, kayaking and segway tours.

If traveling with kids, spend an entire day at the gigantic Children's Museum of Indianapolis. Each exhibit will entertain the whole family.

What to Do: Indianapolis Motor Speedway, The Children's Museum, Monument Circle, Connor Prairie Interactive History Park, Canal Walk, Indiana State House, White River State Park, and Indianapolis Zoo.

Where to Eat & Drink: St. Joseph Brewery, Cafe Patachou, BRU Burger Bar, The Rathskeller, St. Elmo Steak House, and Slippery Noodle Inn.

Where to Stay: Hotel with Ideal Downtown Location & Indoor Swimming Pool

LAKE ERIE OHIO COASTAL TRAIL & CEDAR POINT

It's time to ditch Lake Michigan and discover another one of the Great Lakes. You can pick up the Lake Erie Ohio Coastal Trail in Toledo and follow the shoreline to Conneaut.

Along the 293-mile route, you'll discover the second-oldest operating amusement park in the United States (which happens to also be the best in the Midwest), old-time lighthouses, water parks an underrated cool city, swimming beaches, coastal towns, and beautiful state parks.

Being along the lake, there are numerous outdoor activities to choose from, plus historical and entertaining options on the drive. You'll have a newfound love and appreciation for Lake Erie after this sensational road trip.

Drive Time: 4 Hours to Toledo

On the Way: University of Notre Dame, Shipshewana, RV/MH Hall of Fame & Museum

What to Do: Marblehead Lighthouse State Park, Cedar Point Amusement Park, Rock n' Roll Hall of Fame, and Fairport Harbor Marine Museum and Lighthouse.

Where to Eat & Drink: Dock's Beach House Restaurant in Port Clinton, New Sandusky Fish Company, Mary's Kitchen in Geneva-on-the-Lake, Old Prague in Vermilion, Madsen Donuts in Geneva, and White Turkey Drive-in.

Where to Stay: Waterfront Property near Cedar Point

BLOOMINGTON, INDIANA

Bloomington tops the list of coolest college towns in the Midwest. There's always something going on between outdoor festivals, sports games, and music events.

Take a tour of one of the most beautiful campuses in the nation, go brewery hopping, or explore the area's natural beauty.

There's a reason Bloomington is referred to as the "Gateway to Scenic Southern Indiana," just twenty minutes away is the beautiful Lake Monroe and the Hoosier National Forest.

Drive Time: 4 hours

What to Do: Hickory Ridge Fire Tower, B-Line Trail, Indiana University Tour, and Tibetan Mongolian Buddhist Cultural Center.

Where to Eat & Drink: Nick's English Hut on Kirkwood, Laughing Planet Cafe, Oliver Winery, Crazy Horse, Cardinal Spirits, Upland Brewing Company, and Switchyard Brewing.

Where to Stay: Nice Hotel Walking Distance to University with Free Breakfast

HANNIBAL, MISSOURI

The river town of Hannibal is all about Mr. Samuel Clemens, aka Mark Twain. The prolific American writer grew up in this charming small town and many of his tales were inspired here.

Take a ride on the Mississippi, tour Twain's boyhood home and climb in the caves he played in and helped shape his imagination.

If you want to make your trip extra memorable, visit Memorial Day Weekend when the family-friendly Twain on Main Festival takes place featuring an arts and craft event, live music, Mark Twain performers, and a wine & beer garden with local favorites.

Drive Time: 4 1/2 hours

On the Way: Route 66 (see below for stops) to Springfield (Lincoln attractions)

What to Do: Mark Twain Boyhood Home & Museum, Mark Twain Cave, Lovers Leap, Mississippi Riverboat, Memorial Lighthouse, and Cave Hollow West Winery.

Where to Eat & Drink: Fiddlesticks Food & Spirits Company, Mark Twain Brewery, Becky's Old Fashioned Ice Cream Parlor and Emporium, Becky Thatcher's Diner.

Where to Stay: No-frills Chain with Indoor Pool and Free Breakfast

Unique and Romantic B&B with Breakfast and Full Bar

ROUTE 66: CHICAGO TO SPRINGFIELD, ILLINOIS

Route 66 is the most popular road in the United States and it begins in Chicago! For a fun weekend getaway, take a ride to the state capital of Illinois.

On the way, you'll find quirky roadside attractions along with interesting small towns. There are a ton of fun photo opportunities, colorful murals, and historical places along the route.

Once you arrive in Springfield, learn about one of America's most beloved presidents, Abe Lincoln, and see where he lived and worked.

Read here for a complete Springfield Itinerary to make the most of your time in the city.

Drive Time: 5 hours

On the Way: Old Joliet Prison, Gemini Giant, Launching Pad, Funks Grove Pure Maple Sirup, Route 66 Hall of Fame, World's Largest Covered Wagon, and Paul Bunyan Statue.

What to Do: Lincoln Home, Abraham Lincoln Presidential Museum, Lincoln Tomb, Ergadoozy Creative Play Center (kids under 12), Henson Robinson Zoo, Illinois State Capitol, and Knight’s Action Park.

Where to Eat & Drink: Cozy Dog Drive-In, Obed and Isaac's Brewery, Incredibly Delicious, Engrained Brewery & Restaurant, Mel-O-Cream Donuts, and Route 66 Motorheads.

Where to Stay: Downtown Hotel with Indoor Pool

ST. LOUIS, MISSOURI

Saint Louis has it all - good food, unique museums, craft breweries, and outdoor activities.

This Midwest destination is easy on the pocketbook too with most of the attractions and museums being free.

Don't miss the Gateway Arch; one of our newest national parks with a new state-of-the-art visitor center, the City Museum; the wackiest "museum" I've ever been to, and Anheuser Busch Brewery; a tour where you can also see the famous Clydesdales.

St. Louis is a great destination for couples, families, and solo travelers with an array of vacation activities to choose from.

On the Way: For a delightful lunch on the way down, stop halfway in Bloomington at Rosie's Pub. It's a popular restaurant serving up delicious sandwiches and burgers in one of the oldest buildings in town.

What to Do: St. Louis Zoo, The Arch, City Museum, Anheuser-Busch Brewery, Forest Park, Cathedral Basilica of St. Louis, Ballpark Village, and the Missouri Botanical Garden.

Where to Eat & Drink: Bogart's Barbecue, The Fountain on Locust, Crown Candy Kitchen, Hodak's Restaurant and Bar, Civil Life Brewery, and 360 rooftop bar.

Where to Stay: Well Reviewed Hotel near the Arch with a Free Hot Breakfast & Swimming Pool

CLEVELAND, OHIO

Cleveland provides an array of attractions from action-packed sporting events to interesting museums and even a few quirky stops like Ralphie's house in A Christmas Story.

Progressive Field, the Cleveland Indians' turf, is right near the pedestrian-friendly East 4th street which is the entertainment district downtown lined with restaurants and pubs. Down the street, take your chances with Lady Luck at a casino which also happens to be in the department store where the infamous 1983 Christmas movie was filmed.

And no visit to Cleveland would be complete without the Rock and Roll Hall of Fame experience . The museum launches visitors through the evolution of the shake-rattle-and-roll era that exploded in America.

And lastly, only 20 miles south is a national park to check off your list, Cuyahoga Valley. You can explore the park on a side trip from Cleveland or Akron.

Drive Time: 5 hours 20 minutes

On the Way: Cedar Point Amusement Park

What to Do: James A Garfield Memorial, Cleveland Botanical Garden, Cultural Gardens, Rock & Roll Hall of Fame, and A Christmas Story House.

Where to Eat & Drink: Collision Bend Brewery, West Side Market, Mabel's BBQ, Great Lakes Brewery, Lindey's Lake House, Alley Cat Oyster Bar, and Fat Cats.

Where to Stay: Reasonably priced 4-star hotel with indoor pool and lake views

SHAWNEE NATIONAL FOREST, ILLINOIS

You won't believe you're still in the Prairie State once you arrive in Shawnee National Forest. It is one of the best-kept secrets in Illinois.

It's a great destination to unplug and get back to nature. Start with the 1.7 mile Rim Rock Trail which will guide you through 300-year-old oak trees and narrow crevices to a beautiful canyon.

Explore the Cave-in-Rock overlooking the Ohio River, the historic cavern provided a safe haven for frontier outlaws back in the day. Take the Cave in Rock Ferry across the river to the small Amish village in Marion.

Don't miss a sunset at Garden of the Gods and a hike up Triggs Tower for more beautiful views.

What to Do: Rim Rock Recreation Trail, Burden Falls, Triggs Tower, Bell Smith Springs Recreation Area, Cave-in-Rock, Inspiration Point, and Garden of the Gods.

Where to Eat & Drink: The Diver Down, Garden of the Gods Outpost, E'Town River Restaurant, and Hogg Hollow Winery.

Where to Stay: A Beautiful Cabin with Private Bathroom and Deck

PATOKA LAKE, INDIANA

One of the best road trips from Chicago during Covid we took was to Patoka Lake. It is a destination that offers outdoor activities, that isn't very busy especially midweek, and where you can get out on a lovely lake.

Combine the trip with visiting the small towns of French Lick, known for its historic mineral springs, and Jasper, home to the Indiana Hall of Fame.

Make sure to rent a pontoon for a day on the lake and to take a walk through the stunning French Lick Resort and West Baden Springs Hotel for a glimpse into the past.

Drive Time: 5 1/2 hours

On the Way: Stop for lunch in a booming college town - either Lafayette or Bloomington.

What to Do: French Lick Casino, French Lick Scenic Railway, and Patoka Lake State Park.

Where to Eat & Drink: Patoka Lake Winery, 33 Brick Street, German Cafe, and French Licks Ice Cream.

Where to Stay: A 3-bedroom Country Cabin on the Lake

SANTA CLAUS, INDIANA

If you are looking for a fun wholesome summer trip for the family, head over to Santa Claus, Indiana.

With free soft drinks, free parking, free sunscreen, and free Wi-Fi, you can't go wrong with a visit to Holiday World and Splashin' Safari.

Home to the world's longest water coaster and America's only launched wing coaster, both amusement parks will keep the whole family entertained.

In between, make sure to track down all the festive spots that'll have you celebrating Christmas in July.

On the Way: Lincoln Boyhood National Memorial

What to Do: Holiday World Amusement Park, Splashin’ Safari Water Park, Lincoln State Park, Santa Claus Christmas Store, Santa’s Candy Castle, Santa’s Stables, Santa Claus Museum, and Holiday Drive-In.

Where to Eat & Drink: Frosty's Fun Center

Where to Stay: Santa's Lodge just not far from the Amusement Park

Rental RVs and Holiday Cabins

PUT-IN-BAY, OHIO

Where should I go for a weekend getaway from Chicago? Let me introduce you to South Bass Island in Ohio that is home to the small charming village of Put-in-Bay.

Even though there's plenty to do for families, this Midwest must-experience destination is best for couples or friend getaways. It's where golf carts roam and drinks flow with over 25 bars, breweries, and wineries.

From boating to paddle boarding, water activities are one of the best things to do when visiting. Along with catching a sunset at South Bass Island State Park, touring the wineries, and eating and drinking your way through town.

Drive Time: 5 1/2 Hours

On the Way: Shipshewana, Indiana's cutest Amish town.

What to Do: Observation Deck at Perry’s Victory and International Peace Memorial, island tour by tram, bike, or golf cart, Heineman’s Winery and Cave Tour, the monument view from Oak Point State Park, swimming at The Sand Bar, and the Massie Cliffside Preserve.

Where to Eat & Drink: Put-in-Bay Brewery, Chocolate Cafe & Museum, The Forge, Put-in-Bay Winery, Biergarten at the Boathouse, The Boardwalk, and Topsy Turvey's Bar & Grill.

Where to Stay: A Private Guesthouse with Free Bikes and a Fabulous Breakfast

AKRON, OHIO

Where can I go 6 hours from Chicago? Akron, Ohio that's where!

This is a city that surprised us in so many ways, not to mention, it's right next door to one of the few national parks in the Midwest.

Catch a minor league baseball game, tour an incredible historic mansion, chase waterfalls in Cuyahoga National Park, and visit an impressive art museum.

Drive Time: 6 hours

What to Do: Akron Art Museum, Cuyahoga Valley National Park, Akron Rubber Ducks, Stan Hywet Hall, and Akron Civic Theatre.

Where to Eat & Drink: The Peanut Shoppe, Mr. Zub's Deli & Bar, Lock 15 Brewing Company, and El Patron Tequileria & Cuisine.

Where to Stay: Modern Hotel with Lounge and Indoor Pool

TWIN CITIES, MINNESOTA

Saint Paul and Minneapolis, commonly called the Twin Cities, have a lot to offer for a vacation.

St. Paul is a little quieter with the state capitol and more daylife. While Minneapolis is where you go for art, theater, and nightlife. Both have a ton of breweries and great food options.

Discover the area through fun attractions like the Mall of America, the Science Museum of Minnesota, Como Zoo, Can Can Wonderland, and the Walker Art Sculpture Garden.

And do not miss the most beautiful places like the Cathedral of Saint Paul, the Minnesota State Capital, Como Conservatory, the historic homes of Summit Avenue, Lake Phalen, and Minnehaha Falls.

On the Way: Eau Claire, an Underrated Wisconsin Destination.

Where to Eat & Drink: Band Box, Summit Brewing Company, Keg and Case Market, Bad Weather Brewing, The Anchor Fish & Chips, and The Nook.

Where to Stay: Hotel with a Free Shuttle and Modern Rooms

CLEAR LAKE, IOWA

Clear Lake is a little hidden gem in the state of Iowa and it's another destination only 6 hours away from Chicago.

Cruise the Lady of the Lake, an authentic paddlewheel boat, while taking in the sights and learning some fun facts about the area.

Take in a show and tour The Surf Ballroom, where Buddy Holly, Ritchie Valens, and JP “The Big Bopper” Richardson played their last concert. Frozen in time, it'll transport you right back to 1959.

Eat, drink, and shop along Main Avenue, the hub of this friendly lakefront community.

And before you leave, drive north to Buddy Holly's Crash Site, you can't miss the giant Holly's iconic black eyeglasses.

On the Way: Galena's Helluva Half Mile Main Street

What to Do: Lady of the Lake Cruise, The Surf Ballroom & Museum, Clear Lake State Park, and Central Gardens of North Iowa.

Where to Eat & Drink: Cabin Coffee, Starboard Market, PM Park, South Shore Donuts, Lake Time Brewery, and Sevens Steak House.

Where to Stay: Adorable Rental with Free Bicycles walking distance to the Surf & Downtown

PORCUPINE MOUNTAIN STATE PARK, MICHIGAN

Michigan's Upper Peninsula is pleasant in the spring and summer, but it is also one of the best fall road trips from Chicago. And no trip there is complete without a visit to the Porcupine Mountains Wilderness State Park.

With 60,000 acres of old-growth forest, meandering rivers, jaw-dropping vistas, and flowing waterfalls, the “Porkies” will impress any traveler. It's kind of hard to believe you can find these views in the Midwest!

Drive Time: 6 hours 40 minutes

On the Way: Oshkosh, Wisconsin.

What to Do: Bond Falls, Lake of the Clouds, Escarpment Trail, Presque Isle Falls, Summit Peak Observation Tower, Big Carp River Trail, Union Spring Trail, and Porcupine Mountains Chairlift.

Where to Eat & Drink: White Pine's Yooper Diner, Antonio's Restaurant, and Hoop'n Holler Tavern.

Where to Stay: Chain Hotel only 15 minutes from the Park

RED RIVER GORGE, KENTUCKY

Listed on the National Register of Historic Places and a National Natural Landmark and National Archaeological District, Red River Gorge is a place that should not be overlooked as a road trip from Chicago.

Located in the Daniel Boone National Forest, there are over 100 natural sandstone archways, waterfalls, dense woodlands, exposed limestone ledges, tunnels, and bridges. 

Red River Gorge is an outdoor enthusiast's dream destination.

Drive Time: 7 hours

On the Way: Kentucky Horse Park in Lexington

What to Do: Nada Tunnel, Sheltowee Trace National Recreation Trail, Gladie Historic Site and Visitor Center, Sky Bridge Trail, Angel Windows Trail, Chimney Top Rock Trail, Cliff Trail, and Hidden Arch.

Where to Eat & Drink: Sky Bridge Station, Red River Rockhouse, Thatcher Barbecue Company, and Miguels Pizza.

Where to Stay: Great Resort surrounded by Natural Beauty

KANSAS CITY, MISSOURI

We are moving onto longer drive times so anything below here are my recommended best road trips from Chicago for a week or more.

Kansas City has culturally rich areas, bold and modern architecture mixed with distinguished historic buildings, a flourishing arts scene, and finger-licking-good barbecue.

If that doesn't convince you, it is also home to the best World War I Museum in the country and a highly rated art museum admired by all that visit.

Drive Time: 7 hours 45 min

On the Way: Springfield, Illinois.

What to Do: Crossroads Art District, National World War I Museum, Nelson-Atkins Museum of Art, City Market, Rose Garden at Loose Park, and Country Club Plaza.

Where to Eat & Drink: Arthur Bryant's, Cinder Block Brewing Company, Gillis Cafe and Hangout, Pigwich, Joe's Kansas City Bar-B-Que, and Boulevard Brewing Company.

Where to Stay: Hotel with Ideal Location and Free Breakfast

BRANSON, MISSOURI

Branson is probably one of the most underrated road trips from Chicago for families.

It's not just cheesy musicals and religious shows, there's a lot of natural beauty, fun attractions, and cool things to do for kids and adults alike. 

Drive Time: 8 hours

On the Way: St Louis and the quirky stop of Uranus.

What to Do: Titanic Museum, Silver Dollar City Amusement Park, Table Rock Lake Trail, Dick’s 5 & 10 Store, Top of the Rock, Shepherd of the Hills Fish Hatchery, and Branson Landing.

Where to Eat & Drink: Danna’s BBQ & Burger Shop, White River Fish House, Andy’s Frozen Custard, The Paddlewheel, Clockers Cafe, and Mel's Hard Luck Diner.

Where to Stay: Modern Hotel on the Branson Landing

FINGER LAKES, NEW YORK

If you are interested in 10 hour road trips from Chicago, Finger Lakes is the place to go especially if you enjoy hiking, lakes, and drinking.

The region is renowned for its wine trail but it also has more than 75 craft breweries! Don't miss the wonderful state parks and the interesting towns of Hammondsport and Corning.

Drive Time: 10 1/2 hours

On the Way: Rock n Roll Hall of Fame in Cleveland.

What to Do: Watkins Glen State Park, Corning Glass Museum, Hammondsport, Robert H. Treman State Park, and Mark Twain's Study and Burial Site.

Where to Eat & Drink: Market Street Brewing Company and Restaurant, Glenora Wine Cellars, Rooster Fish Brewing Tasting Room, Nickel's Pit BBQ, and Wagner Vineyards Estate Winery.

Where to Stay: Inn with a Beautiful Grounds & a Free Breakfast

BLACK HILLS, SOUTH DAKOTA

If you're planning a 2 week road trip from Chicago, head to the beautiful Black Hills of South Dakota.

You'll find scenic drives, history, wildlife, and natural beauty throughout the entire region. And, some goofy roadside attractions on the way!

Drive Time: 14 hours

On the Way: Austin, Minnesota

What to Do: Wildlife Loop in Custer State Park, Mount Rushmore, Wind Cave National Park, Evans Plunge Hot Springs, Crazy Horse Memorial, and Badlands National Park.

Where to Eat & Drink: Chuck Wagon Dinner Show, Baker’s Bakery & Cafe, Black Hills Burger & Bun Co, Wall Drug, and Legion Lake Lodge. 

Where to Stay: Bavarian Inn with an Outdoor Pool

THEODORE ROOSEVELT NATIONAL PARK, NORTH DAKOTA

If you like cool roadside attractions, quirky vibes, outdoor adventure, and getting off the beaten path then this is one of the best long road trips from Chicago.

Don't put off North Dakota as your last state because it has a lot going for it. The Theodore Roosevelt National Park has sprawling natural beauty with winding waterways and painted canyons along with free-roaming bison and wild horses.

The neighboring town of Medora is one of my favorite small towns in the U.S. with an authentic Western energy. Visit the Cowboy Hall of Fame to learn about cowboy culture, catch a show at the famous Medora Musical, an outdoor extravaganza with the real badlands as its backdrop, and stroll the streets of this tiny charming town.

On the Way: Fargo-Moorhead Visitors Center, Fargo Air Museum, Frontier Village, World's Largest Buffalo, Lewis and Clark Riverboat, Fort Abraham Lincoln State Park, North Dakota Heritage Center and State Museum, North Dakota State Capitol, and the Enchanted Highway.

What to Do: The Medora Musical, Chateau de Mores State Historic Site, Pitchfork Steak Fondue, ND Cowboy Hall of Fame, South Unit 36-mile Loop Drive, Sunset at Wind Canyon, Painted Canyon Visitor Center Overlook, Ridgeline Nature Trail, Roosevelt’s Maltese Cross Ranch Cabin, Boicourt Trail, Buck Hill Trail, Oxbow Overlook, River Bend Overlook, Cannonball Concretions Pullout, and 14-mile North Unit Scenic Byway at the Theodore Roosevelt National Park.

Where to Eat & Drink: Sandy's Donuts, Drekker Brewery, Tower Travel Center, Little Missouri Saloon & Dining Room, Medora Uncork'd, and Hidden Springs Java.

Where to Stay: Ranch Cabin in the Heart of Medora

Hotel with Free Breakfast and Indoor Pool

One of the most beautiful Midwest states is just a short drive from Chicago, here are fun day trips in Michigan to help you plan. 

I hope you enjoyed my favorite road trips from Chicago 2021 edition! If you have any other recommendations, please let us know in the comments below!

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Angela E. is a travel writer from the Chicagoland area who has visited all 50 states in the US and has traveled extensively around the world. She is passionate about exploring the great outdoors and hiking in particular. Her love for nature has taken her to some of the most beautiful locations on the planet. She has written extensively about her travels on her own website, Dang Travelers, and has been published in collaboration with other travel websites and multiple visitor bureaus around the country.

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10 Easy Weekend Getaways from Chicago—No Flights Required

Escape chicago for a few days with one of these 10, drivable weekend getaways and short road trips starting in chicago..

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Door County, Wisconsin, is one of the many easy-to-reach day trip destinations from Chicago.

Photo by Bailey Berg

Despite cries about that winter weather, Chicago is inarguably blessed with a little something we like to call location, location, location : With prime real estate on Lake Michigan, the Midwest city is about as far by car from Minneapolis (six hours) as it is Toronto (eight hours) and Nashville (seven hours). In this sense, it’s an ideal jumping-off point for a drivable trip. There are several weekend getaways from Chicago, whether you want to put some serious miles on your car or be somewhere new by the time your kids are done watching Cars. Read on for ten easy weekend getaway ideas from Chicago.

What cities are under three hours from Chicago by car?

• Milwaukee, Wisconsin (1 hour, 30 minutes)
• Madison, Wisconsin (2 hours, 25 minutes)
• Grand Rapids, Michigan (2 hours, 47 minutes)
• Peoria, Illinois (2 hours, 41 minutes)
• South Bend, Indiana (1 hour, 39 minutes)
• Indianapolis, Indiana (2 hours, 56 minutes)

The Dane County Farmers’ Market in Madison is one of the largest in the U.S.

Photo by MarynaG/Shutterstock

Geneva, Illinois

• Distance: An hour by car
• Best for: Singular art and great shopping

OK, OK. Geneva is technically a suburb of Chicago, but it feels worlds away, thanks to its small-town charm. Drop your bags at the boutique Herrington Inn & Spa , located on the Fox River, and set out to explore the city’s walkable downtown on foot. Public art abounds here, as do independent shops and restaurants (all told, there are more than 150 of them in the historic district).

Michigan City is a breath of fresh air not far away.

Photo by Andy Konieczny / Shutterstock

Michigan City, Indiana

• Distance: An hour and a quarter by car
• Best for: Hiking (and swimming for the brave)

On a clear day from Michigan City, you can see Chicago’s skyline across the water. Enjoy towering sand dunes, the cool waters of Lake Michigan, and nearly 50 miles of trails at Indiana Dunes National Park ; in Michigan City proper, attractions include the 19th-century Barker Mansion —listed on the National Register of Historic Places—and family-friendly Washington Park Zoo .

A lighthouse in New Buffalo, Michigan

Photo by Suzanne Tucker/Shutterstock

Harbor Country, Michigan

• Best for: A beach and wine combo trip

Comprising the eight towns of Michiana, Grand Beach, New Buffalo, Three Oaks, Union Pier, Lakeside, Harbert, and Sawyer, Harbor Country is a favored weekend escape from the Windy City, thanks to its beach and country offerings. There are also a number of world-class wineries and breweries in the area, including the popular Lehman’s Farmhouse and Dablon Vineyards and Winery , in nearby Baroda.

Milwaukee is home to one of the largest German populations in the U.S.

Photo by Jayne Lipkovich / Shutterstock

Milwaukee, Wisconsin

• Distance: An hour and a half by car
• Best for: Brats and brews

Milwaukee has a rich German heritage, which means the city is full of places to get a good beer and brat (and more beer, if that’s your thing). Both Pabst Blue Ribbon and Miller are based here, but don’t sleep on the smaller guys, including Milwaukee Brewing and Lakefront .

Mary stands atop the Golden Dome of the University of Notre Dame Main Administration Building.

Photo by Jonathan Weiss/Shutterstock

South Bend, Indiana

• Distance: An hour and forty minutes by car
• Best for: Whitewater rafting

There’s more to South Bend than Fighting Irish football, though we absolutely cosign the idea of a walk around Notre Dame’s scenic campus. Hit the rapids on East Race Waterway , North America’s first artificial white-water course, which cuts through the city, or visit the historic Robinson’s department store to throw your own pottery at the Pigeon and the Hen . Play arcade games—for free!—at the Garage Arcade and Bar , which has all the classics, Galaga and Ms. Pac-Man included.

The Fredrick Meijer Gardens spans 158 acres and features a host of outdoor art exhibits.

Photo by SNEHIT PHOTO / Shutterstock

Grand Rapids, Michigan

• Distance: Around three hours by car
• Best for: Beer, of course, but also outdoor sculptures

Voted “Beer City USA” in several national polls, Grand Rapids is known for its suds: Check out the Beer City Ale Trail , a map showcasing all of the options in the city. For food, we’re partial to strolling Downtown Market , which counts more than 20 vendors in the hall south of Heartside Park (a perfect picnic location, if you ask us). For an outdoor experience that requires a bit more activity, head to the 158-acre Frederik Meijer Gardens & Sculpture Park : here, you’ll find art by Auguste Rodin as well as a hall dedicated solely to carnivorous plants.

A dinosaur breaks out of the Children’s Museum in Indianapolis.

Photo by James Kirkikis/Shutterstock

Indianapolis, Indiana

• Distance: Three hours by car
• Best for: Museums, both traditional and quirky

Indianapolis is an incredible museum city. Although two of its most popular attractions are the Children’s Museum and the sprawling indoor-outdoor Indianapolis Museum of Art , don’t miss some of the city’s quirkier options: the Indiana Medical History Museum (not for the faint of heart) and the Kurt Vonnegut Museum and Library . Visit Indy’s famed City Market to sample more than 25 locally owned eateries; when you’ve had your fill, descend underground on a public catacombs tour, which takes place on the select Saturdays, May through October, between 10 a.m. and 3.15 p.m. (Private tours can be booked with Indiana Landmarks .)

Ann Arbor is known for its university, but a host of delights awaits all visitors.

Photo by Dark Vader / Shutterstock

Ann Arbor, Michigan

• Distance: Around three hours and 45 minutes by car
• Best for: Adventures on the river

Activities for all seasons abound in Ann Arbor, best known as the home of the University of Michigan. Tube, kayak, SUP, or canoe down the peaceful stretch of the Huron River—accessed from the 69-acre Gallup Park—or stroll U of M’s famed Matthaei Botanical Gardens and Nichols Arboretum . Be sure to make time for the city’s Kerrytown Market and Shops , a picturesque neighborhood full of independent boutiques and restaurants. ( Zingerman’s Deli , one of the best spots in Ann Arbor for a sandwich, is here.)

An aerial view of Door County, Wisconsin

Photo by Matt Sampson Photography/Shutterstock

Door County, Wisconsin

• Distance: Four and a half hours by car
• Best for: Exploring rugged coastline

A 70-mile-long peninsula, Door County is often called the “ Cape Cod of the Midwest” —and rightfully so. Just 50 miles northeast of Green Bay, Door County has stunning coves, cherry orchards, harbors, lighthouses, wineries, and some 300 miles of coastline. Newport State Park is an International Dark Sky Reserve , and the 900-acre Rock Island State Park has no cars; for a dose of small-town charm, stop by Ephraim, a Scandinavian-style village .

Traverse City might be a bit further away, but it’s worth the drive—especially in the fall.

Photo by Gary R Ennis Photos / Shutterstock

Traverse City, Michigan

• Distance: Five hours by car
• Best for: Exploring shops and galleries in a justifiably popular small town

No wonder Traverse City was named one of the sweetest small towns to visit in summer : a lakeshore beauty with art deco architecture, the city is beloved by many Chicagoans (including Oprah herself). One of Traverse City proper’s most popular attractions is the Village at Grand Traverse Commons: a hospital complex from the 19th century, the historic venue has since been reborn into a mixed-use space, with shops, restaurants, footpaths, and art galleries. Northwest of Traverse City is Leelanau Peninsula, which is home to the striking Sleeping Bear Dunes National Lakeshore .

Where can I go by train from Chicago?

No car? No problem. You can get virtually anywhere from Chicago by train: Memphis is 10 hours by rail; Seattle is 46. But for a weekend getaway, we’re partial to these picks:

• Indiana Dunes National Park (the South Shore Line from Chicago’s Millennium Station stops at four stations in the park )
• Milwaukee, Wisconsin (about 90 minutes by Amtrak from Chicago’s Union Station)
• Kalamazoo, Michigan (about two hours by Amtrak from Chicago’s Union Station)
• Grand Rapids, Michigan (about four hours by Amtrak from Chicago’s Union Station)

Of course, there’s plenty to do in Chicago itself before you head off; it was ranked number 2 in the best cities in the U.S. for 2023 , after all, thanks to its top restaurants , world-class museums, and abundant hotel options. On the other hand, if you’re feeling really adventurous, you could always take the ultimate epic road trip: 2,448 miles all the way to Santa Monica , California.

Happy weekending.

This article originally appeared online in 2020; it was most recently updated on August 31, 2023, to include current information.

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10 Best Weekend Road Trips From Chicago, Illinois

Posted by Brittany Varano June 01, 2021 Updated February 22, 2023

Sometimes you need a change of scenery, and these weekend road trips from Chicago make it easy to get away from the bustle of the Windy City.

Perfectly perched within reach to four different states, Chicago conveniently sits at the crossroads to destinations in Wisconsin, Michigan, Indiana, Iowa, as well as the rest of Illinois.

Its prime location means endless weekend road trips that range from city escapes to small-town excursions and outdoor getaways. And you’ll have your choice of several sandy beach towns lining the shores of neighboring Lake Michigan.

Below, you’ll find a diverse list of the best weekend road trips from Chicago to inspire your next adventure out of the city.

Related Read: The 10 Best Illinois Glamping Rentals

1. Milwaukee, Wisconsin

Milwaukee is an easy weekend trip just north of Chicago over the Wisconsin border. Known for its craft breweries and local eats, there’s a lot to do and see in this smaller midwestern city. If you’re interested in learning about the local history, make time to visit Milwaukee’s beloved museums like the historic art museum or the Harley Davidson Museum to marvel at one of Elvis Presley’s classic motorcycles.

If you’re a sports fan, make time to catch a Milwaukee Bucks basketball game or tailgate outside of Miller Park before watching the Brewers play ball. The end of summer is also a fantastic time to visit Milwaukee as Summerfest is in full swing. Summerfest is a music festival held along the picturesque shores of Lake Michigan in downtown Milwaukee and brings notable acts each year.

Distance from Chicago: 93 miles (approx. 1 hour and 30 minutes)

Related Read: 11 Best Cabin Rentals in Illinois For an Outdoor Getaway

2. Starved Rock State Park

If peace in nature is what you’re seeking, Illinois’ Starved Rock State Park is a beautiful outdoor getaway known for scenic sandstone canyons, numerous waterfalls, and miles of hiking trails. The park’s top sights include Lover’s Leap Overlook (a lookout point offering clear views of the Starved Rock Dam) as well as the Wildcat, French, and St. Louis canyons.

Summertime is the best time to visit, bringing sunshine and warm weather. Winter is also not a bad time to visit, when the canyon falls freeze over in a spectacular show of ice and snow. Many visitors opt to camp out in the state campground, where reservations can be made up to six months in advance. The park is on the Illinois River southwest of Chicago.

Distance from Chicago: 94 miles (approx. 1 hour and 30 minutes)

Related Read:   9 Fabulously Unique Places to Stay in Illinois

3. Indianapolis, Indiana

Indianapolis is an excellent weekend road trip from Chicago for city dwellers and racing fans. Home to the world-famous Indy 500 and the Indianapolis Motor Speedway Museum , car lovers can cheer on their favorite drivers and learn a bit about the sport’s history.

No visit to Indy is complete without sampling some local cuisine, including local specialities like pork tenderloin sandwiches and shrimp cocktail. The city was named as an ‘Underrated Food City in America’ by Condé Nast Traveler for its rich and diverse restaurants and dishes. Other popular things to do in Indianapolis include walking the eight-mile Indianapolis Cultural Trail that stretches through downtown or visiting the iconic Monument Circle.

Distance from Chicago: 184 miles (approx. 3 hours)

Related Read:   10 Romantic Getaways Near Chicago, Illinois

4. Galena, Illinois

For a taste of small-town living, look to Galena, Illinois . The city has consistently been ranked as one of America’s most livable cities and offers a lovely weekend trip from the big city. Galena is known for its quaint main street lined with historic brick buildings dating to the 1800s.

Visitors can tour the former home of Ulysses S. Grant and visit the beautiful grounds of the Dowling House, the oldest home in the city. Rolling hills and Native American effigy mounds surround Galena, such as the Horseshoe Mound, a nature preserve boasting views of three nearby states. The best way to experience Galena is to stay in a charming bed and breakfast or a local vacation rental.

Distance from Chicago: 164 miles (approx. 2 hours and 45 minutes)

5. Indiana Dunes National Park

Boasting the shortest distance of all the road trips from Chicago, the Indiana Dunes National Park is a convenient road trip from Chicago to northwestern Indiana. The park protects over 15,000 acres of diverse landscapes that include sunny beaches, sand dunes, wetlands, and forests.

The park is a four-season destination offering wildflowers in the spring, water fun in the summer, fiery colors as the leave change in the fall (and sunsets are great), and cross-country skiing in the winter.

Most people opt to camp out in the national park campground or stay in nearby vacation rentals. Besides the outdoor adventures inside the park, make time to shop at the Saturday European Market in Chesterton, visit the Old Lighthouse Museum , and indulge in Indiana comfort food.

Distance from Chicago: 49 miles (approx. 56 minutes)

6. Grand Rapids, Michigan

Get a feel for Michigan city life with a weekend in Grand Rapids . About three hours north of Chicago, the city was once a hub for furniture manufacturing, securing the nickname “Furniture City.” Today, locals and visitors alike enjoy strolling the downtown riverwalk along the Grand River, eating out at hip restaurants like Divani and Stella’s Lounge,  and shopping at the Grand Rapids Downtown Market.

The Frederik Meijer Gardens & Sculpture Park is another must-see stop, with walking trails meandering through nearly 160 acres of colorful gardens and sculptures. In the evening, sip cocktails as the sun sets at the New Hotel Marten’s hip rooftop.

Distance from Chicago: 177 miles (approx. 3 hours)

7. Madison, Wisconsin

Home to the majestic Wisconsin state capitol building, Madison is a charming city best known for its location on an isthmus surrounded by four scenic lakes. The University of Wisconsin Madison campus sprawls through the downtown area, bringing with it a vibrant artistic atmosphere as well as hip bars and restaurants. Along the pedestrian friendly State Street, boutique shops and charming cafes lead the way to the capitol building.

One of the best things to do in Madison includes visiting the Saturday farmers market, where 150 vendors line the capital square selling locally sourced produce, flowers, and sweet treats. Grabbing a pitcher of beer at the Union Terrace along Lake Mendota and visiting the admission-free Henry Vilas Zoo are also popular things to do. That said, Madison is a very outdoorsy city, so you’ll find plenty of options for everything from paddling to hiking, biking, and outdoor movies and festivals.

Distance from Chicago: 147 miles (approx. 2 hours and 20 minutes)

8. Lake Geneva, Wisconsin

Lake Geneva is a four-season resort destination in south-central Wisconsin. The city is named after the large 5400-acre Geneva Lake that attracts fishing and boating enthusiasts. The city’s Big Foot Beach State Park is one of the best places to go for swimming, sun tanning, and kayaking. If you enjoy casual walks, take a stroll along the Geneva Lake Shore Path that circles the lake for 21 miles.

While summer is an ideal time to make the most of the lake and surrounding beaches, winter also offers a unique weekend getaway. Every year, the Geneva National Resort and Club hosts the award-winning Ice Castles festival, where ice sculptures and structures amaze winter visitors. Prices and hotels cross into a variety of budget and lux options, but in general, it’s one of the cheaper towns for a summer getaway near Chicago.

Distance from Chicago: 83 miles (approx. 1 hour and 30 minutes)

Related Read:   13 Exciting Things to Do in Lake Geneva, Wisconsin

9. Saugatuck, Michigan

Saugatuck, Michigan , is an artsy beach destination best enjoyed in the summer. This small town is on Lake Michigan and Kalamazoo Lake, offering fantastic water fun like fishing, swimming, and boating. The area is also famous for its idyllic grassy dunes, Mount Baldhead Park hiking, river cruises, and the Dutch windmills and gardens in nearby Holland, MI.

The city’s center features Butler Street, where visitors can enjoy up-and-coming gourmet restaurants and boutique shops. Don’t forget to pack your swimsuit for a trip to Oval Beach. For the best experience, opt for a cozy B&B along the water or in the downtown area, but be sure to plan ahead as lodging fills fast in the summer.

Distance from Chicago: 141 miles (approx. 2 hours and 15 minutes)

10. The Wisconsin Dells

Known as the waterpark capital of the world, the Wisconsin Dells is a resort town with 20 different indoor and outdoor water parks and resorts. It’s a perfect weekend road trio from Chicago for families looking for something fun but family-friendly – and the area offers more to do than just waterparks. Take a tour along the Wisconsin River and surrounding forests on a Wisconsin Duck, an amphibious truck that dates back to WWII.

Be sure to check out other popular activities such as local winery tours, the hiking trails through nearby Devil’s Lake State Park, and the vibrant nightlife of downtown. When visiting, there are plenty of cozy Wisconsin Dells cabins to stay at if resort living isn’t for you.

Distance from Chicago: 195 miles (approx. 3 hours)

Explore More in the Midwest

12 of the Best & Most Unique Airbnbs in Illinois

10 Best Lake Camping Destinations in Wisconsin

Michigan National Park Guide: Everything You Need to Know

11 Peacefully Secluded Cabin Rentals in Wisconsin

10 Awesome Glamping Getaways in Michigan

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Seen in: Illinois , Midwest , Road Trips

Posted by Brittany Varano

Brittany is a freelance travel writer and avid photographer with a love of hiking and nature. Originally from Wisconsin, she fell in love with travel blogging after living and teaching English in South Korea. She’s now location independent and enjoys slow travel to new and exciting places.

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The 23 most unique day trips from Chicago

Break the mold with these under-the-radar, kitschy or otherwise unique trips within a few hours' drive of Chicago.

When it comes to a much needed escape from the city, there are countless day trips from Chicago if time doesn’t allow for a full weekend getaway . And luckily for the adventurous and curious, there are plenty of opportunities to swap typical activities like kicking back with brews for hiking  among bison or spelunking in an ancient cave. Many sites and experiences within driving distance of Chicago take you far beyond the norm, from year-round Christmas at an amusement park to (not so similar) replicas of some of the world’s most celebrated cultural sites. Midwesterners may love their weekend lake house tradition, but they also love the wacky, meaningful and unexpected. Here are the most unique day trips from Chicago.

RECOMMENDED: The best lakefront Airbnbs near Chicago

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The most unique day trips from Chicago

1.  Explore the country’s largest magic museum

Driving time from Chicago: About three hours

You'll find everything from obscure conjuring tomes to equipment used in Harry Houdini's most famous escape acts at the American Museum of Magic in Marshall, Michigan, home to the biggest collection of magic ephemera in the United States. With more than 350,000 artifacts onsite, there's more than enough magical entertainment to fill an afternoon: Take a self-guided tour through magic history, try to squeeze into a replica of Houdini's Milk Can Escape or book an appointment at the museum's Lund Memorial Library to pore over archival materials.

2.  Spot bison at Midewin National Tallgrass Prairie

Driving time from Chicago: About one hour

Want to get a firsthand look at why Illinois is nicknamed the Prairie State? Take a trip southwest of the city to Will County, where a herd of bison roam the 9,000-acre expanses of the Midewin National Tallgrass Prairie as part of an ongoing habitat restoration project (the area once housed the Joliet Army Ammunition Plant and bunkers still remain). Spotting the herd isn't a sure thing—it's a massive park, after all—so you're best off bringing a pair of binoculars and starting at the Iron Bridge Trailhead, which puts you closest to the bison pasture area. From there, a three-mile round trip hike will lead you to an overlook point outfitted with viewing scopes and benches to rest on.

3.  Go spelunking inside Cave of the Mounds

Wander among soda straws, flowstones, helictites and other stunning geological formations inside of Cave of the Mounds, a natural limestone cave near Blue Mounds, Wisconsin. Once home to a limestone quarry, the cave is now open for guided (or self-guided) tours through mineral deposits in shades of white, reddish brown, black, purple and gray. Fun fact: Whether you're visiting on a hot summer day or during the frigid depths of winter, the subterranean expanse is always a cool 50 degrees, so be sure to dress accordingly.

4.  See the Batmobile (and tons of other famous cars) at the Volo Auto Museum

Driving time from Chicago:  About an hour and a half

Don't think that you're a car person? A visit to the Volo Auto Museum just might change your mind. Throughout this suburban attraction's 33 exhibits, you can ogle everything from '50s-era Thunderbirds and Oldsmobiles (Vintage Cars), to Britney Spears' 2006 Mercedes-Benz and Elvis Presley's 1974 Cadillac (Cars of the Rich and Famous), to Scooby Doo's Mystery Machine and the Subaru driven by Paul Walker in Fast & Furious 7 (TV and Movie Cars). There's even an entire exhibition dedicated to different iterations of the Batmobile. Plus, if you're really hoping to find some artifacts that aren't car-related, check out the museum's collection of planes, antique card games, animatronics and music machines, or shop for new home decor at the nearby Volo Antique Malls.

5.  Tour modernist architecture in Columbus, IN

Driving time from Chicago: About four hours

Thanks to a highly successful funding program in the mid-20th century, the small-ish town of Columbus, Indiana is home to some of the Midwest's most stunning examples of Modern buildings, structures and public art, with works by Eero Saarinen, I.M. Pei, Richard Meier and other architectural luminaries dotting its downtown thoroughfares. You can pay for a guide to lead you through the highlights, but the town also offers a free audio tour app that leads listeners through 18 of the most prominent buildings in the area.

6.  Paddle along the African American Heritage Water Trail

Driving time from Chicago: About 40 minutes 

Chicagoans who love active, experiential learning can take an impactful day trip of paddling through history along the Little Calumet River, a waterway which, along with others, connects Lake Michigan with the Mississippi River. In a span of just seven miles, experience nearly two centuries of African American history, from the underground railroad and civil rights to the birth of environmental justice. Beginners can join an organized group paddle during the summer season while experienced water recreationists can follow a self-guided paddle outlined on the Openlands website .

7.  Hike around the iconic Farnsworth House

Driving time from Chicago: About an hour and a half

Located in Plano, Illinois at the banks of the Fox River, the glass-walled Farnsworth House—designed by Bauhaus architect Ludwig Mies van der Rohe as a weekend retreat for Dr. Edith Farnsworth—is both a National Historic Landmark and one of the area's foremost examples of Modernist architecture. Though the house has been besieged by floods throughout its 70-year history, ongoing preservation efforts have kept it in tip-top condition. Book a docent-led tour through the building (the summertime moonlight tours, which commence at dusk and loop around a lighted exterior path, are an especially beautiful option) and take some time to soak in the natural beauty of the home's 60-acre wooded grounds.

8.  Check out Amish Country in Shipshewana, IN

Driving time from Chicago: About two and a half hours

Escape the bustle of city life among the placid streets of Shipshewana, a teeny town nestled in the center of northern Indiana's Amish Country. Kick off your day with a tour of Menno-Hof—a museum dedicated to Amish and Mennonite history—or book a sight-seeing expedition aboard a horse and buggy, then fuel up with traditional Amish eats at family-style restaurants like A Taste of of Shipshewana (where you'll also find live cooking and quilting demonstrations). In the market for antiques and tchotchkes? Plan a visit on Tuesdays or Wednesdays from May through September, when the town hosts the Midwest's largest flea market.

9.  Explore the Bahá'í Temple

Driving time from Chicago: Around 30 minutes

No doubt you’ve seen pictures or driven by the striking Baha’i House of Worship in Wilmette, but make a day of it and actually witness the interior details. The temple of the Baha’i faith was built in 1953 after 50 years of planning and construction. It is currently open to the public daily with free admission to the temple’s domed auditorium and surrounding gardens. 

10.  Wander through a Tudor-style castle in Oregon, IL

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Driving time from Chicago:  About two hours

Back in the late 1920s, Chicago Daily News publisher and owner Walter A. Strong began construction on a Tudor-style manor to serve as his family's summer home. The end result—a 10-bedroom, 8-bathroom behemoth with a couple of secret passages to boot—can be explored in the present day through an hour-long tour, which covers the history of the Strong family, the castle's architecture and a brief history of medieval life. If you're got time after the tour, head to the nearby Castle Rock State Park (unaffiliated with the aforementioned castle, in case you were wondering) to hike among gorgeous sandstone bluffs.

11.  See the Great Pyramids without leaving Illinois

Driving time from Chicago: About one hour and five minutes 

One of the most unexpected I-94 sights is the Gold Pyramid House, a 1970s-era family compound featuring replicas of the Great Pyramid of Giza, a 55-foot statue of Ramses II and King Tutankhamun’s tomb. Full of objects and decor leaning from kitschy to cult-like, visitors can meander the grounds and attend events, and even take home Gold Pyramid Water and Gold Pyramid Vodka as souvenirs, though it’s unclear whether either were on sale in ancient Egypt. House tours on select Saturdays and by appointment only. 

12.  Meander through an English-style village next to the largest inland oil refinery

Driving time from Chicago: About 35 minutes 

Marktown Historic District may not be one of the seven wonders of the world, but it's certainly a marvel of Northwest Indiana. Built in 1917 as a planned worker community by renowned architect Howard Van Doren Shaw—10 years after the last home was sold in nearby planned community Pullman—Marktown became famous after its appearance in Ripley's Believe It or Not! for being  the only town in North America where cars park on the sidewalk and neighbors walk on the streets. Today, the quaint Tudor revival-style homes with bright colors and cheerful window boxes are in eerie contrast to the surrounding heavy industry. Learn about architecture and the area’s history in steel on a self-guided tour.  Then, refuel at Hegewisch favorite Pudgy’s Pizza before heading home.

13.  Ride a vintage train at the Illinois Railway Museum

The country's largest railway museum sits just outside the Chicago metropolitan area in Union, Illinois, where you can check out a massive collection of antique train cars and hop aboard working streetcars, steam and diesel trains that loop around the 100-acre campus. Plan for an entire day of exploration: The museum's buildings house all kinds public transportation artifacts, including an 1859 horse-drawn streetcar, every kind of CTA 'L' car and a display of working railroad signs and signals.

14.  Take a nature walk through Cantigny Park

Driving time from Chicago: About 45 minutes

This verdant Wheaton park—formerly the estate of the publishers of the Chicago Tribune— offers 29 acres of gardens and 160,000 plants, complete with two and a half miles of nature paths perfect for a leisurely afternoon stroll among the flowers. Military history buffs will also want to check out the First Division Museum on the park's grounds, which chronicles U.S. military history from World War I to the present.

15.  Find your zen in the Anderson Japanese Gardens

Driving time from Chicago: About two hours

Once you've thoroughly explored the lovely Garden of the Phoenix in Jackson Park, set your sights on a visit to the Anderson Japanese Gardens in Rockford. Designed by landscape architect Hoichi Kurisu, the 12-acre gardens feature trails, waterfalls, tranquil ponds, gravel gardens and an abundance of Japanese maples, among other plant life. Plan ahead and book the "Frank Lloyd Wright Meets 16th Century Japan Tour" that guides visitors through the garden's 16th century Sukiya-style tea house and the Laurent House, which has the distinction of being the only home Wright designed for a client with a physical disability.

16.  Learn about America’s RVs at a niche museum

Driving time from Chicago: About two hours 

Get inspired to embark on your version of the great American road trip as you browse permanent collections of trailers, motorhomes, housecars and more ranging from the 1910s to present at Elkhart’s RV/MH Hall of Fame (RV/MH stands for recreational vehicle and manufactured housing). Step back in time with Instagram-worthy vintage airstreams, Model T campers and motorhomes that look like they stepped off the set of Stranger Things . After your visit, explore the thousands of archives at the RV/MH Library, where you can glimpse into the recreational lives of North Americans in the 1960s issues of Trailer Life or 1980s issues of Camping Today .

17.  Visit Frank Lloyd Wright's home and studio

Just outside the city limits is the birthplace of Frank Lloyd Wright’s iconic architectural style. Early design concepts are filled in Wright’s Oak Park home and studio, with the surrounding residential district containing the most Wright-designed homes in the world. Visitors can enjoy a guided interior tour of the residence as well as a walking tour of the neighborhood for just $30 per person. Afterwards, pick up your favorite breads and pastries at Publican Quality Bread's Oak Park outpost.

18.  Take a picture with a (smaller) Leaning Tower of… Niles

Driving time from Chicago: About 25 minutes 

Sitting at a half the size its original at 94 feet tall and leaning 7.4 feet, the replica of the Leaning Tower of Pisa in suburban Illinois is an unlikely site and guaranteed out-of-the-box day trip. In the 1930s, a local businessman wanted to disguise a water tower and the answer was—obviously!—to craft a leaning tower. Taking an illusion photo holding up the tower is a must, and if you’re not too tired, head to nearby North Branch Trail and surrounding forest preserves for nature spotting or cozy up with your next great read at New Book Joy .

19.  Watch an outdoor play at American Players Theatre

Driving time from Chicago: About three and a half hours

Spring Green, Wisconsin is perhaps best known as the home of Taliesin, Frank Lloyd Wright's Prairie style summer estate set amid the limestone outcroppings of Wisconsin's Driftless Area. You should make a stop at the house if you have time—Wright's estate offers a huge variety of guided tours—but the 1,089-seat outdoor ampitheater at American Players Theatre is an equally unbeatable summertime attraction. The company's repetoire is mostly classical , though you'll find more contemporary works on the lineup as well.

20.  Celebrate Christmas in July at Santa’s Village

Driving time from Chicago: About an hour

Sure, Six Flags is fun, but there's only one suburban amusement park where you'll run into Santa Claus year-round, and that's Santa's Village Azoosment & Water Park in East Dundee. Despite its wintry theme, the family-friendly park is best visited in summer: Splash around in the Caribbean Christmas-themed Santa Springs water park—featuring two 300-foot, candy cane-colored slides—or take a spin on thrill rides like the Blizzard, which swings riders 40 feet in the air on a spinning pendulum.

21.  Eat fried chicken on Historic Route 66

Driving time from Chicago:  About 35 minutes

Fried chicken with a side of history? We’ll take it. At Dell Rhea’s Chicken Basket, you’ll be eating food that has been satisfying hangry travelers and folks simply looking for a good meal since 1946. This gas station lunch counter-turned-dining room is conveniently located off Route 66, its gleaming lights a beacon for those traveling to or from Chicago. Listed on the National Register of Historic Places, step into the nearly unchanged brick building and devour a Famous Fried Chicken Dinner, hand breaded and deep fried half chicken served with mashed potatoes and biscuits.

22.  Say “prost” in Germantown, WI

Despite its name, the Milwaukee suburb of Germantown, Wisconsin doesn't quite have the transportative qualities of other places in the Midwest that look like Europe . Still, there's a lot to love about this historically German settlement—sip a stein full of Krombacher Pils at the Von Rothenburg Bier Stube , check out more than 5,000 antique bells at the Sila Lydia Bast Bell Museum & Fire Hall or don your best lederhosen/dirndls for Maifest, the annual three-day festival held in honor of the beginning of spring.

23.  See some giant things in Casey, Illinois

Just under four hours south of Chicago, the intriguing town of Casey prides itself on being filled to the brim with giant things—literally. The town is home to 12 of  world’s largest items . From a 28-foot Chevy truck key to a 42-foot long wind chime to a 46,000-pound rocking chair behemoth, these public sculptures are really one-of-a-kind.

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12 Super Road Trip Destinations from Chicago for Spring Break

Sunday, january 23, 2022.

12 Super Road Trip Destinations from Chicago Perfect for Your Next Adventure

With warmer days hopefully upon us soon, time is here to think about road trips! I am sharing a few of my favorites within a range of distances.  Happy trekking!

Within 3 Hours

Galena, Illinois: Downtown Galena enchants with one of the most beautiful historic districts in the USA. The bustling downtown full of shops, wineries, eateries and history beckons wanderers. Nearby hiking experiences are plentiful and treat to fantastic views of the Mississippi including from one of our favorites, Mississippi Palisades State Park . The Ulysses S. Grant is home is one of our favorites to tour and includes so many authentic family artifacts. While in Galena, wander over to nearby Dubuque, Iowa for a trip up the Fenelon Place Elevator. 

Madison, Wisconsin: Wisconsin's state capitol, Madison , unfolds an amazing opportunity for a family getaway. The Wisconsin State Capitol Building is striking and quite an interesting place to tour. Don't forget to step out on one of the balconies for a view. A plethora of hiking opportunities exist in and around the city including Lakeshore Nature Preserve, Blue Mound State Park, Devil's Staircase and Pheasant Branch Conservancy. Olbrich Botanical Gardens enchants in all seasons. Chazen Museum of Art, Madison Children's Museum and Wisconsin History Museum all add to any itinerary. We also love nibbling at the bakeries in Madison including Madison Sourdough and Batch Bakehouse. 

Quad Cities, Illinois and Iowa: The Quad Cities incorporates a number of Illinois and Iowa communities saddling the striking Mississippi River. A wealth of nature activities can be enjoyed including hiking and bird watching on Sylvan Island, at Black Hawk Historic Site, at Illiniwek Forest Preserve and more. Putnam Museum and Science Center, Figge Art Museum and Quad Cities Botanical Center offer more avenues of discovery. Don't forget to pick up ice cream at Whitey's or Lagomarcino's. For the over 21 crowd, hit the Quad Cities Ale Trail. We love the wealth of activities available and return to the Quad Cities again and again!

Within 6 Hours

Columbus, Ohio: Columbus has been one of our favorite cities to wander. We love German Village full of historic buildings and small businesses. Visiting Schmidt's Restaurant rewards with fabulous and authentic German fare. (My favorite is the German chocolate pie.) Museums include the Center of Science and Industry with a dinosaur gallery, Columbus Museum of Art and Central Ohio Fire Museum. We also enjoy visiting the Columbus Zoo and Aquarium which has one of the best African savanna experiences I have viewed.

Grand Rapids, Michigan:   Grand Rapids is home to one of my favorite botanical gardens and sculpture parks, Frederik Meijer Gardens & Sculpture Park. the grand scale sculptures are breathtaking and the gardens awe especially the Japanese garden. We also find the Grand Rapids Public Museum and Grand Rapids Art Museum fascinating. We usually pair a trip to Grand Rapids with a trip to Lake Michigan's shore often at Grand Haven. I am totally a beach lover in all seasons and often prefer spring for visits because there are fewer visitors. Rosy Mound Natural Trail in Grand Haven is one of our cherished nature highlights.

Hocking Hills, Ohio: Hocking Hills State Park in Ohio fascinates with a cache of unique hikes exploring canyons, caves, cliffs, waterfalls and much more. We love renting a cabin in the region for a little nature respite away from it all.

Louisville, Kentucky:   Louisville offers a great launching point for a Kentucky vacation. Museums including the Louisville Slugger Museum & Factory and Frazier History Museum present venues entertaining a range of interests. Churchill Downs is iconic. Louisville Mega Cavern bestows a venue for weaving through ropes courses and sliding along ziplines underground. The food scene includes so many of our favorites including Mark's Feed Store and Homemade Ice Cream and Pie Kitchen. The Camberly Brown and Seelbach hotels sweep you back to old hospitality. Of course, bourbon is a must for the 21+ crowd.

Shawnee National Forest: Shawnee National Forest in Southern Illinois welcomes travelers to unique hikes with unparalleled views. The forest includes a remarkable 289,000 acres of nature adventures to experience. Hiking, camping, horseback riding, biking, fishing, climbing, boating and more forge incredible nature experiences in some of the most unique settings of the Midwest.

St. Louis, Missouri:   St. Louis is an ideal location for a little getaway right along the mighty Mississippi River. The City Museum, St. Louis Science Center, St. Louis Zoo and St. Louis Art Museum among others inspire discovery. Of course, visitors must check out the Gateway Arch! Eating on 'The Hill' will treat you to fantastic Italian fare. You will also be near Cahokia Mounds where you can learn about the Mississippian Mound Builders. Additionally, you can head to St. Charles or Ste. Genevieve for a little French colonial history. When in St. Louis, one must also take an Anheuser-Busch Brewery Tour.  So many avenues of exploration make St. Louis a fabulous destination.

Within 8 Hours

Minneapolis and Saint Paul, Minnesota:   Minneapolis and Saint Paul have always been a favorite locale to visit. I love that there are spaces to admire nature right in Minneapolis and St. Paul including Minnehaha Falls, Chain of Lakes and Shadow Falls. Plus, there are tons of hiking opportunities nearby in Minnesota and Wisconsin. Mill City Museum and the Museum of Russian Art are two of my favorite museums in the Midwest. A walk along the Stone Arch Bridge and a peek at flour mill ruins provide an interesting look at Minneapolis. Como Zoo Conservatory in nearby Roseville treats to magnificent floral displays in all seasons. The region is populated with local microbrews adding tasting experiences.

Omaha, Nebraska: Perched along the Missouri River, Omaha offered us a wonderful starting point for a few nature adventures including Platte River State Park, Lewis and Clark Monument Park, Heron Haven and more. We loved walking around the Old Market, peeking into the Passageway and more. The city includes a wealth of museums such as the Durham Museum, Joslyn Art Museum, Omaha Children's Museum present a wealth of adventures.  For a truly unique scene, visit Hollywood Candy which not only delights with tons and tons of candy but includes a vintage pinball arcade, movie memorabilia, a '50s diner, vinyls and so much more!

Pittsburgh, Pennsylvania: Pittsburgh is a fantastic vacation choice for any season. The city's range of museums inspires any wanderer. The National Aviary is a wonder that should not be missed. Several rooms are free-fly, so you will have all sorts of interesting birds freely flying and roaming. Andy Warhol Museum, Heinz History Center, Carnegie Museum of Natural History and more will invite exploration. Don't forget to take the Duquesne Incline up to the top of Mount Washington for a view. We have to take in this view EVERY time we are in the city. Wander the Strip District for all sorts of foodie treats and shops. Hiking, river views and more will entice nature lovers. Every trip to Pittsburgh welcomes us to new experiences.

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Travels & Treasures

A Complete Guide for a Chicago Road Trip

Packing for a Chicago road trip is a great way to explore the metropolis, scout the neighborhoods, soak in the breathtaking views, and create memorable experiences. 

If you’re planning a road trip to Chicago, the Windy City, it’s essential to be well-prepared to make the most of your adventure. 

Since I have lived and driven in the Chicago area for over 30 years, you can use this guide that I created to help you through the essential items to pack, tips for driving in Chicago, road safety tips, and more. 

So, fasten your seatbelts and get ready for an exciting journey!

Table of Contents

Essential Items for a Chicago Road Trip

Firstly, let’s get the obvious items out of the way. Although they apply to just about any road trip, I think it’s important to keep this in mind for Chicago too.  

• Comfortable Clothing : When starting your road trip, opt for comfortable clothes that are suitable for long hours of sitting. Choose breathable fabrics, such as cotton, and consider layering to adapt to changing temperatures during your road adventure.
• Weather-appropriate Gear : Depending on the time of year, Chicago’s weather can be unpredictable, so pack accordingly. In spring and fall, you will want to layer your clothing. Bring a light jacket or sweater, a raincoat or umbrella, and hats and gloves for colder seasons.
• Snacks and Drinks : Keep yourself fueled during the drive with a variety of snacks like granola bars, fruits, nuts, and bottled water. During summer, bring a cooler for the trip to stay hydrated and to store perishable items. It will also save you time and money so that you don’t have to stop and spend extra dollars at pricey convenience stores. 
• Navigation Tools : Ensure a smooth journey by bringing a GPS device or using a reliable navigation app on your smartphone. For your road trip, you could have a physical map or printed directions that serve as backup.
• Entertainment Options : Long road trips can be tiresome, so pack entertainment options like books, podcasts, or audiobooks. Prepare playlists with your favorite music to keep the atmosphere lively. Also, pack some games and movies or have a list of engaging car games prepared for the little ones when traveling on a road trip. 
• Roadside Emergency Kit : Prepare for unexpected situations by carrying a roadside kit. It’s always wise to be prepared for any emergencies on the road. Put together a roadside emergency kit that includes a spare tire, jack, jumper cables, flashlight, first aid kit, basic tools, and a roadside assistance contact number. Additionally, consider adding a portable phone charger and extra batteries to stay connected.

Tips for Driving in Chicago

When it comes to driving in Chicago, there are a few things that people might not know. First and foremost, be prepared for the notorious traffic congestion, especially during peak hours.

Chicago has a public transportation system. I advise that you use it as much as possible because it will save you time and money especially during peak season , while visiting the city.

Peak Traffic Hours

The morning peak hours going into Chicago are between 6 AM and 9 AM. The peak hours leaving Chicago are between 3 PM and 7 PM.

The evening hours extend just a bit because some like to visit happy hour events, so the peak period is a tad longer.

Anytime outside of these hours are generally OK for driving except for popular sports events like a Bulls or Bears game, a concert, or other city-hosted events like parades and large festivals.

Also, note that Chicago is a bustling city that does a lot of business, so you will have to contend with semi-trucks, delivery vans, and heavy-duty trucks.

Construction

There is a saying in Chicago that “There are two seasons of the year, winter and construction.”

Plan your driving around the peak traffic hours and look for alternate routes via GPS. Even if you have extra time, don’t take it for granted.

Delays during construction are inevitable (and frustrating when the traffic is reduced from 4 to 1 lane)! There may also be delays caused by unexpected accidents or slowdowns caused by emergency vehicles.

Parking is always a challenge in the city and it’s very expensive and fees for parking violations are hefty. The best way to locate a garage is via SpotHero.com. You can find discounted fees for early arrivals (before 7 AM) but the hours you are allowed to stay for the discounted price is usually limited.

If you are staying in the downtown area and have a parking spot, I suggest you leave the car and use public transportation during your stay. Getting around Chicago is very easy, and you will save more money by avoiding the expense of additional parking.

If you do need to use a car, familiarize yourself with street parking regulations. There is rarely free street parking and just about every parking space downtown is metered. Look for the meter posts near the end of each block to pay for parking. The machines accept cash and credit cards.

When parking in neighborhoods, you will find that some require a permit or vehicle sticker. In winter, the lack of snow removal makes it difficult to find parking so residents will “reserve” spots with chairs, cones, or anything they can find. My advice is to avoid using these spots or you may risk retaliation.

Lastly, if driving in Chicago intimidates you, stay in the right-most lane or use the side streets. Avoid the road rage caused by speeding drivers who don’t use good driving etiquette. Try not to block cars who are trying to cross the main road from alleys, parking lots, or turning lanes.

Keeping these lesser-known aspects in mind will help ensure a smoother and stress-free driving experience in the bustling streets of Chicago.

Road Trip Safety Tips

While embarking on a road trip to Chicago, it’s crucial to prioritize safety. Read further for some essential safety tips to ensure a smooth and secure road trip.

Check Your Vehicle Condition

Before hitting the road, inspect your vehicle’s tires, brakes, lights, and fluids. Ensure everything is in good working order and consider getting a professional mechanic to perform a thorough inspection.

Plan the Route

Plan your route in advance, considering traffic conditions and any road closures. Utilize GPS navigation or maps to avoid getting lost and save time.

Share Your Itinerary with Family and Friends

Inform a trusted friend or family member about your road trip itinerary. Provide them with details of your planned route, accommodation, and expected arrival times. This way, someone will be aware of your whereabouts. Looking for more to do? Review some recommendations in our ultimate guide to Chicago .

Take Regular Breaks

Long drives can be tiring, so take regular breaks to stretch your legs, have a snack, and rest. Fatigue can impair your driving abilities, so it’s essential to stay alert and well-rested.

Stay Alert and Avoid Distractions

Keep your focus on the road and avoid distractions such as texting, eating, or adjusting the radio while driving. Remember, safety should always be your top priority.

Follow Traffic Laws

Observe and follow all traffic laws and regulations, including speed limits, seatbelt usage, and traffic signals. Be mindful of other drivers and pedestrians to ensure everyone’s safety on the road. When in doubt, review the rules of the road for Illinois .

Itineraries by Car: Scenic Drives in Chicago

Once you’ve reached Chicago, there are several iconic attractions you shouldn’t miss. Here are some must-see places that will make your road trip unforgettable.

Lake Shore Drive

Take a leisurely drive along Lake Shore Drive, which stretches along the beautiful shoreline of Lake Michigan. Enjoy stunning views of the lake, the city skyline, and iconic landmarks like Navy Pier and Grant Park.

Lake Shore Drive is about 16 miles long. You can start at 67th Street in the South Shore neighborhood and goes north to Hollywood Avenue.

The Magnificent Mile

Cruise along North Michigan Avenue, known as the Magnificent Mile. Marvel at the impressive architecture, luxury boutiques, and iconic landmarks as you drive through this bustling shopping district.

The Magnificent Mile is one mile long and starts at the Chicago River and extends north to Oak Street Beach .

The Outer Drive

The Outer Drive is also known as South Lake Shore Drive. This scenic route takes you through the southern part of the city, offering picturesque views of the lake, harbors, and the Museum Campus which consists of The Field Museum, the John G. Shedd Aquarium , and the Adler Planetarium.

The Outer Drive starts at East Jackson Drive and extends south to East 67th Street. It is in the southern part of Lake Shore Drive.

Green Bay Road

Head north of the city and take a drive on Green Bay Road. This road offers a scenic journey through the charming suburbs, lined with beautiful homes, parks, and quaint downtown areas.

Green Bay Road extends through the northern Chicago community and multiple northern suburbs including Evanston, Skokie, Wilmette, Winnetka, Glencoe, Highland Park, Lake Forest, Waukegan, and Zion. These are great towns to explore outside of Chicago during your road trip.

Sheridan Road

Embark on a drive along Sheridan Road, which runs parallel to Lake Michigan. This picturesque route takes you through charming neighborhoods, historic mansions, and scenic lakefront parks.

Sheridan Road extends through the northern Chicago community and multiple northern suburbs including Evanston, Wilmette, Kenilworth, Winnetka, Glencoe, Highland Park, Lake Bluff, Lake Forest, North Chicago, and Waukegan. You make want to include a visit to some of these towns during your Chicago road trip.

Chicago Skyway

Experience a unique perspective of the city by driving on the Chicago Skyway. This elevated toll road offers fantastic views of the downtown area and provides a smooth route to the neighboring state of Indiana for a day drive.

FAQs for a Chicago Road Trip

What is the driving distance to chicago.

The driving distance to Chicago varies depending on your starting point. Use a reliable navigation tool or map application to get the most accurate distance information.

Are there any tolls on the way to Chicago?

Yes, there are tolls on some highways leading to Chicago. Make sure to carry cash or have an electronic tolling device like an I-PASS or E-ZPass for seamless travel.

How many days should I plan for a Chicago road trip?

The ideal duration for a Chicago road trip depends on your interests and the attractions you want to explore. A minimum of 3-4 days is recommended to cover the major highlights, but extending your stay allows for a more immersive experience.

Can I find parking easily in downtown Chicago?

Parking in downtown Chicago can be challenging, especially during peak hours. It’s advisable to research parking options in advance of your road trip and consider using public transportation or ride-sharing services to navigate the city.

What are some offbeat attractions in Chicago?

Apart from the popular landmarks, you can explore offbeat attractions like the Garfield Park Conservatory , and 360 Chicago Observation Deck, or take a street art tour in neighborhoods like Pilsen and Wicker Park.

Final Thoughts on a Chicago Road Trip

A road trip offers an incredible adventure filled with iconic Chicago attractions , delicious food, vibrant culture, and memorable experiences.

By packing essential items, following safety tips, and planning your itinerary, you can make the most of your journey.

Don’t forget to create your Chicago road-trip itinerary or read some of our recommendations for a perfect blend of vacation activities , iconic sights, cozy accommodations, and unique experiences.

Explore Millennium Park and Navy Pier, dive into the city’s vibrant culture, and immerse yourself in art at the Art Institute of Chicago .

When it comes to accommodations, choose from downtown hotels for convenience or boutique options for a personalized touch. Experiencing one of the best neighborhoods in Chicago will also create a memorable stay.

Indulge in deep-dish pizza (don’t forget to invite me), take an architecture boat tour , and catch a thrilling sports event. Chicago offers a road trip experience like no other, where every moment can be filled with excitement and discovery.

Tanya, a travel writer and content creator who has lived in Chicago for over 30 years, is your go-to local expert for Chicago's hidden treasures. Tanya's deep knowledge of various cities and attractions is acquired through personal exploration, making her articles a treasure trove for travelers and families. She has visited 43 of the 50 United States, France, Italy, Spain, Portugal, and the UK.

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12 Best Spring Break Road Trips from Chicago

Chicago is known for its world-class museums, including the Field Museum and the Museum of Science and Industry, but after the cold Chicago winter, most people will have exhausted the city's many indoor attractions. That makes spring break the perfect time to take a trip.

Whether you have a day, a weekend, or longer, there's a fabulous choice of spring break trips from Chicago. Drive to Cincinnati, Traverse City, Cleveland or Columbus, follow Scenic Route 61, or chase the sun south the Nashville, Hot Springs or Atlanta.

There's something for everyone in reach of Chicago, with great spring break road trips to suit if you're traveling with children, teens, or childfree. Keep reading to find out some of the best places you can get to from the Windy City this spring break.

Best spring break road trips from Chicago

Chicago makes a great place for a spring break staycation, and with its museums, parks and the attractions around Navy Pier to enjoy you might even be heading there as your main spring break destination. But if you're ready to explore a little further afield after the St Patrick's Day party, or looking for a day trip or two while you spend spring break in Chicago itself, you have some amazing destinations to choose from.

After the long winter, why not head out for an adventure when spring break rolls around again? We've listed some of our favorite spring break destinations, so keep on reading to decide what kind of trip awaits you this spring break.

If you're thinking of taking a road trip from Chicago in another season, check out our Best Road Trips from Chicago article for ideas and inspiration! We also have a detailed guide for traveling from Chicago in winter, if you want to plan ahead.

Day trips (about 3 hours each way)

1. Indianapolis, Indiana

3 hours 10 minutes from Chicago (180 miles)

Why you should visit: This is the shortest trip on the list, but there's plenty to see in the city whether you're traveling as a family with young kids or taking a break from college.

The Children's Museum is sure to be a hit for younger travelers – it's the world's largest children's museum. With a visit here your spring break can take you to modern Europe, ancient Egypt, or even into space.

Baseball fans might like to time the trip to catch the home opener of the Indianapolis Indians, which usually takes place in early April.

How to get there: Head out of Chicago on I-90 E then pick up I-65 which you'll follow south past Remington and Lafayette. After around 130 miles on the interstate you'll cross the White River to arrive in downtown Indianapolis.

Our highlights: The Indianapolis Children's Museum will definitely appeal to families on spring break. This huge space has engaging interactive exhibitions covering space travel, history, pop culture, science and technology, and dinosaurs.

Families and college athletes alike will also appreciate the NCAA Hall of Champions, which even has sports simulators where you can try your hand at new activities.

Elsewhere, Indianapolis Museum of Art blossoms in springtime when the thousands of bulbs planted at Newfields' gardens burst into life.

Indianapolis also has breweries, wineries and distilleries which you can visit with the Indy Craft Pass – something that might appeal if you want to party during spring break.

Bonus: You won't be able to see the famous Indy 500 automobile race during your spring break visit, as this usually takes place in May. If you decide to make a return trip to see the race, you'll be in good company – more than half a million people watch from around the Speedway.

Our travel tips: Weather can be variable during spring break, from 32 degrees F right up to 65 degrees. April is one of the wettest months of the year too, so pack accordingly.

2. Springfield, Illinois

3 hours 30 mins from Chicago (200 miles)

Why you should visit: This is a really easy drive out from Chicago, and with its presidential history it's a fascinating contrast to the Windy City. It's also a great place to spend a weekend, especially if you fancy following the Capital City Bourbon Journey.

Springfield is a great family getaway, especially if your kids have started to learn about the country's history.

You can immerse yourself in stories of the country's 16th President, Abraham Lincoln, who lived in the city for many years – his legacy as the country's Civil War-era president is sure to inspire grade schoolers and older teenagers alike, especially when you can visit the places where he lived and worked for real.

How to get there: This is a really simple trip to navigate – just pick up I-55 S from your departure point in Chicago, and follow it all the way to Springfield, Illinois.

Our highlights: You could easily spend the whole trip exploring Lincoln-related sites. There's the Lincoln Home National Historic Site, where he lived until becoming President in 1861, and the unique, interactive Abraham Lincoln Presidential Library and Museum. You can also tour both the old and new state capitol buildings.

Younger kids will enjoy Kidzeum, a colorful museum where they can learn about keeping themselves and the planet healthy. Many of the exhibits are play-based – a perfect pick-me-up if they're getting fidgety after all that history.

With its vintage fighter planes, the Air Combat Museum might also appeal. Check ahead for opening times.

Alternatively, if you need to run off some energy, head to Knights Action Park, where you'll find arcade games, rides and mini-golf.

Springfield isn't just for families though – older visitors might like to follow the Capital City Bourbon Journey, which takes you on a tour of some fabulous bars and restaurants to try locally-produced makes.

Bonus: Springfield didn't invent the corn dog, but it does claim to be the birthplace of the iconic cozy dog – that's a hotdog on a stick covered in tasty batter for out-of-towners. For one of the best in town, head to the Cozy Dog Drive-In.

Our travel tips: Springfield will feel chilly if your spring break falls earlier in the season, with March temperatures rarely topping 50 degrees Fahrenheit. You might even see a little snow.

Click here to skip back to the top.

Weekend trips (about 5 hours each way)

3. Cincinnati, Ohio

5 hours from Chicago (290 miles)

Why you should visit: Cincinnati is a beautiful riverside city which is at the longer end of the one-day range – it's also a great place for an overnight trip. There's plenty going on so it will appeal to visitors of all ages.

If your spring break coincides with Opening Day, come and join the party in Cincinnati. With unbeatable baseball heritage, the first pitch of the season sees the Findlay Market Parade and other events to celebrate the Reds (who always play their opening game at home).

How to get there: Follow the interstate as far as Indianapolis. You can stop for a break here but if you'd rather head straight to then bypass the city on I-465 which takes you onto I-74. Follow this road all the way to Cincinnati.

Our highlights: Baseball fans should head straight to the Cincinnati Reds Hall of Fame & Museum, where you can also take a tour of the Great American Ballpark.

If you're not in town for Opening Day, there's still plenty to see and do. Cincinnati Zoo holds its popular free Tunes & Blooms sessions on Thursday evenings through April. Enjoy live music among the colorful spring blooms in a family-friendly atmosphere. You can also enjoy the blooms in the daytime if you need to hit the road back to Chicago by the evening.

At Krohn Conservatory, the spring sees the arrival of thousands of butterflies which are fascinating to watch when you visit the tropical glasshouse.

With its Dinosaur Hall and interactive science exhibits, Cincinnati Museum Center is also a great family day out. Head to the Children's Museum for some play-based fun.

Bonus: For many years, the baseball season was officially opened with a first pitch in Cincinnati, whose team, the Reds, was the first in the country to go fully professional.

Our travel tips: The city will be really busy if you do visit for Opening Day, so expect some queues and leave extra time to park (we'd suggest arriving early). Book early if you want to try to get tickets for the game.

4. Traverse City, Michigan

5 hours from Chicago (320 miles)

Why you should visit: This is the only destination on our list that lets you carry on exploring the shores of Lake Michigan.

After the long winter, the wildflowers start to blossom around Sleeping Bear Dunes National Lakeshore, making this a fabulous weekend destination for fans of the great outdoors.

How to get there: The interstate runs parallel to the shore of Lake Michigan most of the way to Traverse City. You'll start out on I-90 E before switching on to I-94. Follow this past Benton Harbor then change onto I-196 where the interstate divides. When you reach Grand Rapids join US-131 and continue north until you reach your destination.

Our highlights: You could spend days exploring the fabulous lakeshore, but seeing as you're only here for the weekend we'd suggest starting at Sleeping Bear Dunes with a hike along the Old Indian Trail or spending some time exploring Old Mission State Park. You can also visit the historic lighthouses – six in all – to enjoy more atmospheric views out across the lake.

It's too early in the year to swim in the lake but kids of all ages will love the huge indoor water park at Great Wolf Lodge.

If you're here without the family, visit a winery or two or taste some of the wine produced along the Traverse Wine Coast at one of the city's tasting rooms or bars.

Bonus: Traverse City is known as the Cherry Capital of the World. Spring break is out of both the cherry blossom and picking seasons, but don't miss the chance to try a slice of cherry pie while you're in town.

Our travel tips: Temperatures often dip below freezing even in April, and this can be a wet time of year, so plan for some indoor activities if you're making a spring trip here.

5. Columbus, Ohio

5 hours 30 mins from Chicago (350 miles)

Why you should visit: Ohio's state capital and largest city is packed full of things to do during spring break. The length of the drive means you'll probably want to stay at least a night (or maybe longer) but there's so much to do when you arrive that you definitely won't be bored.

You'll find a whole host of family-friendly attractions in Columbus, including one of the best science museums in the country at the Centre of Science and Industry.

How to get there: Follow I-65 away from Chicago then at Indianapolis change onto I-70 to head east into Ohio. As you approach Columbus, merge onto I-670 to make your way to the downtown area.

Our highlights: The Center of Science and Industry (COSI) – named "America's number one science museum" – is packed full of interactive and informative exhibits which are guaranteed to keep children entertained for hours.

Another surefire hit with children is the LEGOLAND Discovery Center. It doesn't just appeal to kids, though. There's a 3D cinema featuring Lego characters, as well as the chance to build and explore interactive displays.

Just outside town, Columbus Zoo & Aquarium is another entertaining attraction, and if your spring break coincides with Easter there are extra egg-themed activities and attractions

If you're feeling active, head to Hocking Hill State Park, where you can escape the busyness of the city and hike through a fascinating sandstone landscape.

Staying outside, you can also visit Franklin Park Conservatory & Botanical Gardens, where the spring flowers will be starting to burst into life. It's a relaxing place to escape the hustle and bustle, and if you're traveling as a family children love exploring the tropical conservatory too.

Finally, to celebrate the spring sunshine, round off the afternoon or evening on one of the city's rooftop patios.

6. Cleveland, Ohio

Why you should visit: As well as spending time by another of the Great Lakes, this trip from Chicago to Cleveland also lets you follow one of “America's most scenic drives” with a detour along Indiana's Heritage Trail that starts at Elkhart.

If your spring break falls over the Easter period, come and join in the Dyngus Day celebrations! Held on Easter Monday, this Polish festival includes polka dancing, accordion music and beer tents – a really unique way to spend the spring break whatever your age!

Another interesting event that coincides with spring break is the Cleveland Thyagaraja Festival, a celebration of Indian classical music that brings international stars to the city.

How to get there: From the center of Chicago, join I-90 and keep going. You'll drive all the way across Indiana and then into Ohio, passing to the south of Toledo and Lake Erie before arriving in Cleveland.

If you're following the marked Heritage Trail, leave the interstate at Elkhart then head east on IN-120 to Bristol. Carry on to Middlebury and Shipshewana before looping back around to visit Goshen and Nappanee. Wakarusa is the final stop on the trail, which then passes through Elkhart again before you rejoin I-90 to continue east towards Cleveland.

Taking this detour along the Heritage Trail will add around 2 hours and 30 minutes to your driving time, plus any time for stops in the towns you'll pass along the way.

Our highlights: On your way to Cleveland, take a break from the interstate to travel along Elkhart County's Heritage Trail. Taking you through small towns and beautiful landscapes, you can download a free audio guide which gives you some of the background to this peaceful part of Indiana.

Once you've arrived in the city, you should definitely try out Maple Sugaring if you're visiting in March. This takes place at a number of locations in and around Cleveland.

If you're traveling with children, check out the themed trips on the Cuyahoga Valley Scenic Railroad, which run through April.

If the weather's good enough to spend more time outdoors, go for a longer hike through Cuyahoga Valley National Park where Brandywine Waterfall should be in full flow. You could also spend a peaceful half hour walking through the daffodils that carpet Lake View Cemetery.

Bonus: Cleveland Thyagaraja Indian classical music festival is the biggest festival of its kind that you'll find without visiting India.

Our travel tips: As with some of the other destinations listed so far, spring weather in Cleveland can be unpredictable, ranging from late snow to bright sunshine.

READ MORE - Road Trip from Chicago to Cleveland

Long weekend trips (6-8 hours each way)

7. Nashville, Tennessee

7 hours 15 mins from Chicago (480 miles)

Why you should visit: Nashville is the first of our road trip destinations where you're likely to be able to enjoy some warmer spring weather, and the first one outside the Midwest.

Nashville is a great place to party , and with live music and warm weather likely to feature, it's perfect for a short spring break road trip from Chicago. It's a straightforward interstate drive south for the weekend, and once you arrive, you can immerse yourself in the party atmosphere until it's time to leave.

It's also a fun place to take children, especially if they're happy to soak in the atmosphere. Many of the live venues on Lower Broadway welcome families during the daytime.

How to get there: Although it's a pretty long drive, this 475-mile route is really easy to navigate. Just hop onto I-65 as you exit Chicago to the south, and follow it all the way through Indiana and Kentucky. Just after you cross the Cumberland River, turn onto I-40 to make your way into Nashville's downtown where you'll complete your drive.

Our highlights: You can't visit Nashville without seeing a live show or two, so head to Music Row and take your pick before partying late into the night on Broadway. Some venues host special spring break parties, but if these don't match the kind of vibe you're after there are plenty of other venues to choose from.

A great all-year-round attraction that's a must-see in Nashville is the Country Music Hall of Fame. If really you want to immerse yourself in the heritage of Music City, you can carry on to the Johnny Cash Museum, RCA Studios or the Grand Ole Opry House.

When you're ready to take a break from wall-to-wall music, head to the Cheekwood Estate where the springtime Cheekwood in Bloom event sees over 100,000 tulip bulbs filling the peaceful gardens with bursts of color.

Just outside the city, Treetop Adventure Park is great for couples, groups and families alike – test your nerves as you travel across bridges, ropes and ziplines high up in the canopy (children must be over 7 to take part, and an adult has to climb with them).

Bonus: Book a stay at the Gaylord Grand Ole Opry Resort to enjoy a host of springtime activities for families.

Elvis recorded dozens of songs in Nashville, and with so many live acts performing in the city, you might one day be able to say you saw the next big music star before they were famous.

Our travel tips: This part of Tennessee is known for its spring tornadoes. It's unlikely that you'll see one but watch out for local advisories while you're in town.

Even this far south you'll need to pack warm clothes as the evenings will be cool and the weather can still sometimes be unsettled, especially in early spring.

READ MORE - Road Trip from Chicago to Nashville

8. Knoxville, Pigeon Forge and Gatlinburg

8 hours from Chicago (550 miles)

Why you should visit: With the mild Tennessee spring weather in your favor, you can leave your winter gear behind and enjoy time in the great outdoors on this trip.

The Great Smoky Mountains will be bursting with color in the spring, from the lush new leaves on the trees to the carpet of wildflowers.

In between the winter snow and sometimes humid summer heat, spring break is the perfect time to lace up your hiking boots and explore. If you need to keep teens or older kids entertained too, the fun attractions at Gatlinburg and Dollywood will be just the ticket.

How to get there: Follow the route toward Cincinnati along I-65 and I-74, then take I-275 to bypass the city itself. You'll cross the Ohio River to enter Kentucky, then follow the interstate south towards Lexington. Continue along I-75 and you'll reach Knoxville around an hour after crossing the state border into Tennessee.

To reach Pigeon Forge and Gatlinburg, take I-40 out of Knoxville then turn south on TN-66. From Sevierville, turn onto Parkway which takes you to both towns. This part of the trip will add just over an hour to your drive time.

Our highlights: While you're in Knoxville, enjoy the city's nightlife under the beautiful dogwood blossoms, and check out April's Chalk Walk which sees colorful art on sidewalks across downtown.

When you're ready to head out of town, make for Great Smoky Mountains National Park where trails and lookouts are abundant, or follow the Newfound Gap Road for a spectacularly scenic drive through the mountains.

Just outside nearby Pigeon Forge, Dolly Parton's Dollywood amusement park is a firm favorite with visitors of all ages.

Thrill seekers should definitely head to Gatlinburg's Mountain Coaster, which races rollercoaster-style down the side of the mountain, or Smoky Mountain Ziplines, where you can get a whole new view of this beautiful part of the world.

Bonus: Great Smoky Mountains National Park receives more visitors than any other national park in the United States – more than 11 million a year.

Our travel tips: Because of its popularity the roads into the national park can feel a little crowded at busy times, especially during spring break. Parking lots fill up and you might hit traffic delays. Visit early in the day or in the evening if you want to avoid the crowds – you're also more likely to see wildlife at these times.

READ MORE - Road Trip from Chicago to the Great Smoky Mountains National Park

Longer trips (Over 8 hours each way)

9. Chattanooga, Tennessee

9 hours 20 mins from Chicago (610 miles)

Why you should visit: Built around the Tennessee River and overlooked by Lookout Mountain, Chattanooga is a city where you can easily combine active adventures with big-city entertainment.

For a longer spring break trip, stop in Nashville as well to enjoy even more of Tennessee's southern charm and hospitality.

Attractions in Chattanooga put on special events as part of the Spring Break Safari, making the city the perfect family spring break destination. There are child-focused art, science and nature activities on the itinerary, as well as the chance to explore caves, ride the Tennessee Valley Railroad or visit the Tennessee Aquarium.

How to get there: Follow I-65 all the way to Nashville, where you'll merge onto I-24 after a brief stretch on I-40 as you cross the city. I-24 then takes you all the way to Chattanooga, crossing the Tennessee River Bridge then dipping into Alabama for about a mile before you complete your journey in the far south of Tennessee.

Our highlights: Tennessee Aquarium is one of the stops on the Spring Break Safari and the world's biggest freshwater aquarium. Check out the penguins, otters, and alligators, as well as plenty of underwater favorites.

The Creative Discovery Museum is a firm favorite with younger children. It features fun, interactive science-based exhibitions that will keep them entertained for hours.

Another must-see in Chattanooga is Ruby Falls, a waterfall and cave system which sits under Lookout Mountain. The mountain itself towers above the city and if you're feeling energetic you can hike right up to the top for amazing views across Chattanooga and into Georgia.

A great activity for families or groups of friends, you can take a small pedal-powered boat out to enjoy food and drinks on the Tennessee River.

Bonus: Miniature golf was invented in Chattanooga nearly a century ago, so why not play a round during your stay in the city?

Our travel tips: Chattanooga is notorious for its traffic so avoid traveling in the morning or evening rush hours if possible

10. Hot Springs, Arkansas

10 hours 40 mins from Chicago (700 miles)

Why you should visit: As well as being a great spring break destination, you can turn the drive to Hot Springs, AR, into a fabulous longer road trip with stops in Springfield and St Louis along the way.

People have been coming to Hot Springs in search of the healing powers of its naturally heated spring water for nearly 200 years, so if you're in need of some relaxation and downtime during spring break, this is the place to come.

How to get there: Follow I-55 southeast through Illinois, passing Springfield before you cross the Mississippi River at St Louis, Missouri. After following the interstate south out of the city, turn onto US-67 which winds its way through the gently rolling hills of Missouri and into Arkansas.

At the town of Corning, turn right to continue along US-67/US-62, sticking with US-67 when the highways divide at Pocahontas. At Bald Knob the road merges with US-167 which takes you to the state capital Little Rock. Follow I-30 W out of the city, then turn onto US-70 for the final stretch of your drive to Hot Springs.

Our highlights: Top on most people's list in Hot Springs is a visit to a spa or geothermal spring. There are plenty to choose from, depending on whether your want a traditional bathing experience or a full day of pampering and relaxation.

Bathhouse Row is a National Historic Landmark District where 8 historic bathhouses still stand. Most no longer operate as bathhouses, but at Buckstaff Bathhouse you can still experience the same hot spring bathing experience that the first visitors here in 1912 would have enjoyed.

If some of your group are less interested in spa time than others, Adventureworks Hot Springs is a more active alternative. Ride zip lines and tackle a treetop rope course.

Crystal Ridge Distillery offers informative tastings and free tours where you can find out about the history of the moonshine that's traditionally been produced in this part of the country.

Bonus: The mineral-rich water from the hot springs is said to have healing qualities, and there are fountains across the city where you can take a drink or fill a bottle.

If you happen to be in Hot Springs over St Patrick's Day you can watch “the world's shortest St Patrick's Day Parade”. The event travels less than 100 feet but features several lively Irish-themed entertainment acts.

Our travel tips: Although there are a few natural open-air pools where the hot spring water travels down the mountain, bathing in them is not permitted. You can only soak in the geothermal water at Hot Springs at indoor bathhouses and spas.

11. Highway 61 Scenic Drive

11 hours from Chicago (710 miles)

Why you should visit: This trip takes you right up to Grand Portage on the Canadian border, which is the northernmost point on our list.

Spring is one of the best times of year to see the Northern Lights, which are visible along this route. It's an unforgettable spectacle which is definitely worth the long drive out from Chicago. With the weather still feeling wintery, book into a cozy cabin and enjoy quality time together over spring break.

How to get there: Follow I-90 W out of Chicago for around 100 miles until you reach Wisconsin, then continue for another 100 miles to merge with I-94. From here the road takes you through Eau Claire before arriving in the twin cities of St Paul and Minneapolis.

Exit the city via I-35 W for a couple of miles, before continuing on I-35 N in the direction of Duluth. The interstate ends here and you'll complete your road trip by following Highway 61 Scenic Drive, which follows the shore of Lake Superior all the way to Grand Portage at the Canadian border.

Our highlights: If there is still snow on the ground, that means you can take a scenic dog sledding trip to explore the wild landscapes of the scenic north shore.

The scenic drive along the North Shore is one of the main attractions of this road trip, so make sure you leave plenty of time to stop and enjoy the views along the way.

If the snow has melted, pack your hiking boots and set out to explore Tettegouche, Temperance River or Cascade River State Parks, which are all easily accessed from Scenic Route 61 along the lakeshore.

At Lutsen you can ski in colder months or, if spring has come early when you visit, head up to the peak via gondola to enjoy stunning views.

Bonus: You can't drive this route without stopping off in Grand Marais to visit World's Best Donuts, a local legend.

Our travel tips: As you might expect this far north, temperatures can be cold especially if your spring break falls early in March. Heavy snow is possible but not guaranteed during March and April, so stay flexible in your choice of activities if you take this trip.

This trip is probably best suited for travelers who can visit a little later in the season if they want to comfortably spend more time outdoors.

12. Atlanta, Georgia

11 hours from Chicago (730 miles)

Why you should visit: Atlanta is the southernmost destination on our list and is an amazing place to visit from Chicago during spring break .

You're almost certain to enjoy some much-needed spring sunshine here, without the large crowds that you'll find further south in Florida or on the coast.

How to get there: Head south through Nashville to Chattanooga on I-65 and I-24. As you enter Georgia just south of Chattanooga, I-24 merges with I-75 which takes you as far as the suburbs of Atlanta.

Depending on your final destination in Atlanta, you'll probably join up with I-85 to complete your journey in the city's downtown.

Our highlights: Families should head straight to Centennial Park, a huge outdoor space which covers the site of the 1996 Olympic Park. The Children's Museum of Atlanta is on the edge of the park too.

Zoo Atlanta is a must-see for visitors of all ages. It's one of the only places in the United States where you can see Giant Pandas, alongside many other endangered species.

There's also a wealth of sites dedicated to modern US history and the Civil Rights movement in Atlanta, including the National Center for Civil and Human Rights and Martin Luther King Junior National Historical Park.

If you're traveling with older spring breakers, Six Flags Over Georgia theme park is a great stop, and sports fans should definitely check out the College Football Hall of Fame.

Bonus: Coca-Cola originated in Atlanta in the 1880s, which is why you'll find the World of Coca-Cola in the city today.

Our travel tips: “Rush hour” in Atlanta lasts all day. Allow plenty of time for your journey if you're using your car to get around the city.

READ MORE - Road Trip from Chicago to Atlanta

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4 Phenomenal Road trips to Chicago inc Interactive Maps!

Hit the road with our guide on 4 incredible Chicago road trips, complete with interactive maps and itineraries. Perfect for travelers craving scenic routes and tasty stops!

The Windy City, Chicago, Illinois is a large metropolis on the scenic Lake Michigan. The Skyline is punctuated with vast skyscrapers, such as the  Willis Tower (Former Sears Tower)  and the Legendary John Hancock Center at over 1,451ft high.

Chicago is also known for its tasty foods from Chicago style pizza (Deep dish) & mouth watering Chicago hot dogs. In addition, Chicago is know for its Jazz and of course the Notorious 1920s gangster Al Capone!

In this post i'm going to run through my top 4 most life changing road trips I've taken to or from Chicago! I've also included an interactive road trip map for each & Itinerary! So lets Dive right in!

4. New York City to Chicago Road Trip!

New York City and Chicago have always had a rivalry. Some say New York is just Bigger & Badder, while others point out that the Chicago people are just more friendly & laid back!

Me & my girlfriend were having this same dispute…so to settle any arguments we decided to to a road trip between New York City & Chicago and of course head past some great cities on the way!

New York TO Chicago Road Trip

New York City to Chicago Road Trip Itinerary:

• New York City
• Philadelphia
• Washington D.C

You can also head to Chicago via Finger Lakes & Niagara Falls which is a great option!

See:  New York City to Niagara falls Road trip!

Interactive Map (New York to Chicago Road Trip):

Dive into our Interactive map below!

User Guide:   Simply Click the +/- buttons to zoom in & out,  Click on a favourite attraction, and click directions symbol to give you the driving or walking route directly there!

(Many visitors choose to share our map on facebook by clicking the link below:

[social_warfare]

Webmasters:  Why not embed this map on your website to help your readers? Feel free by clicking the link in the top right corner.

But remember to credit us at:  townandtourist.com/new-york-chicago-road-trip/

How far is Chicago from New York?

There are  795 miles  between New York & Chicago. Driving direct it would take you  13hr, 7 mins.. .but where is the fun in that!

Road Trips  are about the journey and the amazing places to stop along the way!

Related Read:   Best Time to Visit Chicago

Is it cheaper to fly or drive?

It’s not always cheaper to drive, but in many cases it be less than half the cost of flying to drive and alot more fun!

new york road trip hammock girl

Which is the best method of transport from New York to Chicago?

From the Table below we evaluated which is the best method of transport between New York and Chicago. Now this all depends on personal preference.

However, from the data it’s clear that the  Bus is the cheapest method of transport between New York and Chicago.

So if your a real Backpacker and don’t want to  rent a car  then this is a great option for you. However, there are a couple of negatives against taking the Bus.

There is not as much comfort and space as the train and you can’t stop off as many times as you could in a car!

For more on Public transport to Chicago check out:  New York to Chicago on Public Transport: Is it worth it?

Dive into our helpful comparison table below!

Should I take the train between New York & Chicago?

The Amtrak train takes you up through Connecticut, Massachusetts before traveling along the coast of New York state.

This is a really Scenic train ride and an experience in itself. For more info see:  Ultimate Guide to the USA by Amtrak Trains

Buffalo New York train journey

For our full New York to Chicago Road Trip Itinerary

check out: New York City to Chicago Road Trip: Itinerary/Map

3. Chicago to Iowa: wild west road trip!

A Chicago to Iowa Road Trip is a short but sweet mid america road trip! Along the way you will drive through authentic Americana.  Line of sight you can travel the 236 miles  between Chicago & Iowa in approximately 4 hours! However, we prefer to take the more scenic route to really experience old americana.

freight-house-farmers market. Iowa.

Chicago to Iowa Road Trip Itinerary

Here are our Stops along the way.

• Iowa City, Iowa
• Bonus: Amana Colonies

Interactive map (New York to Chicago Road Trip):

Dive into our Interactive Map below, for the best attractions to see on a road trip between Chicago & Iowa.

User Guide:   Simply Click the +/- buttons to zoom in & out, (Zoom out to see Blowing rock).

Click on a favourite restaurant, and click directions symbol to give you the driving or walking route directly there!

(Many visitors choose to  share our map on facebook  by clicking the link below!)

Be sure to visit Galena!

Galena is a historic small town in northwest Illinois. This little town down is old school Americana at its best! Here you will find a host of 19th century buildings such as the 1826 Dowling House and Hourseshoe Mount which offers views of THREE STATES!

You can check out other ancient ceremonial sites at Casper Bluff.

Things to do in Galena:

• Home of Ulysses S Grant
• Chicago Atheneum
• The Dowling House
• Galena Grant Park
• Galena Ghost Tours.
• Galena Trolley Tours

For the full Itinerary be sure to check out this post here:  Chicago to Iowa Road Trip: Wicked Mid West!

2. Atlanta to Chicago Road Trip

Atlanta is known for it’s southern hospitality, diverse musical heritage and number of world records!

It also has the busiest passenger airport in the United States of America the  Harts-field Jackson Atlanta International Airport , which draws over 50 million people annually!

This makes it a popular starting point for many great US road trips!

Atlanta to Chicago Road Trip Itinerary:

• Atlanta, Georgia
• Chattanooga, TN
• Nashville, TN
• Louisville, Kentucky
• Indianapolis, Indiana
• Chicago, Illinois

Interactive map (Atlanta to Chicago Road Trip)

Dive into our interactive Map below!

User Guide:  Use the +/- arrows to zoom in an out of the landmarks. Many users choose to  share the post on facebook  and access the map that way.

Tip:  Turn your phone sideways for easier use. Click the directions button top right to be routed to attraction.

Visit the worlds largest drive inn Restaurant!

Be sure to visit this record breaking institution, covering over two acres in Downtown Atlanta,  Varsity  is the worlds largest drive inn Restaurant and can accommodate up to  600 cars outside  and over  800 people inside . The venue is especially popular when Georgia Tech plays at home.

Fun Fact:  Varsity makes over  two miles of Hot Dogs, 5000 fried pies and 300 gallons of Chilli daily!

Varsity worlds largest food drive in

1. Chicago to San Francisco: The Ultimate Road Trip!

San Francisco is know for its diverse cultures from the Chinatown area to its incredible food scene, iconic landmarks (golden gate bridge, Alcatraz prison island) and hipster vibe.

A road trip between Chicago and San Francisco is the ultimate road trip!

Related Read:   15 Best Waterfalls Near Chicago

How far is San Francisco to Chicago?

San Francisco is 2,132 miles from Chicago! Driving direct with no stops it would take you  31 hours!

You will cross 7 states and numerous cities of the USA! From Iowa to Nevada!

Welcome to San Francisco

Chicago to San Francisco Road Trip Itinerary:

Me & a few friends have actually taken this road trip twice! The first time we went the fastest route via Americas mid west! (Route 2).

Visiting places such as Iowa city and Denver, Colorado.

The second time we took a  longer route  but visited some iconic cities such a Las Vegas and LA.

We even got to see the  World Largest Hot Balloon Festival in Albuquerque , New Mexico!

Wonderful Instagrammable Balloon Photos. See:  20 Golden Reasons to go Albuquerque Balloon Festival?

From LA we hopped onto the Pacific coast highway 1 which is one the  25 Most Epic Driving Roads in the U.S.A: Road Trip Ideas!

Route 1 - Las Vegas & LA Road Trip Itinerary:

• Chicago, IL
• St Louis, MO
• Oklahoma City, OK
• Albuquerque , New Mexico
• Las Vegas , NV
• Los Angeles , CA
• San Jose , CA
• San Francisco , CA

Las-Vegas-Road Trip

Route 2 - Mid West Road Trip Itinerary:

• Iowa city , IA
• Kansas  City, KA
• Denver , CO
• Salt Lake City, UT
• Sacramento, CA

Winter Camping at Grand Sand Dunes Colorado is a incredible experience. Source: theknow.denverpost.com

For more info check out:  20 Incredible Winter Camping Destinations: USA

Interactive Map (Chicago to San Francisco Road Trip):

(The Road Trip Map outlines the two different routes mentioned above)

Route 1: Via St Louis, Albuquerque, Las Vegas and Los Angeles

Route 2: Via Iowa City, Denver, Salt Lake City and Reno.

Related Read:   25 Best Hiking Trails Near Chicago

Should I take the California Zephyr?

The California Zephyr Amtrak train first hit the rails in was 1949. Since then it has taken rail enthusiasts on one of the most scenic train rides in the USA! Which runs between Chicago & San Francisco.

The Scenery on the California Zephyr is world renowned.  On this journey you will cross the farmlands of Nebraska, the  Colorado  Rockies, through the Sierra Nevada mountains before arriving at  San Francisco .

California Zephyr train

The Dome Car:

The Dome Car offers seats facing out of the windows offering panoramic views of the scenery.

The Dome cars are common on scenic routes but do fill up quickly, especially on trains like the California Zephyr which passes through the untouched areas of the Colorado Rockies. So get to the carriage early to avoid disappointment.

Related Read:   15 BEST Boozy Bottomless Brunch in Chicago

Insider Tip:

Listen out for the Commentary of the most significant section of the California Zephyr route and try some classic american eggs and Bacon for breakfast in the diner carriage.

For our full guide check out our Ultimate Guide to the  California Zephyr: Chicago to San Francisco

Where to Stay in San Francisco?

For a recommended list of my favourite places to stay in San Franscisco, follow the link  HERE.

Vital Road Trip Tips:

• Make sure you have all your  Travel Essentials
• Make sure you have all your  Travel Accessories
• Bring a  Great Travel Camera  to capture some scenic shots.

Make sure you are equip with some great Photography Gear!

• Bring some High Quality Hiking boots: See Recommended  Hiking Gear
• Check our recommended  Camping Gear
• Avoid gigantic $15,000 Medical Bills see:  Why you NEED Travel Insurance in 2020?
• Make sure your Car is serviced, with a spare tire or alternatively rent a fully reliable car.

How to get the best car rental Deals?

Check out:  Ultimate Car Rental Travel Hacks!

For RV Rentals we always use:  RV Share

Bring your RV to Tiden Park.

73 Basic Dutch Phrases for Your Next Trip to Netherlands 🇳🇱

Learn essential Dutch phrases for a smooth trip to the Netherlands. Perfect for travelers looking to connect with locals and enrich their experience.

Win a $500 Flight!

Embark on the adventure of a lifetime! Enter our Dream Journey Sweepstakes for a chance to win a $500 travel voucher, redeemable with any major US airline. Whether it's sandy beaches, bustling cities, or tranquil mountains, your dream destination is just an email away!*

Is Sun Country Airlines Safe? Discover How They Prioritize Your Safety

When you're planning your next getaway, the safety of your chosen airline is probably at the top of your list. You've likely heard of Sun Country Airlines, a budget-friendly option that's been gaining popularity. But the big question on your mind is, "Is Sun Country Airlines safe?"

Is Delta Air Lines Safe? Unveiling the Truth for Nervous Flyers

When you're planning your next trip, safety is likely at the top of your list. And if Delta Air Lines is on your radar, you're probably wondering just how safe it is to fly with them. Let's face it, in today's world, the safety of an airline can make or break your travel plans.

Is American Airlines Safe? Uncovering the Truth for Nervous Flyers

When you're planning your next trip, safety is probably at the top of your mind. And if you're considering flying with American Airlines, you're likely wondering just how safe it really is. It's a valid concern—after all, you're cruising at 35,000 feet!

Is Biman Bangladesh Airlines Safe? Unveiling the Truth for Anxious Flyers

When you're planning a trip, especially one that takes you across borders, the safety of your chosen airline is a top priority. You've probably come across Biman Bangladesh Airlines in your search for flights, and it's natural to wonder about its safety record. After all, you're entrusting them with your most precious cargo: you and your loved ones.

Is Arkia Israeli Airlines Safe? Unveiling the Truth That Every Traveler Must Know

When planning a trip, you're likely to ponder over which airline to choose, especially when it comes to safety. If you've got your eyes set on Israel, Arkia Israeli Airlines might have popped up in your search. It's Israel's second-largest airline, but how does it stack up in terms of safety?

Is Air Albania Safe? Unveiling the Truth About Your Next Flight's Security

When planning your next trip, you might wonder about the safety of your chosen airline. It's a valid concern, especially if you're considering flying with a relatively new player like Air Albania. Founded in 2018, it's the flag carrier of Albania, but how does it stack up in terms of safety?

Is Jeju Air Safe? Unveiling the Truth Behind Your Flight Fears

When planning a trip, especially by air, safety is always at the top of your mind. You've probably come across Jeju Air, a popular low-cost carrier in South Korea, and wondered, "Is Jeju Air safe?" It's a valid question, considering the budget-friendly tickets and the airline's growing network across Asia.

Is Air Tahiti Nui Safe? Unveiling What Every Traveler Needs to Know

When planning a trip to the enchanting islands of Tahiti, you're likely considering Air Tahiti Nui for your journey. It's the flagship carrier that promises an exotic travel experience, whisking you away to paradise. But amidst the excitement, a crucial question pops up: Is Air Tahiti Nui safe?

Is Avelo Airlines Safe? Unveiling the Truth for Anxious Flyers

When you're planning your next trip, safety is always at the top of your mind, right? You're probably wondering if Avelo Airlines, the new kid on the block in the aviation world, ticks all the boxes for a safe journey. It's a valid question, especially with so many options out there.

Is PenAir Safe? Unveiling the Truth for Nervous and Aspiring Travelers

When you're planning your next flight, safety is probably at the top of your list. You've likely come across PenAir in your search for regional flights, but you're wondering: is PenAir safe? It's a valid question, especially when flying to some of the more remote locations PenAir serves.

Is Ravn Alaska Safe? Unveiling Truths Behind Your Flight's Reliability

When planning a trip to the Last Frontier, you might wonder about the best way to hop between its vast landscapes. Ravn Alaska pops up as a popular option, but there's a big question on your mind: Is Ravn Alaska safe? Let's dive into what makes an airline tick in terms of safety and see how Ravn stacks up.

Is Breeze Airways Safe? Unveiling the Truth for Anxious & Aspiring Travelers

When you're eyeing those tempting deals from Breeze Airways for your next trip, it's only natural to wonder about their safety record. After all, who doesn't want a smooth and secure journey to their dream destination? Breeze Airways, a newcomer in the sky, has sparked curiosity among travelers seeking both value and peace of mind.

Is Cape Air Safe? Unveiling the Truth Behind Pilot Training and Fleet Safety

When planning your next adventure or business trip, you're likely to ponder over the safety of your chosen airline. If Cape Air's on your radar, you're probably asking, "Is Cape Air safe?" It's a valid question that deserves a closer look, especially when your comfort and peace of mind are at stake.

Is Silver Airways Safe? Unveiling the Truth for Anxious Flyers

When planning your next trip, you're likely juggling a lot of decisions. Where to stay, what to pack, and, crucially, which airline to trust with your safety in the skies. If you're considering Silver Airways for your journey, you might be wondering just how safe it is. After all, flying can be nerve-wracking enough without worrying about the reliability of your chosen airline.

Is GoJet Airlines Safe? The Truth Behind Passenger Reviews and Safety Concerns

When you're planning your next trip and considering flying with GoJet Airlines, one question might pop into your mind: "Is GoJet Airlines safe?" It's a valid concern, especially in today's world where safety is paramount. Let's dive into what makes an airline safe and see how GoJet stacks up.

Is Endeavor Air Safe? Unveiling the Truth Behind Your Secure Journey

When you're planning your next trip and considering flying with Endeavor Air, it's natural to wonder about safety. After all, you want your journey to be as smooth and worry-free as possible. Safety is a top priority for any airline, but how does Endeavor Air stack up?

Is Trans States Airlines Safe? Unveiling the Truth Behind Pilot Training & Safety

When you're planning your next trip and considering flying with Trans States Airlines, it's natural to wonder about their safety record. After all, ensuring a safe journey is at the top of everyone's list. You're not alone in your curiosity, and the good news is, we've got the scoop for you.

Is Air Wisconsin Safe? Unveiling the Truth Behind Your Flight's Safety

When you're planning your next trip and considering flying with Air Wisconsin, safety is likely one of your top concerns. It's a big deal choosing an airline, especially with the myriad of options and opinions floating around.

Is Envoy Air Safe? Unveiling the Truth Behind Your Next Flight

When you're planning your next trip and considering flying with Envoy Air, it's natural to wonder about the airline's safety record. After all, your safety is paramount, and you want to ensure you're making the best choice for your travel.

Is Mesa Airlines Safe? Discover What Passengers Aren't Telling You

When you're planning your next trip and considering flying with Mesa Airlines, safety is likely at the top of your mind. It's a big world out there, and knowing you're in good hands while jetting off to your next adventure can make all the difference.

Is Compass Airlines Safe? Uncovering What Every Traveler Must Know

When you're planning your next trip and considering flying with Compass Airlines, it's natural to wonder about their safety record. After all, ensuring a safe journey is at the top of everyone's list. But diving into the world of airline safety can feel like navigating through a maze. Don't worry; we've got you covered.

Is Republic Airways Safe? Insights That Every Nervous Flyer Must Read

When you're planning your next trip and considering flying with Republic Airways, it's natural to wonder about their safety record. After all, ensuring you're in good hands while thousands of feet up in the air is pretty crucial. You're not alone in your concerns; it's a question on the minds of many travelers.

Is SkyWest Airlines Safe? Unveiling the Truth That Every Traveler Must Know

When planning your next trip, you might be wondering about the best airline options out there. Safety, no doubt, tops your list of concerns. You've probably heard of SkyWest Airlines, a major player in the regional airline sector. But the burning question remains: Is SkyWest Airlines safe?

Is Icelandair Safe? Discover Why Flyers Trust Their Journey With Us

When you're planning a trip that involves flying, safety naturally tops your list of concerns. And if Iceland's stunning landscapes are calling your name, you're probably considering Icelandair for your journey. But how safe is this airline, really?

Is Luxair Safe? Unveiling What Really Matters to Nervous Flyers

When planning your next trip, you're likely scrolling through countless options, wondering which airline will get you there safely and comfortably. Luxair, Luxembourg's flag carrier, often pops up as a top choice for European destinations. But in the sea of airlines, you might ask yourself, "Is Luxair safe?"

Is SpiceJet Safe? Uncovering the Truth Behind Passenger Reviews

When you're planning your next trip, safety is always at the top of your mind. And if you're considering flying with SpiceJet, you might be wondering just how safe it is. After all, flying can be daunting, and choosing the right airline is crucial for a worry-free journey.

Is El Al Safe? Debunking Myths & Unveiling the Truth for Nervous Flyers

When you're planning a trip, especially an international one, safety is likely at the top of your list. And if your travels are taking you to or from Israel, you've probably heard of El Al. It's Israel's national airline and has a reputation that precedes it. But what's behind the buzz? Is El Al really as safe as they say?

Is China Eastern Safe? Unveiling the Truth Behind Your Flight Fears

When you're planning a trip, especially one that spans continents, safety is likely at the top of your list. You've probably come across China Eastern Airlines in your search for flights, and it's natural to wonder about their safety record. After all, you're entrusting them with your most precious cargo - yourself and your loved ones.

Is China Southern Safe? Unveiling the Truth Behind Your Flight Concerns

When it comes to air travel, safety is always at the forefront of everyone's mind. You might be planning your next trip and wondering, "Is China Southern safe?" It's a valid question, especially when venturing far from home.

Is Malaysia Airlines Safe? Unveiling the Truth for Anxious Travelers

When you're planning your next adventure or business trip, the airline you choose is a big deal. You want comfort, good service, and most importantly, safety. Malaysia Airlines often pops up as a tempting option with its attractive routes and competitive prices. But there's that nagging question in the back of your mind: Is Malaysia Airlines safe?

Is Japan Airlines Safe? Unveiling the Truth for Anxious Flyers

When planning your next trip, safety is likely at the top of your list, especially when it comes to choosing an airline. You might be wondering, "Is Japan Airlines safe?" Well, you're in the right place to find out. Japan Airlines, known for its impeccable service, also prides itself on its safety record.

Is ANA Safe? Discover How They Ensure Your Peace of Mind in the Skies

When you're planning a trip, especially one that involves flying, safety is likely at the top of your mind. You might be wondering about All Nippon Airways, commonly known as ANA, and its safety record. Is it a reliable choice for your next journey?

Is Singapore Airlines Safe? Unveiling the Secrets Behind Their Flawless Safety Record

When you're jetting off to exotic locales or crucial business meetings, the last thing you want to worry about is your safety in the sky. That's where Singapore Airlines comes into play. Known for its impeccable service, it's natural to wonder about its safety record too.

Is Emirates Safe? Unveiling What Happy Travelers Really Think

When you're planning your next journey, safety is likely at the top of your list. You've probably heard a lot about Emirates, known for its luxurious experience, but how does it stack up in terms of safety? Let's dive into what makes an airline safe and see where Emirates lands.

Is LOT Safe? Unveiling the Truth Behind Your Flight's Safety

When you're planning a trip, the safety of the airline you choose is a top priority. You might've heard about LOT Polish Airlines and wondered, "Is LOT safe?" Well, you're not alone in asking. Safety concerns are valid, especially when it's about flying thousands of feet above the ground.

Is Aeromexico Safe? Unveiling What Every Traveler Needs to Know

When you're planning your next trip and considering flying with Aeromexico, safety might be at the top of your mind. It's natural to wonder about the safety records of airlines these days, especially with the amount of travel we all do. Aeromexico, as one of the leading carriers in Latin America, often comes under scrutiny.

Is Norwegian Safe? Discover Why Travelers Trust Its Skies

When you're planning your next adventure, safety is always at the top of your list. And if Norway's on your radar, you're probably wondering, "Is Norwegian safe?" Let's dive into what makes this Nordic country a destination worth considering from a safety perspective.

Is Allegiant Air Safe? Unveiling the Truth About Your Flight's Safety

When you're planning a trip, the safety of the airline you choose is a top priority. You've probably heard mixed reviews about budget airlines, and Allegiant Air often comes up in those conversations. It's natural to wonder, "Is Allegiant Air safe?"

Is Hawaiian Airlines Safe? Discover Why Flyers Trust This Paradise Airline

When you're planning a tropical getaway, the last thing you want to stress over is whether your flight will be a smooth sail or a turbulent ride. Enter Hawaiian Airlines, a name that's almost synonymous with the aloha spirit and island hopping. But beyond the lei greetings and in-flight POG juice, you're probably wondering, "Is Hawaiian Airlines safe?"

Is Frontier Airlines Safe? Unveiling the Truth Behind Your Flight Fears

When you're planning your next adventure or business trip, the airline you choose can make all the difference. You've probably heard about Frontier Airlines, known for its budget-friendly fares, but you might be wondering, "Is Frontier Airlines safe?" It's a valid question that deserves a closer look, especially in today's travel climate.

Is Spirit Airlines Safe? Unveiling the Truth Behind Your Flight Fears

When you're planning a trip and looking for budget-friendly options, Spirit Airlines often pops up as a tempting choice. But amidst the excitement of snagging a great deal, you might pause and wonder, "Is Spirit Airlines safe?" It's a valid question, especially when you're about to trust them with your most precious cargo—yourself!

Is JetBlue Safe? Uncovering the Truth Behind Their Safety Measures

When you're planning your next trip, the airline you choose is as crucial as your destination. You've probably heard a lot about JetBlue, known for its comfy seats and ample legroom, but how does it stack up in terms of safety? It's a question worth asking, especially in today's travel climate.

Is Alaska Airlines Safe? Discover Why Flyers Trust Their Journey With Them

When you're planning your next trip, safety is likely at the top of your list. You're not just looking for a smooth flight; you want peace of mind from takeoff to touchdown. That's where Alaska Airlines comes into play. It's a name you've probably heard tossed around when talking about reliable air travel, but how safe is it really?

Is Southwest Airlines Safe? Uncovering What Every Traveler Needs to Know

When you're planning your next trip, safety is always at the top of your mind. And if you're considering flying with Southwest Airlines, you might be wondering just how safe your journey will be. It's a valid concern, especially in today's world where travel safety has become more important than ever.

Is United Airlines Safe? Real Passengers Share Their Experiences

When you're planning your next trip, safety is probably at the top of your list, especially when it comes to choosing an airline. You've likely come across United Airlines, a major player in the aviation industry, and wondered, "Is United Airlines safe?" It's a valid question that deserves a closer look.

Ultimate Guide: Best Places to Live in Hawaii for Every Lifestyle

Dreaming of living in paradise? Hawaii's got you covered, with its stunning beaches, lush landscapes, and Aloha spirit. But with so many amazing spots, deciding where to plant your roots can be tough.

Ultimate Guide: Top Places to Live in Florida for Everyone - Beaches, Festivals & More

Thinking about moving to Florida? You're not alone! The Sunshine State is famous for its gorgeous beaches, vibrant cities, and laid-back lifestyle. But with so many great places to choose from, deciding where to plant your roots can be tough.

Ultimate Guide: Top Family-Friendly Spots in NC - From Asheville to Outer Banks

Looking for the perfect spot in North Carolina to plant your family roots? You're in luck! This state's got a little something for everyone, from bustling cities to quiet, leafy suburbs.

Top Places to Thrive in Your 20s: A Guide to Affordability, Adventure, & Opportunities

Ah, your 20s! A time to explore, grow, and maybe even settle down in a new spot that feels just right. It's all about finding that perfect blend of fun, opportunity, and affordability.

Ultimate Guide: Best Places to Live in Houston for Everyone - From Retirees to Families

Houston's a big city, with even bigger opportunities for finding the perfect spot to call home. Whether you're all about the hustle and bustle of city life or looking for a quiet corner to settle down, there's something here for everyone.

Ultimate Guide: Best Places to Live in Missouri for Everyone - From Retirees to Young Adults

Thinking about moving to Missouri or just curious about the best spots to call home in the Show-Me State? You're in luck. Missouri's got a little something for everyone, from bustling city vibes to quiet, leafy suburbs.

Ultimate Guide: Top Places to Live in Connecticut for Every Lifestyle

Thinking about making a move to Connecticut? You're in for a treat! This state's got a little bit of everything – from cozy small towns to bustling cities. It's all about finding the spot that feels just right for you.

Ultimate Guide: Best Places to Live in Indiana for Everyone - Schools, Costs & Lifestyle

Thinking about calling Indiana home? You're in for a treat! The Hoosier State is packed with charming towns, bustling cities, and everything in between. Whether you're after the quiet of the countryside or the buzz of city life, Indiana's got you covered.

Ultimate Guide: Top Places to Live in Illinois for Everyone - Families to Retirees

Thinking about making a move to Illinois? You're in for a treat! The Prairie State is not just about deep-dish pizza and the Windy City. There's a lot more to discover, from cozy small towns to bustling suburbs that offer the best of both worlds.

Ultimate Guide: Top East Coast Havens for Every Lifestyle & Age

Dreaming of waking up to the sound of waves or perhaps craving the vibrant city vibes only the East Coast can offer? You're in luck because we're diving into the best spots that just might make you want to pack your bags today. From quaint towns with rich history to bustling cities with endless opportunities, the East Coast has something for everyone.

Ultimate Guide: Top Places to Live Near Nashville for Every Lifestyle

Thinking about moving close to the heart of country music? Nashville's got more than just tunes to offer. It's surrounded by some pretty sweet spots that give you the best of both worlds: serene living and easy access to the city vibes.

Ultimate Guide: Best Places to Live in New Mexico for Every Lifestyle

Thinking about making a move to New Mexico? You're in for a treat! With its rich culture, stunning landscapes, and sunny weather, it's no wonder you're considering it. But with so many awesome places to choose from, where should you start?

Ultimate Guide: Top Places to Live in New Hampshire for Every Lifestyle

Thinking about making a move to New Hampshire? You're in for a treat! From the stunning White Mountains to the serene lakes, there's a spot for everyone in this charming New England state. Whether you're after the hustle and bustle of city life or the peacefulness of the countryside, New Hampshire offers a unique blend of both.

Ultimate Guide: Best Places to Live in Delaware for Everyone [2024]

Thinking about making Delaware your new home? You're in luck! This little gem of a state might be small, but it's packed with some of the best places to live on the East Coast. From cozy beach towns to bustling city life, Delaware's got a spot for everyone.

Ultimate Guide: Top Places to Live in Massachusetts for Everyone

Thinking about making a move to Massachusetts? You're in for a treat. This state's got a little bit of everything, from bustling cities to quiet, quaint towns. Whether you're after top-notch schools, vibrant cultural scenes, or just some stunning nature, Massachusetts delivers.

Ultimate Guide: Best Places to Live in Minnesota for All Lifestyles

Thinking about making a move to Minnesota, or just curious about the best spots to call home in the Land of 10,000 Lakes? Well, you're in luck. Minnesota's not just about the cold and snow; it's packed with cities that boast great jobs, vibrant communities, and plenty of outdoor fun.

Ultimate Guide: Best Places to Live in Alaska for Everyone - From Retirees to Families

Thinking about making the big move to Alaska? You're in for a treat! It's not just about snow and sled dogs; Alaska's got some of the most stunning landscapes and tight-knit communities you'll find anywhere.

Ultimate Guide: Top Places to Live in West Virginia for Every Lifestyle

Thinking about calling West Virginia home? You're in for a treat. This place isn't just about stunning mountains and rivers; it's got some hidden gems where life feels just right. Whether you're after that small-town charm, vibrant city vibes, or a quiet spot surrounded by nature, West Virginia's got a spot for you.

Ultimate Guide: Best Places in Florida for Families - Live Happily Ever After

Thinking about moving your family to Florida? You're not alone! The Sunshine State is famous for its warm weather, beautiful beaches, and family-friendly communities. But with so many options, deciding where to plant your roots can be a bit overwhelming.

Ultimate Guide: Top Places in North Carolina for Retirees & More

North Carolina's got a charm that's hard to beat, especially if you're looking to enjoy your retirement to the fullest. From the cozy mountains to the sunny beaches, there's a spot for every retiree to call home.

Ultimate Guide: Best Affordable NJ Spots Near NYC for Every Lifestyle

Living close to NYC is a dream for many, but let's be real, it can get pricey. Good news, though! New Jersey offers some gems that won't break the bank and still keep you close to the Big Apple. Whether you're after the bustling streets or a quiet corner, there's a spot for you.

Ultimate Guide: Top Vermont Havens for Everyone - From Retirees to Young Families

Thinking about making a move to Vermont? You're not alone. This charming state, known for its stunning landscapes and cozy small towns, is a magnet for those seeking a quieter, more scenic life. With its mix of vibrant communities and peaceful countryside, Vermont offers the best of both worlds.

Ultimate Guide: Best Places to Live in Arkansas for Everyone (2024)

Thinking about making a move to the Natural State? You're in for a treat! Arkansas is known for its stunning natural beauty, friendly folks, and a cost of living that's hard to beat. Whether you're drawn to the hustle and bustle of city life or the peace and quiet of the countryside, Arkansas has got something for everyone.

Idaho's Top Living Spots: The Ultimate Guide for Everyone - From Retirees to Families

Thinking about moving to Idaho? You're not alone. With its stunning landscapes and friendly communities, it's no wonder more and more people are calling it home. But with so many great spots, it can be tough to decide where to plant your roots.

Ultimate Guide: Best Places to Live in Wyoming for Everyone

Thinking about making a move to Wyoming? You're in for a treat! This state's known for its wide-open spaces, stunning scenery, and a lifestyle that's both laid-back and adventurous. Whether you're drawn by the call of the wild or the promise of a peaceful, community-focused life, Wyoming's got a spot for you.

Ultimate Guide: Top Spots in South Carolina for Young Adults - Live, Work & Play

South Carolina's charm isn't just in its sweet tea and beaches. For young adults looking for a fresh start or a new scene, it's got some hidden gems that might just be your next home sweet home. From bustling cities to cozy coastal towns, there's a spot for every vibe and ambition.

Ultimate Guide: Best Places to Live in Washington State for Everyone

Thinking about making a move to the Evergreen State? You're in for a treat! Washington's got a bit of everything, from bustling city life to quiet, cozy towns. Whether you're after the techy vibes of Seattle or the serene landscapes of the Olympic Peninsula, there's a spot just for you.

Ultimate Guide: Top Places to Live in Montana for Everyone – From Retirees to Families

Thinking about calling Montana home? You're not alone. With its breathtaking landscapes and wide-open spaces, it's a place that calls to the heart of adventurers and peace-seekers alike. But with so many amazing spots, picking the best place to plant roots can feel overwhelming.

Ultimate Guide: Best Places to Live in Virginia for Every Lifestyle

Thinking about making a move to Virginia? You're in for a treat! This state's got everything from bustling cities to quiet, cozy towns. Whether you're after top-notch schools, job opportunities, or just a beautiful place to call home, Virginia's got you covered.

Ultimate Guide: Top Places to Live in North Carolina for Happiness, Weather & More

Thinking about making a move to North Carolina? You're in for a treat! From the bustling streets of Charlotte to the serene beaches of the Outer Banks, North Carolina's got a little something for everyone. Whether you're after the hustle and bustle of city life or the quiet charm of small-town living, you'll find your perfect spot here.

Ultimate Guide: The Best Places to Live in Georgia for Everyone—from Retirees to Families

Thinking about making a move to Georgia? You're not alone. With its warm climate, rich culture, and booming job market, it's no wonder people are flocking to the Peach State. But with so many great places to choose from, where do you even start?

Ultimate Guide: Best Places to Live in Florida for Every Lifestyle

Thinking about moving to Florida? You're not alone! The Sunshine State is a magnet for folks seeking sunshine, beaches, and that laid-back lifestyle. But with so many awesome spots, picking the best place to plant your roots can feel overwhelming.

Ultimate Guide: Best Places to Live in Indianapolis for Everyone

Thinking about moving to Indianapolis? Great choice! Indy's got a lot to offer, from vibrant neighborhoods to bustling city life. But with so many spots to choose from, finding the perfect place to call home can feel like looking for a needle in a haystack.

Ultimate Guide: Best Places to Live in Orlando for Families & More

Orlando's not just about theme parks and tourist spots; it's a fantastic place to plant roots, especially if you've got a family in tow. With its sunny weather, great schools, and endless activities, it's no wonder families flock here. But with so many neighborhoods, choosing where to live can feel like finding a needle in a haystack.

Ultimate Guide: Top Places in Oregon for Young Adults - Live, Play, Thrive

Oregon's got a vibe that's hard to beat, especially if you're a young adult looking for the perfect spot to plant your roots. With its mix of bustling cities, laid-back towns, and everything in between, there's a place for every taste and lifestyle.

Ultimate Guide: Top Places to Live in Columbus Ohio for Every Lifestyle

Looking for the perfect spot to call home in Columbus, Ohio? You're in luck! Columbus is a city brimming with charm, diverse communities, and endless opportunities. Whether you're all about the nightlife, a fan of quiet suburbs, or somewhere in between, there's a place just for you.

Ultimate Guide: Top Affordable Places in North Carolina for Everyone

Thinking about moving to North Carolina but worried about the cost? You're in luck! North Carolina's got some hidden gems where you can enjoy the good life without breaking the bank. From cozy mountain towns to vibrant cities, there's a spot for everyone.

Ultimate Guide: Top East Coast Havens for Everyone - From Retirees to Partygoers

Thinking about making a move to the East Coast? You're in for a treat! From bustling cities to quiet seaside towns, there's a spot for everyone. Whether you're dreaming of fresh seafood by the ocean or a fast-paced city vibe, we've got you covered.

Ultimate Guide: Top Places to Live in Brooklyn for Every Demographic

Brooklyn's got a vibe like nowhere else. It's where the cool kids hang and the artists create. But with so many neighborhoods, picking where to call home can feel like finding a needle in a haystack.

Ultimate Guide: Best Places to Live in San Antonio for All Lifestyles

San Antonio's got a vibe that's hard to beat, with its rich history, vibrant culture, and killer food scene. If you're thinking about making the move or just curious, you're in the right spot. Finding the perfect neighborhood in this sprawling city can be a bit like searching for a needle in a haystack—but a whole lot more fun.

Ultimate Guide: Best Places to Live in Kentucky for Everyone

Thinking about calling Kentucky home? You're onto something special. Known for its rolling hills, horse farms, and friendly communities, the Bluegrass State offers a unique blend of natural beauty and welcoming neighborhoods.

Ultimate Guide: Top Places to Live in Maryland for Everyone's Wish List

Thinking about moving to Maryland? You're in for a treat! This state's got a mix of everything - from bustling city vibes in Baltimore to the laid-back, scenic beauty of its coastal towns.

Ultimate Guide: Best Places to Live in Portland for Every Lifestyle

Thinking about making Portland your new home? You're in for a treat! This city's got a vibe like no other, with its quirky culture, amazing food, and stunning nature spots. But with so many cool neighborhoods, picking the perfect spot can be a bit of a head-scratcher.

Ultimate Guide: Top Austin Neighborhoods for Every Lifestyle & Budget

Thinking about making a move to Austin? You're not alone. This vibrant city has been pulling folks in with its unique charm, incredible music scene, and mouth-watering BBQ. But with so many cool neighborhoods, picking the right spot can feel like finding a needle in a haystack.

Ultimate Guide: Best Places to Live on East Coast for Everyone – From Retirees to Families

Dreaming about moving to the East Coast? You're not alone. With its charming towns, bustling cities, and stunning beaches, the East Coast offers a little something for everyone. Whether you're after the vibrant city life or a quiet seaside retreat, you'll find your perfect spot here.

Ultimate Guide: Top Places to Live in Washington DC for Every Lifestyle

So, you're thinking about moving to Washington, DC? Great choice! The city's not just about politics and monuments. It's got neighborhoods that'll make you wanna stay forever. From trendy spots buzzing with cafes and galleries to quiet, leafy streets perfect for Sunday strolls, DC's got a bit of everything.

Ultimate Guide: Best Affordable Places to Live in North Carolina for Every Lifestyle

Looking for a spot in North Carolina that's easy on your wallet but still ticks all the boxes for a great place to live? You're in luck. North Carolina's got a bunch of hidden gems that offer a fantastic quality of life without breaking the bank.

Ultimate Guide: Top Family-Friendly California Locales for Every Lifestyle

California's got it all for families looking for their next home sweet home. From the sunny beaches to the scenic mountains and bustling cities, there's a spot for every family's taste and budget.

Ultimate Guide: Top Places to Live in the Midwest for Every Lifestyle

Thinking about calling the Midwest home? You're in for a treat! This heartland is chock-full of hidden gems, each offering its unique blend of charm, community, and comfort. From bustling cities with all the modern amenities to quiet towns where everyone knows your name, there's a perfect spot for everyone.

Ultimate Guide: Best Places to Live in Georgia for Every Lifestyle

Looking for the perfect spot in Georgia to call home? You're in luck! Georgia's got a little bit of everything, from bustling city vibes in Atlanta to the laid-back coastal charm of Savannah. It's a place where you can find your niche, whether you're after top-notch schools, thriving job markets, or just a great community feel.

Ultimate Guide: Top Places to Live Near Orlando for Every Lifestyle

Looking to move close to Orlando but not sure where to start? You're in luck! Orlando's surrounding areas offer a mix of vibrant communities, each with its own unique charm. Whether you're after the buzz of city life or the tranquility of suburbia, there's a spot near Orlando that's perfect for you.

Ultimate Long Island Living Guide: Top Spots for Everyone's Lifestyle

Dreaming of a spot with sandy beaches, cozy neighborhoods, and endless bagels? Long Island's got you covered. It's not just about the stunning coastline; this place is a melting pot of cultures, cuisines, and communities. Whether you're a city escapee, a nature lover, or somewhere in between, there's a perfect corner here for you.

Ultimate Guide: Best Places to Live in Arizona for Young Adults - Explore, Thrive, & Enjoy

Thinking about making a move to Arizona? You're not alone. With its stunning landscapes, booming job market, and vibrant culture, it's no wonder young adults are flocking to the Grand Canyon State. But with so many cool spots to choose from, where should you set up camp?

Ultimate Guide: Best Affordable Places in Washington State for Everyone

Looking for a spot in Washington State that won't break the bank? You're in luck! We've got the scoop on the best affordable places that still offer that amazing Pacific Northwest vibe. Whether you're dreaming of cozy mountain towns or vibrant city life, Washington's got a little something for everyone.

Ultimate Guide to Arizona: Top Spots for Young Adults – Live, Play, Thrive

Looking for the perfect spot in Arizona to plant your roots as a young adult? You're in luck! The Grand Canyon State isn't just about breathtaking landscapes and sunsets that'll blow your mind. It's also home to some pretty awesome places that cater specifically to the younger crowd.

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