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The 14 best road trips from Chicago

Need a change of scenery? Load up the car and hit the road on one of the best road trips from Chicago

No coast? No problem. Summer is approaching, and it's the perfect time to embark on a scenic road trip from Chicago to transport yourself to somewhere  completely different. Whether you prefer sipping bourbon in Louisville, hiking in Eau Claire or sunbathing in Door County, there's a perfect mini-vacation here for everyone. So if you're not sure where to start when it comes to a Midwestern trip, we recommend you load up the car and hit the road—one of these road trips from Chicago could quickly turn into your favorite weekend getaway . 

RECOMMENDED: The best day trips from Chicago

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Best road trips from Chicago

1.  St Louis, MO

Driving time from Chicago: 4 hrs 30 min

While beer, blues and BBQ are likely on the top of your St Louis bucket list (and rightfuly so), there's a lot more to discover in the Gateway to the West—like custard from Ted Drewes and a walk around Forest Park. There's also a ton to see on the five-hour drive from Chicago: Stop off at Wilmington, IL to see a roadside attractions called the Gemini Giant, or in Atlanta, IL to take a photo with Paul Bunyon holding a massive hotdog. 

Discover the best things to do in St Louis

2.  Eau Claire, WI

Driving time from Chicago: 5 hrs

Folks head to the Chippewa Valley in northern Wisconsin for its rolling hills and colorful foliage (plus plenty of beer and cheese to smuggle back to Chicago), but there are some worthy sights along the road as well. Snap a selfie with Pinkie the Elephant in Deforest, WI and sample cranberry-flavored everything at the Wisconsin Cranberry Discovery Center   in Warrens, WI. Once you're in Eau Claire, trade in the car for a kayak:  Riverside Bike & Skate   in downtown Eau Claire rents canoes and kayaks and has shuttles that will drive you upstream so you can hit the Chippewa River. 

3.  Traverse City, MI

The charming resort town of Traverse City, located at Michigan’s northern tip, offers plenty to do for nature enthusiasts. Clinch Park and Bryant Park have gorgeous, popular beaches while the more remote Haserot and North Bar Lake beaches offer the chance for a secluded getaway. You’re also within a stones throw of the coastal M-22, one of the most scenic drives in America, as well photo-ops at the Grand Traverse and Little Sable lighthouses. 

Discover the best things to do in Traverse City

4.  Cincinnati, OH

Driving time from Chicago: 5 hrs 

If Skyline Chili is not your bag, don’t worry—there’s a whole lot more to the Queen City than its most famous tourist foodstuff. Cincy has been undergoing a major glow-up over the past decade or so, from the ever-evolving Smale Riverfront Park, which offers lots to do and gorgeous views of the skyline and the Ohio River to the revitalization of the historic Over-the-Rhine neighborhood. There, you'll find a number of must-visit spots, including the popular Rhinegeist Brewery, the vibrant Findlay Market , the stunning Music Hall and Washington Park , which sports a sweet playground and community events throughout the year. Plus, the Cincinnati Zoo is one of the best in the country, and the only place you can see Internet icon Fiona the Hippo in person. That in itself is worth the trip.

5.  Shawnee Hills Wine Trail, IL

Driving time from Chicago: 6 hrs

Not going to make it to Napa this year? Opt for the just-as-beautiful Shawnee Hills Wine Trail instead. The 3 5-mile scenic drive meanders through Shawnee National Forest in southern Illinois and features  11 award-winning wineries in cute towns like Cobden, Alto Pass, and Pomona. If you need more than wine to prompt a trip, there's plenty of nature in the vicinity and the nearby town of Murphysboro is home to some of the finest BBQ in the Midwest at 17th Street Barbecue . 

6.  Bloomington, IN

Driving time from Chicago: 4 hrs

This cozy college town offers some big-city amenities, but it's the surrounding hills, forests and lakes that make it special. A short itinerary could look like: Hike the Deam Wilderness trails; s ee the Morgan-Monroe State Forest wildflowers; admire the Cedar Bluffs Nature Preserve limestone bluffs; g o fishing at the reservoir lakes. Just don't forget to leave room for a meal at  Feast Market & Cellar , a family-owned kitchen with a lovely corner porch where everything is made from scratch daily. 

7.  Door County, WI

Driving time from Chicago:  4 hrs 30 min

The road trip doesn't end when you reach Door County; There's plenty to navigate by car as you wander the series of small towns located on a beautiful 75-mile peninsula surrounded by Lake Michigan and Green Bay. There are also 53 public beaches, five state parks, and 300 miles of shoreline so get ready to put some miles on your car. Need a pit stop? Milwaukee is a little less than half way. 

8.  Louisville, KY

Kentucky’s largest city, located just across the Ohio River from southern Indiana, is steeped in bourbon and long on charm. The home of the old fashioned and mint julep embraces its role as the gateway to Bourbon Country. The city now has 10 tourable distilleries, including   Evan Williams,   Angel’s Envy   and  Old Forester . If bourbon and honkytonk aren't for you, downtown Louisville has an incredible art scene and is booming with independent businesses and charming shops. 

Discover the best things to do in Louisville

9.  Saugatuck, MI

Driving time from Chicago: 2 hrs 30 min

This dreamy lakeside town (and next-door neighbor Douglas) has long been a favorite of Chicagoans looking to spend time on the water, whether it’s a boat on the Kalamazoo River or a relaxing day on one of the area’s six clean, inviting beaches. Whether it’s hiking the Saugatuck Dunes, window shopping on Butler Street or enjoying dinner and drinks alfresco, there are many ways to get some much-needed fresh air here. It’s also one of the Midwest’s best queer-friendly vacation destinations, home to more than 100 LGBTQ-owned and friendly businesses. 

10.  Toledo, OH

The road from Chicago to Ohio is filled with worthwhile attractions, including Indiana Dunes State Park and the Hall of Heroes Super Hero Museum in Elkhart, Indiana. Once you arrive in Toledo, you'll be greeted with picturesque churches, wild urban parks, a trendy jazz culture and plenty of microbreweries to keep you busy. Just outside the city you'll also find fall-harvest overload in the way of apple and pumpkin farms where you can pick your own fruits and veggies and gorge on baked treats.

11.  Detroit, MI

Despite what Blackhawks fans may chant, there is plenty about Detroit that doesn’t suck. You could easily spend a day or two on art alone, thanks to world-class museums like the Detroit Institute of Arts and the Museum of Contemporary Art Detroit ; powerful, immersive public art like the Heidelberg Project and colorful, whimsical folk art like Hamtramck Disneyland . Enjoy a leisurely morning browsing at at Eastern Market showcasing dozens of artisan food producers, makers and crafters, and then check out the tempting restaurant and bar options nearby. On the way home, stop in neighboring Dearborn, home to the largest and most diverse Arab community in the U.S., for delicious food at spots like Al-Ameer , Sheeba and Shatila Bakery . 

12.  Ann Arbor, MI

Driving time from Chicago: 4 hrs 

If you'd rather stick to less-crowded cities, skip Detroit and opt for Ann Arbor instead. Foodies and beer nerds will love this low-key vacation spot for its pletehora of good restaurants and breweries. Home to the renowned University of Michigan, this city’s quaint downtown is full of unique shops, spots to eat and so much more (make sure Blank Slate Creamery is on your list). 

Discover the best things to do in Ann Arbor

13.  Shipshewana, IN

Driving time from Chicago: 2 hrs

OK, just hear us out. The heart of Indiana Amish country is a great option for a convenient road trip perfect for families, history buffs and, most of all, antiquers. The Shipshewana Trading Place Flea Market is a bargain-hunter’s dream—the largest flea market in the Midwest, with lively auctions Wednesday mornings. After a morning of browsing and bargaining, you’ll work up an appetite for some Amish home cooking, which you can even sample in a literal Amish home . For outdoorsy types, nearby Mongo offers canoe and kayak rentals for a relaxing day on the water. 

14.  Des Moines, IA

There's a surprising amount to explore in a weekend in Des Moines, from more than 20 breweries in the metro area to the six-mile Art Route , which showcases 87 public art pieces from sculptures to murals. But what really makes Des Moines worth visiting are its summer events, like the eclectic 80/35 music festival, and, of course, the festive juggernaut that is the Iowa State Fair , where you can get 69 different food-on-a-stick creations (nice). When you're heading back on I-80, don't miss the World's Largest Truck Stop in Walcott, truly a site to behold.

Need more travel inspiration?

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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…

Do you need a rental car for your road trip? Check out the award-winning comparison site Discover Cars for the BEST DEALS the world over. Book early for the best price!

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

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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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!

There may be affiliate links in this post, which means we may get a small commission if you make a purchase. It’s at no extra cost to you and helps keep TLT free. Everybody wins!

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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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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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

Beautiful Resort with an Indoor Pool

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 with River Views

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

New Modern Budget-Friendly Hotel with Indoor Pool

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

Highly Rated B&B in the Center of the City with a Fabulous Breakfast

Family and Budget-Friendly Hotel with Pool and Free Parking

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

4-Star Beach Inn with Spa right on Lake Erie

Lodge in the heart of Ohio wine country

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

Apartment-style Guesthouse right Downtown

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 right Across from 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 Treehouse Cabin with Private Bathroom and Deck

Historic Mansion with a Free Breakfast and Cool Indoor Lounge

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 2-bedroom Country Cabin with Modern Amenities

1 Bedroom Cabin, sleeps 4 with Outdoor Deck

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: Gingerbread House just steps away 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: Cozy Cabins right by 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: Cool Hotel for Couples

Family-Friendly Hotel with an Outdoor Pool

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: Popular Lodge right on the Branson Strip

New Hotel across from 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 and Spa with Bar and Free Bikes

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!

• About Author
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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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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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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.

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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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Best Road Trips from Chicago

Looking to leave Chicago and hit the road? Fortunately there are many amazing places to visit in the Midwest that you can easily drive to from Chicago whether you love nature, beaches, cities or small towns. Here are the best road trips from Chicago from shorter road trips that you can visit as a day trip from Chicago to longer road trips for a weekend getaway or even a week long vacation.

(And make sure to check out my  essential road trip packing list (with free printable pdf)  and  road trip music playlist  to make sure you have all your road trip essentials before you go!)

Best Road Trips From Chicago

Disclaimer: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you. As an Amazon Associate I earn from qualifying purchases.

Lake Geneva, Wisconsin

Distance from Chicago: 83 miles

Stay: Grand Geneva Resort & Spa

Lake Geneva is a resort city on the shores of Geneva Lake in southeastern Wisconsin. The area is a popular vacation destination for Chicago – wealthy Chicagoans built their mansions here during the Gilded Age.

Visitors can enjoy a variety of outdoor activities on the water, including boating, kayaking, paddle boarding, and lake cruises. There are also a petting zoo, waterpark, golf, hiking, zip-lining, spas, and more.

The highlight is the Lake Geneva Shore Path, a 21-mile walking trail around the lake with stunning views of the forest, water and impressive waterfront homes.

Read about more things to do in Lake Geneva here .

Starved Rock State Park, Oglesby, Illinois

Distance from Chicago: 95 miles

Starved Rock State Park is one of the top attractions in the state of Illinois. The park is an ideal spot to enjoy nature and is filled with stunning sandstone canyons and beautiful waterfalls. This is a great place for hiking with 13 miles (21 kilometers) of trails.

In addition to hiking, visitors can enjoy outdoor activities year round, including horseback riding, ice climbing, cross-country skiing, as well as fishing, kayaking, rafting on the Illinois River.

Matthiessen State Park, Oglesby, Illinois

Distance from Chicago: 96 miles

Indiana Dunes, Indiana

Distance from Chicago: 50 miles

The Indiana Dunes National Park borders the State Park of the same name. The national park offers 15 miles of shoreline along Lake Michigan’s southern shore with wide sandy beaches and towering dunes. Hikers will enjoy 50 miles of trails over rugged dunes, mysterious wetlands, sunny prairies, meandering rivers and peaceful forests.

The three highest sand dunes are all in the Indiana Dunes State Park.

In addition to beaches and hiking, Indian Dunes offers many outdoor year round activities including bird watching, fishing, cycling, horseback riding, kayaking and paddling, snowshoeing, and cross country skiing.

Milwaukee, Wisconsin

Distance from Chicago: 93 miles

Stay: Brewhouse Inn and Suites (boutique hotel housed in what was once the main Pabst brewery building)

Milwaukee is famous for its beer -it is nationally recognized with the nickname “Brew City” due to its nearly two centuries of brewing heritage from multiple past major brewers including Miller Brewing Company, Pabst Brewing Company, and Joseph Schlitz Brewing Company. One of the best things to do in Milwaukee is to tour one of its many breweries. Another interesting attraction is the Harley-Davidson Museum.

Rockford, Illinois

Distance from Chicago: 85 miles northwest from Chicago

The most popular attraction in Rockford is Anderson Japanese Gardens , a 12-acre Japanese garden. Other attractions include the Discovery Center Museum (a great a family museum), Nicholas Conservatory and Gardens, Burpee Museum of Natural History, Tinker Swiss Cottage Museum and the Rockford Art Museum.

South Bend, Indiana

Stay: Aloft South Bend or Morris Inn at Notre Dame (if you want to stay on-campus)

South Bend is famous for being home to the University of Notre Dame but there are many more reasons to visit. There are many attractions on the beautiful, large campus including the Golden Dome, Notre Dame Stadium, the Basilica of the Sacred Heart and the Grotto of Our Lady of Lourdes, a replica of the famous shrine.

One of the best things to see in South Bend is the Studebaker National Museum , featuring a large collection of Studebaker automobiles drawn from the history of the company, beginning with horse-drawn carriages. They also have the carriage that Abraham Lincoln took to Ford’s Theater the night he was assassinated.

For those with a sweet tooth, visit the South Bend Chocolate Company, which is home to one of the largest collections of chocolate memorabilia in the world, including a 1,300-year-old Mayan chocolate pot among the hundreds of tins, containers and chocolate boxes of all shapes and sizes.  Visitors can take a factory tour for a history lesson of chocolate and its origins, as a guide leads guests through all of the factory processes, including panning, enrobing and more, including a test sample at the end. For an extra special treat, you’ll dip a chocolate spoon, walk through the Chocolate Museum and receive 10% off your purchase that day.

Galena, Illinois

Distance from Chicago: 164 miles

Stay: Country Inn & Suites by Radisson

Galena is a short road trip from Chicago but it a great place for weekend getaway whether on a romantic trip or traveling with kids. Galena is a charming and historic small town. A large portion of the city is listed on the National Register of Historic Places and there are many historical sights to explore including the Ulysses S. Grant Home, the Elihu B. Washburne House, Dowling House and the Old Market House.

Some things to do in Galena including shopping downtown at the many boutiques and antique stores, eating at local restaurants and wine tasting at local vineyards. Theere or explore the lush rivers and hiking trails dotted throughout the area. Galena is close to Apple River Canyon State Park , an Illinois state park, where you can go hiking, fishing and more.

Holland, Michigan

Distance from Chicago: 150 miles

Stay: Courtyard by Marriott Holland Downtown

Located on the shores of Lake Michigan, the city of Holland, Michigan, which was founded by Dutch Calvinists in the late 1840s, proudly flaunts its Dutch origins, and is home to canals and a 250-year-old authentic Dutch windmill.

Holland is especially pretty in the spring when you can see colorful tulips in local gardens, parks, attractions and lining the streets. You can see millions of tulips at Veldheer Tulip Gardens . One of the mont popular times to visit is during the Tulip Time Festival , the largest tulip festival in the United States which is held every year in May.

Historic Route 66 Road Trip in Illinois

Distance from Chicago: 301 miles

Historic Route 66 is a classic American road trip . Don’t have time to drive Route 66 all the way from Chicago to California? You can still drive the Illinois portion of historic Route 66 from Chicago to St. Louis. If you prefer a shorter drive, you can also drive from Chicago to Pontiac or Springfield. You will drive past unique roadside attractions, classic diners, kitschy attractions and Route 66 nostalgia.

Some must see stops in Illinois along the way include:

• Joliet (home to the Joliet Museum and Rialto Square Theatre)
• Gemini Giant (a landmark statue at the eastern entrance to Wilmington)
• Pontiac (the Illinois Route 66 Hall of Fame and Museum and the Route 66 Museums are must see attractions)
• Springfield
• Old Chain of Rocks Bridge.

If you are planning to do a long Route 66 road trip, I recommend this EZ66 GUIDE For Travelers , which is considered the best Route 66 guide.

Shawnee National Forest

Distance from Chicago: 300 miles

Stay: Riverview Mansion Hotel (a unique boutique style mansion)

Nestled between the Mississippi and Ohio Rivers in southern Illinois, the Shawnee National Forest is full of natural beauty, making it ideal for outdoor recreation from hiking to climbing.

The stunning Shawnee National Forest landscape features woodlands, hills, lakes, creeks, rock formations, cliffs and bluffs. You can also see wildlife such as bad eagles.

Shawnee National Forest is the best place to go hiking in Illinois with spectacular views. Trails include the long River to River Trail and the Rim Rock National Recreational Trail. The must see attraction is the Garden of the Gods wilderness area featuring ancient sandstone cliffs and formations.  Climbers should not miss the Jackson Falls climb on 60 feet of sandstone cliffs and boulders that include numerous freestanding towers.

If you enjoy wine, The Shawnee Hills Wine Trail features 11 wineries located along a 35-mile scenic drive along highway 127 and highway 51 in the Shawnee National Forest.

Door County, Wisconsin

Distance from Chicago: 244 miles to Sturgeon Bay

Door County , located in the northeast corner of Wisconsin, is a hidden gem full of charming villages and towns, lighthouses, state parks, vineyards, and outdoor attractions and activities.

Sturgeon Bay is a good first stop from Chicago and a convenient base for exploring the area. The city is a fisherman’s mecca, with some of the best bass fishing in the world. You can also tour a restored tug, visit the Door County Maritime Museum, learn the history of Door County, stroll down historic 3rd Avenue, or enjoy nature at Potawatomi State Park on the city’s edge.

Explore one or more of several little towns located along the east and northeast coastline of Door County (including Egg Harbor, Fish Creek, Bailey’s Harbor and Sister Bay) which full of unique shops, galleries, restaurants and breweries.

Bring your car on the 30 minute ferry to Washington island, located northeast of the tip of the Door Peninsula.

You can find a full driving tour of Door County here .

What are your favorite road trips from Chicago ?

Planning a trip to Chicago? Check out my Chicago guides and itineraries:

• 3 Days in Chicago Itinerary + Travel Tips From a Local
• The Perfect Itinerary for One Day in Chicago (According to a Local)
• Most Instagrammable Places in Chicago

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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.

9 Fabulously Unique Places to Stay in Illinois

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10 Road Trips From Chicago That Will Have You Ready To Hit The Gas

Embark on an adventure with these top road trips from Chicago that will inspire travelers to pack up the car and hit the road right away.

Chicago is a modern city with a rich history and culture. It is a gateway to some of the most stunning destinations in the Midwest and among the top ten best US cities for a day trip . Whether travelers are seeking breathtaking scenery, a thrilling adventure, or a break from the routine, a road trip from Chicago is the perfect remedy. This article explores amazing road trips from Chicago that will have people ready to hit the gas and be on the move. These destinations will surely make unforgettable memories and inspire one's next adventure.

1 The Great Lakes Seaway Trail

The Great Lakes Seaway Trail is a scenic byway that stretches over 500 miles along the shores of Lake Ontario, Lake Erie, and the St. Lawrence River. It meanders through forests, passes over small boat channels and tunnels, and crosses thick native oak woodlands. It also passes through historical sites, charming towns, and stunning natural areas like Niagra Falls. It provides an opportunity to experience the serene beauty of the spectacular Great Lakes region that verges on the wilderness.

2 Lake Michigan Circle Tour

The Lake Michigan Circle Tour is one of the most famous road trips in the US . It is a must-see if one is fond of scenic tours. This loop takes people through four states, including Wisconsin, Michigan, Indiana, and Illinois. Some of its great features include beautiful landscapes. The breathtaking beaches of Lake Michigan, historic sites, and lighthouses are also part of this tour.

Route 66 starts in Chicago and ends in Santa Monica, California. This iconic route offers one of the best road trips in the USA . The course takes travelers past diverse landscapes and attractions such as the Ozark Mountains in southwestern Missouri, Meteor Crater in western Arizona, and The Grand Canyon National Park. Take a stop in small towns like Illinois and Gallup, and experience the Midwest hospitality and unique charm.

Related: 13 Interesting Things to Do in Illinois (That Aren't in Chicago)

4 The Lincoln Highway Scenic Byway

Now known as the U.S. Highway 30, the Lincoln Highway Scenic Byway is a historic road trip. From Chicago, the route takes people through Joliet, Aurora, and DeKalb before winding through the countryside and passing through quaint towns like Dixon and Rochelle. Take a stop and explore some historic landmarks, such as the restored gas station in Rochelle and Lincoln Highway Association National Headquarters in Franklin Grove. The Lincoln Highway Scenic Byway is one of the unique weekend trips in the Midwest worth taking if one is looking forward to exploring the natural beauty of this stunning region of the United States.

5 Door County, Wisconsin

Door County is the perfect road trip destination from Chicago for a quiet getaway. It is located on a narrow peninsula between Lake Michigan and Green Bay. Door County is known for its fresh seafood, natural beauty, and stunning villages. Take a scenic drive along the winding roads and stop at the charming towns of Fish Creek and Sister Bay. Visitors can also hike the trails at Peninsula State Park or take a scenic boat tour of the islands.

6 Indiana Dunes National Park

The Indiana Dunes National Park is an appropriate choice for a one-day road trip, just an hour's drive from Chicago. The park features 15 miles of towering dunes, sandy beaches, and lush forests. Visitors can join other hikers, birdwatchers, or beachgoers. Be sure to visit the historic Bailly Homestead and Chellberg Farm, which showcases the lives of early settlers in the region.

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7 Mackinac Island, Michigan

Drive to Mackinac Island for a taste of old-world charm, located in Lake Huron between the Upper and Lower Peninsulas of Michigan. The island is famous for its horse-drawn carriages, Victorian architecture, and lack of motorized vehicles. Board a ferry to the island and explore the historic Fort Mackinac.

8 Starved Rock State Park

Starved Rock State Park is just over an hour's drive from Chicago, making for a perfect short road trip and day out. It is a stunning natural destination for a day trip, with many incredible natural destination signs. Take the park's hiking trails and explore cascading waterfalls, towering sandstone cliffs, and breathtaking canyons. The park offers a stunning natural setting perfect for exploring, camping, and hiking. Use hiking trails to get to the top of Starved Rock and enjoy the breathtaking views of the Illinois River.

Related: Chicago's Best-Kept Secrets: An Adventure To Uncover 10 Most Unique And Offbeat Attractions

9 Harbor Country, Michigan

Harbor Country is one of the many getaway destinations for road trips from Chicago that make leaving the city worth it . It's an 80-mile drive from Chicago. Harbor Country is a perfect antidote to the city's noise due to its relaxed country vibe and outdoor activities on and off the lake. Some very decent wineries are also found in the area. Lemon Creek and St. Julian Winery are great wineries one should consider visiting on one's road trip for the best experience.

10 Michigan's Upper Peninsula

Driving through Michigan's Upper Peninsula from Chicago via the I-43 N is a unique experience that takes people through some of the most stunning landscapes in the Midwest. From Chicago, it's around a six-hour, 380-mile drive. The Upper Peninsula stretches from the southern part of Canada to Wisconsin in America. Scenic waterfalls, towering forests, and crystal-clear lakes are features along the route.

Where to Road Trip from Chicago: 12 Interesting Destinations

• Date: July 18, 2022
• Time to read: 6 min.

There are a lot of great destinations from Chicago! If you have a day or a week, these interesting cities and attractions are great places to visit  on a road trip this summer. 

When you are planning a vacation on a budget there there three factors to consider:

You have control over all these costs, but gas will cost what gas will cost. You have find something closer to home. 

I have a list of destinations that can be exciting no matter how close or far from home your budget can carry you. 

Day Trips from Chicago

These trips will take about an hour from the city and include some really cool sites to see. 

The Vine Martini and Wine Bar

In Greyslake Illinois The Vine is a very popular bar. The relaxed atmosphere of The Vine makes it a great place to visit from Chicago. 

Right down the street there is a great burger place, Twisted Burger and Emil’s Tavern. A great place to spend the evening with friends. 

Cedar Lake (Indiana) 

Cedar Lake is a great trip for hunting for antiques. The Old Goat’s market is a good first stop and you can enjoy learning about the area at the Cedar Lake Historic Museum. 

There are a number of other antique and resale shops for a day of deal hunting. 

Michigan City

Michigan City is just a short drive from Chicago and you can find Casinos, restaurants, outlet shopping and you will cross state lines! 

If you are not into gambling, the lighthouse museum is a high quality educational trip and the outlet shopping is a great girls trip idea. Michigan city is an exciting day trip from Chicago. 

2-3 Hour Trips from Chicago

A two hour trip is a really good distance for traveling with kids or young babies. Experienced travelers often travel for 2-3 hours max between stops. 

Take a page from their book and stop before you get too tired of driving. 

Menomonee Falls

Menomonee Falls is a beautiful destination. The falls are man made waterfall located in Mill Pond Park. The city was once home to a large sugar mill. 

There are a lot of beautiful walking trails, ponds and river walks to enjoy in Menomonee Falls. There are also sunset beer garden events in warm weather. 

Crane Orchards U-Pick and Corn Maze, Fennville, Michigan 

A great fall destination , the Crane Orchards and Corn Maze in Fennville Michigan is a destination worth the drive. 

Be sure to pack your walking shoes and enjoy picking cherries, peaches, apples and pumpkins in season. You can find their seasonal fruit page to let you know what is available to pick. 

I love marking apple picking on my family’s calendar each fall. It is a beautiful memory and such a fun day. 

Davenport Iowa

Right on the banks of the Mississippi Davenport is a great small city. Davenport is considered one of the Quad Cities. 

This area offers riverfront dining, walking trails, shopping, theater and museums. 

The Adler Theater offers comedian tours, live music and Broadway shows. Follow up your show with a river cruise and dinner. 

This vacation is really shaping up and you drove less than 150 miles! 

Indianapolis, Indiana 

There is a large museum in Indianapolis that contains the best preserved T-rex in existence, your dino lover will never forget this three hour drive out of Chicago. 

The museum associate with the Indianapolis Speedway is engaging even if you have never seen a race. When the track is not in use you can take the bus tour of this iconic track. 

Monument circle in the heart of town hosts a farmer’s market, food trucks, coffee and restaurants. This busy area of town has plenty to see and do. 

3-5 Hour Trips from Chicago

Three to five hours is the longest drive I would recommend that you drive without stopping, but you will feel like you really got away. 

If you are traveling with kids I recommend that you read this post about how to plan stops with kids . 

Bowling Green, OH

Bowling Green is a great place to attend really great events and festivals. The National Tractor Pulling competition is hosted here and the Great Black Swamp Art Festival.

They have a wonderful summer activity calendar that is sure to offer something worth seeing.   

Bloomington, IN

If you would like a slower paced trip, head to Bloominton. The small town feel offers plenty to see and do. 

Art museums, sculpture gardens and science museums offer plenty of things to do for the whole family. 

The Wonder Lab Science Museum is a hands-on science museum for the whole family and it would make a great family event. 

St. Louis, MO

Our family has taken several trips to St. Louis and you can read about our favorite STL destinations in the linked post. There is no limit to what you can do in St. Louis. 

When you visit St. Louis you will want to see the Arch, the gateway to the West. The improved grounds are a lovely place to walk and read more about American history. 

There are also a few foods you will want to try while visiting the city:

Frozen Custard

Toasted Ravioli 

St. Louis Style Pizza

The first time I tried pizza from Imo’s Pizza I was surprised. It is a memorable experience, give it a try. 

6-8 Hour Trips from Chicago

Chicago is a great starting point when you want to explore America. If you can budget to drive six to eight hours you will be able to visit some iconic American cities and attractions. 

Erie has the best city website I have seen. There is so much to do in Erie, water parks, historic tours of Lake Erie and AA baseball. 

Request a guide to Erie on their city website. It will give you the most information about how to spend your time in this vibrant diverse city. 

Nashville, TN

Nashville is an unforgettable trip. There is so much to see and hear in Music City. 

The Nashville Zoo is great day or night. Their night light display is a stunning event and a low stress evening event. 

You may also choose to schedule your trip around their incredible Food and Wine Festival. The city has the best hotels and restaurants for any budget. 

You will want to hear some music and venues abound. Check out the calendars for: 

Storytellers Hideaway

Grand Ole Opry 

Ryman Auditorium 

RCA Studio A 

Mammoth Cave National Park

Mammoth Cave National Park is a beautiful destination for camping, hiking, exploring and soaking in nature. 

National Parks can book up quickly so check out my handy guide to when to book your road trip lodging. 

Large families or large groups will enjoy the flexible lodging options in National Parks. I highly recommend this for a family vacation. 

Niagara Falls

Niagara Falls is a bucket list item for many people and it is just a few hours from Chicago!

This popular international tourist destination should be planned well in advance. Check lodging prices frequently and plan accordingly. 

One tip for creating a low stress vacation plan is to hire a local guide. I highly recommend that you consider planning this trip with a travel agent or local guide company so that you can avoid getting stuck in a crowd and missing the experience you dreamed about. 

Memphis, TN

Memphis is the home of bluegrass, soul music and rock and roll. This is an incredible destination for music lovers. 

This is about as far south as you can drive from Chicago in 8 hours , so if you are looking to warm up Memphis is a great destination. 

Festivals, concert cities and museums are all waiting in memphis. 

They have several immersive art experiences as well as a trolly tour that is sure to delight. 

Planning a Road Trip From Chicago

When you are planning a road trip from Chicago I recommend that you start at WithinHours.com this site will allow you to explore different travel radius options from your city.

This can help you uncover hidden gems that you may never have thought of in your area. 

Follow up with this Road Trip Planning guide with a few printable worksheets that can help you stay organized and on budget.

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9 of the best road trips in the USA

US road trips remain ever-present on travel bucket lists the world over.

A true pillar of American folklore, their routes are steeped in history and paint a picture of the USA through the ages, from the Gold Rush to the Cold War.

In the modern day, these routes remain on the travel lists of Americans and tourists alike, all longing to head out on the open road to discover vibrant cities, desert plains, attractive coastlines and enormous mountain ranges.

In a nation that stretches over 3,000 miles from east to west, there are hundreds of routes to take you across the country, whether you want to follow the coast north from California or take a more remote route in Alaska.

Lesser known odysseys such as Route 101 or the Lincoln Highway quickly capture the imagination, while famed highways such as Route 66 dominate the dreams of would-be road trippers. To help you decide which route suits you, we’ve rounded up a list of the best trips across the country.

Chicago to Santa Monica

The USA’s most famous route has been immortalised via a combination of pop culture and nostalgia, despite no longer officially being classified as highway. Today, it remains the holy grail of US road trips.

Stretching for around 2,500 miles from Chicago to the beachfront of Santa Monica (just next to Los Angeles), it provides a taste of times gone by in the US, from kitsch gas stations to the Wild West-like emptiness of the Arizona and New Mexico desert.

This retro feeling is lost at either end of the ‘Mother Road’, especially when arriving into LA, but the marked contrast means that those travelling the route get to experience a quintessential slice of the States, including beautiful desert landscapes, the vintage Americana of Texas and two of the country’s foremost modern cities.

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The Great River Road

Minnesota to louisiana.

This winding route follows the equally serpentine Mississippi River for a total of over 2,300 miles through 10 states. It starts (or ends) in Louisiana, near the Gulf of Mexico, before coursing through Mississippi, Tennessee and ending up in Minnesota, near the Canadian border.

At its start, the route takes travellers across two of of the US’s most famous cities. It begins in New Orleans , the centre of Cajun and Creole culture, and shortly after passes through the capital of blues, soul and rock’n’roll: Memphis , Tennessee.

The rest of the route is renowned for showcasing an abundance of different natural landscapes that only a country as geographically diverse as the US could provide. The wetlands and bayous of Mississipi and Louisiana, including the Atchafalaya Basin, will be the most alien environment to many visitors, with a distinctly eerie, almost rainforest-like feel.

Following along the Mississippi, drivers will see flat plains, mountains and extensive woodland as the route crosses Arkansas, Kentucky, Iowa and Wisconsin, before finishing in Minnesota, “the Land of 10,000 Lakes”.

Lincoln Highway

New york to san francisco.

Though no longer in existence as a single route, a little research will help you take on a section – or all – of the 3,389-mile long transcontinental route that was originally conceived in the 1910s. The route started in New York City and extended all the way to Lincoln Park in San Francisco , taking in 14 states including Ohio, Illinois, Nebraska, Utah and Nevada. Today, much of the road is now Route 30, from Pennsylvania to Wyoming – avoid the freeways of the I-80 for a trip with less motorway and more character.

Today, driving the route is easier in some states than others due to different standards in maintaining the route’s heritage, but this highway will take you across roughly 700 cities and towns, from small-time American settlements to big-hitters like Chicago and Pittsburgh. Along the way, you can learn about the history of both the highway and early America, visit 19th-century mining towns and see some delightful nature, including parts of Lake Tahoe and the Utah desert.

Los Angeles to Olympia, Washington

Route 101 traces the US’s Pacific Coast from California up into Washington, offering some of the best coastal views in the country. Though it technically starts in Los Angeles , you can begin the route from near the Mexican border, close to San Diego, all the way up to the border with Canada.

The route is split into different sections of road in each state. The first section is California State Route 1, also known as the Pacific Coast Highway, which offers the first uninterrupted sightings of the turquoise waters of the Pacific. It carries on through San Francisco and across the Golden Gate Bridge, passing through the famous wine regions of the Napa Valley and Sonoma County, before picking up the Oregon 101.

Oregon’s coast is home to raw natural beauty, captured in the rugged, unspoilt coastline of areas like Cannon Beach and the valleys of the Columbia River. You continue along the river as you enter Washington, eventually circling the Olympic Peninsula and its mountains before finishing near Olympia’s State Capitol Building.

Richardson Highway

Valdez to fairbanks.

Shorter than many US trips, but certainly no less scenic, the Richardson Highway extends for “just” 364 miles between the cities of Valdez and Fairbank. Alaska offers some of the wildest natural landscapes in America, perhaps best compared to parts of Iceland when viewing its large glaciers, towering peaks, dramatic gorges, steep waterfalls and the Valdez glacier lake.

Various locations offer a host of activities such as white water rafting, hiking, fishing and even ice climbing (as well as views of the Trans-Alaskan Pipeline). Both Valdez and Fairbanks have a range of things to keep you busy too, from lake cruises and whale watching to skiing and Northern Lights spotting.

The Atlantic Coast

New york to florida keys.

Another road trip that gets to roughly 2,000 miles but can easily be split up into manageable sections, a trip down the Atlantic Coast is a worthy alternative to its Pacific counterpart. There is no defined route, with some beginning as far north as Bar Harbor in Maine, and others starting in NYC . If you do start in Maine, you’ll have the option to explore Boston, Rhode Island and the Hamptons, as well as the Big Apple.

Continuing south towards Miami , you can travel through Philadelphia, Washington D.C. and Atlantic City, the East’s answer to Las Vegas. If you stick to the coast rather than heading to the capital, you’ll go through Delaware before crossing a tiny section of the Atlantic over into Virginia Beach.

Carrying on through North and South Carolina, you’ll eventually reach Florida , first via Jacksonville and then Orlando if you fancy a small detour. From Miami you’re on the home stretch, but not before you cross arguably the highlight of the entire trip – the 113-mile Overseas Highway, which extends over the Atlantic between Miami and Key West, the final stop.

Road to Hana

Hana to kahului.

Hawaii may not be the first destination that comes to mind when thinking of road trips, with the Polynesian-influenced State home to a fascinating local culture, laid-back towns and coastline so picturesque it’s scarcely believable. But one small route stands out on Maui that’s as beautiful as those famed beaches – the Hana Highway, which links the towns of Hana and Kahului.

Running for just 64 miles, this coastal route usually takes around three hours to drive due to speed limitations and around 600 bends, winding through dense jungle and passing over imposing cliffs while tantalisingly close to the emerald waters of the Pacific.

Western Highlights

San francisco to las vegas.

This trip takes in some of the US’s most famous landmarks and cities, passing through California , Nevada and Arizona.

Begin in charming San Francisco, where innovation, forward-thinking and counterculture have combined to form a bohemian city backed by national landmarks like the Golden Gate Bridge. The first stop on your route will be Yosemite National Park, a land of surreal landscapes including giant sequoias, the 914-metre vertical rock face of El Capitan and North America’s tallest waterfall, Yosemite Falls.

Continue on a slightly longer drive southeast towards Los Angeles, where you’ll need a few days to take in the sights of Hollywood, Santa Monica, Malibu and the rest, before continuing on to the Grand Canyon via the I-10 or I-40 freeways.

Red rock hills and desert plains will quickly come into sight before you reach what is undeniably one of America’s most famous, and impressive, natural sites. Explore, hike and marvel at the vast sandstone cliffs and winding waterways, before spending the night in a rustic mountain cabin. This grandiose trip finishes in equally extravagant Las Vegas , the US’s undisputed home of hedonism.

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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!*

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23 Incredible Road Trips in the U.S.

Whether you’re looking for sweeping views of the pacific ocean or a multiday adventure through national parks, these road trips provide plenty of opportunities to explore the united states..

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Glacier National Park is one of many scenic places you can visit on an American road trip.

Photo by Zack Frank / Shutterstock

In a country as large as the United States, there’s no shortage of destinations and detours to explore by car . Whether your idea of the perfect American road trip entails an epic, cross-country journey or a shorter jaunt through a few of its most iconic national parks , your options are as large and varied as the country itself.

Even if you don’t have the time to drive cross-country, there are plenty of road trip routes (ranging from three days to a week or longer): classic California itineraries , New England routes that shine especially well in the fall, scenic East Coast adventures, and a variety of Midwest journeys for folks farther from the coasts.

No matter your mode of transportation—be it van, RV, motorcycle, or four-door sedan—these are 21 of the best road trips in the nation to consider.

Plan your next Route 66 trip around thirst-quenching stops.

Photo by Peek Creative Collective/Shutterstock

There are many ways to do a cross-country road trip in the USA, but these two itineraries will take you through some truly iconic American places.

1. Chicago to Los Angeles: A Whiskey Road Trip on Route 66

It doesn’t get more American than a 2,000-mile drive along the entirety of Route 66. There are endless ways to take this legendary trip (including an EV version —but to take your cross-country road trip to the next level, we recommend exploring another American pastime: whiskey.

Starting in Chicago and ending in L.A., you’ll stop by some of the leading craft distilleries in the United States, like Few Spirits in Chicago, Still 630 in St. Louis, and Red Fork Distillery in Tulsa. In between tastings, make time for detours to natural attractions, like the Grand Canyon, and quirky roadside curiosities, like Cadillac Ranch in Amarillo, Texas. Just remember to drink responsibly—this is a road trip after all.

Plan your trip

The full itinerary: Put a New Twist on Route 66—Make It an American Whiskey Road Trip

No cars are allowed on Mackinac Island, so you need to park before taking the ferry to this spot.

Photo from Shutterstock

2. Bangor, Maine, to Seattle, Washington: The Great Northern on U.S. Route 2

Covering both the U.S. and Canada, a cross-country trip along U.S. 2 is ideal for anyone who wants to experience the vast diversity and expansiveness of North America. This drive runs the entire top border of the U.S. and showcases otherworldly natural wonders like Acadia National Park in Maine, the Apostle Islands National Lakeshore in Wisconsin, and Mackinac Island in Michigan. The route also passes through Canada, taking road-trippers through Ontario into Quebec—this route may focus on nature, but you won’t want to miss a stop in Montreal or Ottawa.

You’ll also get to explore Montana and Glacier National Park ( reservations may be required ) before passing the Columbia Plateau and ending in the Pacific Northwest’s largest city, Seattle. Don’t miss spending time in the Olympic Peninsula (home to Olympic National Park) for a peek at one of the most scenic places on the West Coast.

3. Dana Point to San Francisco: Driving California’s Pacific Coast Highway

The seemingly endless views of the Pacific Ocean along Highway 1 (also known as the Pacific Coast Highway) are what road trip dreams are made of, and exactly what makes this California road trip so popular. However, with so many stops along the 655-mile stretch, we pulled together a list of the ones well worth pulling over to view. Don’t miss the perfect surfing waves in Santa Cruz, seasonal cuisine in Malibu, an afternoon a the boardwalk in Santa Monica, or a night in Big Sur as you drive between Dana Point (just south of Los Angeles) and San Francisco.

• The full itinerary: The Best Stops for a Road Trip on the Pacific Coast Highway
• The AFAR Guide to San Francisco

The seaside town of Monterey was the setting for John Steinbeck’s Cannery Row .

Photo by Denise Lett/Shutterstock

4. Big Sur to Mono County: A Literary Road Trip Through Northern California

Yes, this itinerary requires you actually put down your book to drive, but seeing some of the pivotal places that shaped American authors will be so worth it. Follow in the footsteps of writers like Jack Kerouac, Maya Angelou, and Amy Tan on this road trip that takes you through literary landmarks in Northern California, such as Caffe Trieste, a meeting place for Jack Kerouac, Allen Ginsberg, Alan Watts, and other bohemian writers and thinkers. This 12-stop itinerary is perfect if you live in the San Francisco Bay Area because you’ll be able to stay make these trips in one or two days.

The full itinerary: The California Road Trip All Book Lovers Should Take

Arizona may take its nickname from the Grand Canyon, but the state has far more natural wonders than just that one.

Courtesy of Shutterstock

5. Phoenix to the Grand Canyon: An Iconic Arizona Road Trip

This 240-mile Arizona road trip takes travelers along some of the state’s most iconic highlights, including its most famous one, the Grand Canyon. A great itinerary for first-time visitors and returning travelers alike, it offers plenty of opportunities for scenic drives, hiking, and biking—as well as tasty food along the way. Hike the 2,704-foot-tall Camelback Mountain in Scottsdale or take in the beautiful red rocks of Sedona on a hike to Cathedral Rock while exploring the Grand Canyon State.

• The full itinerary: The Classic 5-Day Arizona Road Trip
• Grand Canyon guide: The First-Timer’s Guide to the Grand Canyon
• Where to eat in Phoenix: A Chef’s Guide to the Best Restaurants
• Where to stay: The Best Hotels in Arizona ; The Best Airbnbs in Sedona

The Delicate Arch living up to its name in Utah’s Arches National Park

Photo by tusharkoley / Shutterstock

6. Zion to Grand Canyon: A National Parks Road Trip in the Southwest

If you’re looking to visit as many national parks as possible in one road trip, this southwestern itinerary is for you. This journey through Utah and Arizona lets you hike Angel’s Landing in Zion, feel tiny under Delicate Arch in Arches National Park, explore Fairyland Loop Trail in Bryce Canyon, and, of course, raft down the Colorado River in the Grand Canyon. Most visitors to the Grand Canyon remain on the rim, but take at least four days to venture within the canyon and take advantage of the trails and river rafting.

• The full itinerary: The Ideal Road Trip Through U.S. National Parks
• Utah’s 8 Best National Parks and Monuments
• 10 Best National Parks and Monuments in Arizona
• The First-Timer’s Guide to the Grand Canyon

Stop and admire the winding roads of the San Juan Skyway.

Photo by Anh Luu/Shutterstock

7. San Juan Scenic Skyway Road Trip: An Adventure Through Southwestern Colorado

This Colorado trip takes you along the 232-mile loop of the San Juan Scenic Skyway, where you will see plenty of alpine forests, mining towns, and craggy peaks. And for anyone looking to enjoy refreshments after a long day of driving, this route features many opportunities to stop at some of the best breweries in Colorado , such as Ska Brewing Co. in Durango.

• The full itinerary: The Ultimate Southwestern Colorado Road Trip
• Five Classic Colorado Road Trips To Take This Year

In small-town Buena Vista, the riverfront Surf Hotel offers front-row seats to Colorado-style adventure seekers.

Courtesy of the Surf Hotel

8. Denver to Montrose: A 420-Mile Road Trip Through Colorado

Want to explore even more of the Centennial State? Head out on this weeklong road trip where you can fish for salmon in Colorado’s largest reservoir, visit numerous small towns, like Paonia and Crawford, with thriving art scenes along the Colorado Creative Corridor , and explore Black Canyon of the Gunnison National Park, one of the least visited national parks in the nation.

• The full itinerary: Art Stars, High-Altitude Wines, and a Remote National Park: The Ultimate Colorado Road Trip
• Where to stay: The Best Hotels in Colorado
• The AFAR Guide to Denver

Portland may be Oregon’s largest city, but with a population of some 652,000 (or 2.5 million in the larger metropolitan area), it isn’t intimidatingly large.

Photo courtesy of Travel Portland

9. Portland to Astoria: An Oregon Coast Road Trip for Outdoor Lovers

If you love the outdoors, then this six-day road trip along the coast of Oregon is for you. After driving to Coos Bay from Portland, travelers will meander along Oregon’s dramatic, rocky coastline, discovering some quintessentially Pacific Northwest vistas along the way: evergreen forests, seaside dunes, and marine ecosystems. Between stops, there are ample opportunities to stretch your legs hiking, kayaking, or strolling around the region’s small towns—like the historic old town in Florence.

Of course, it wouldn’t be an Oregon road trip without a stop (or three) at a craft brewery, such as Fort George Brewery in Astoria, or cozy coffee shop, like Bread & Roses in Yachats.

• The full itinerary: An Outdoor Lover’s Road Trip on the Oregon Coast
• The AFAR Guide to Portland

The State Capitol Building in Nashville marks the end of this road (trip).

Photo by photo.ua / Shutterstock

10. Seneca Falls, New York, to Nashville, Tennessee: Follow the Path of the Women’s Suffrage Movement

Starting in New York’s Finger Lakes region and ending at the State Capitol Building in Nashville, this road trip traces the route of the national women’s suffrage movement. Highlights include stops at the Susan B. Anthony Museum & House ; Union Square in New York City, which was the site of the first suffrage march; and the Belmont-Paul Women’s Equality National Monument in Washington, D.C.

• The full itinerary: Celebrate Women’s Suffrage on an Epic, Self-Guided Road Trip
• Where to stay: The Best Hotels in Nashville
• The AFAR Guide to Nashville
• The AFAR Guide to Washington, D.C.

Asheville is one must-stop on a North Carolina road trip.

Courtesy of ExploreAsheville.com

11. Charlottesville to Asheville: A Scenic Road Trip Through Virginia and North Carolina

The Blue Ridge Parkway is one of the most scenic drives in the country. Beginning in the soft hilly meadows of the Appalachian Mountains from Shenandoah National Park down into the Blue Ridge Mountains, then into the Great Smoky Mountains, this five-day road trip is best done at a slower pace, which is perfect for admiring the dramatic outlooks and green plateaus. This eclectic itinerary features stops at an art museum, a dairy farm, and plenty of hiking trails.

• The full itinerary: The Ultimate Blue Ridge Parkway Road Trip
• Where to stay: 12 Dreamy Blue Ridge Mountain Cabins You Can Rent on Airbnb and Vrbo
• 8 U.S. National Park Road Trips to Take in Your Lifetime

Dowa:kwe dance group from Zuni Pueblo in 2019

Courtesy of Indian Pueblo Cultural Center

12. Albuquerque to Las Cruces: Discover New Mexico on This Three-Day Road Trip

This route steers you away from New Mexican tourist hot spots like Taos and Santa Fe and instead takes you on a three-day adventure with places that teach you about Pueblo history. You’ll stop at Indian Pueblo Kitchen (formerly known as Pueblo Harvest), a restaurant inside the Indian Pueblo Cultural Center that features Indigenous cuisine ; pick up peppers at Three Brothers in Hatch; and slide down the dunes in White Sands National Park.

• The full itinerary: This New Mexico Road Trip Is the Perfect Introduction to the Land of Enchantment

Historic Fort Martin Scott is one of the places travelers can visit to learn about Fredericksburg’s history.

Photo by Mark König/Unsplash

13. A Five-Day Scenic Road Trip Through Texas Hill Country

This Texas road trip starts and ends in San Antonio with stops in small towns like Bandera, Boerne, and consider a stop in Fredericksburg, which is one of AFAR’s best places to go in 2024 ). Over five days, you’ll find opportunities to stroll in a Japanese tea garden in San Antonio, relax along the Sabinal and Frio Rivers by inner tube, and eat as many tacos as you want. Seriously: You could eat tacos for every meal on this road trip and not get tired of them.

• The full itinerary: Tree Houses, Tubing, and Tacos: The Ultimate Texas Hill Country Road Trip

Mount McKinley looms large on a drive through Denali National Park.

Photo by warnsweet / Shutterstock

14. A Weeklong Road Trip Through Alaska’s Most Majestic Sights

This weeklong drive in Alaska starts and ends in Anchorage. You travel along four scenic byways; explore Wrangell–St. Elias wilderness, the largest U.S. national park; catch sight of Denali, the tallest peak in North America; and enjoy the surprisingly stellar food scene of McCarthy, a one-road town with only a couple dozen residents.

• The full itinerary: Glaciers, Mountain Peaks, and Organic Farms: The Ultimate Alaska Road Trip
• Which Alaska National Parks Should You Visit?

More than geothermal pools, Kirkham Hot Springs features a piping-hot waterfall.

Courtesy of Idaho Tourism

15. Boise to Sun Valley: Explore Idaho’s Scenic Byways

Even a short road trip can be packed with adventure, good food, and scenery, which is exactly what this trip from Boise to Sun Valley along Idaho’s Ponderosa Pine Scenic Byway offers. Although the drive only takes six hours, we recommend taking a few days to explore all the stops and detours along the way. One can’t-miss spot is the Kirkham Hot Springs , where you can stand under a waterfall that will splash you with 135-degree mineral water year-round.

• The full itinerary: The Little-Known Idaho Road Trip You Need to Drive
• Things to do: The Best Outdoorsy Things to Do in Idaho

Grand Portage State Park is the only state park jointly managed by a state and a Native American band.

Photo by Shutterstock/QZ

16. Duluth to Grand Portage State Park: A Scenic Minnesota Sampler

Although there are many appealing road trips throughout the Midwest, this 143-mile, three-hour circuit, which starts and ends in Duluth, Minnesota, is worth keeping in mind. Meandering north on MN-61 with this itinerary, you will enjoy prime views of Lake Superior and towns like Grand Marais, as well as Grand Portage State Park, home to waterfalls, hiking trails, and opportunities to learn about the Ojibwe community who occupy the land today. Once back in Duluth, enjoy a beer at Canal Park Brewing Company before checking into the waterfront Canal Park Lodge nearby.

• The AFAR Guide to Minnesota

Wind your way through colorful foliage in New Hampshire.

Photo by Shutterstock

17. Kancamagus Highway: A Quintessential New England Drive

Yes, you can take a road trip in New England at any time of the year , but this region shows off its best colors in the fall, when locals and tourists alike head out into the country to view the changing colors of the trees. Join other admirers of fall foliage on this popular, 34.5-mile road trip along New Hampshire’s Kancamagus Highway, colloquially known as the “Kanc,” for picturesque ponds, hiking trails, and scenic overlooks.

• Plan Your Fall Getaway With This Peak Foliage Prediction Map

Ogunquit is home to the small, postcard-perfect harbor of Perkins Cove.

Photo courtesy of QualityHD / Shutterstock

18. Maine’s “Lobster Trail”: Travel Route 1 Along the Coast

Traveling Route 1, affectionately known as “the lobster trail,” along Maine’s jagged coastline is an exercise in indulgence. Sample lobster dishes in all forms—buttered, steamed, on a roll, or even in a decadent mac-and-cheese.

The trip starts in the quaint small town of Ogunquit , with its rare (for the area) 3.5 miles of white-sand beach. Make your first lobster of the journey count, steamed with a side of drawn butter at Barnacle Billy’s in picturesque Perkins Cove harbor. Stop at Big Daddy’s for a cone on your way to the shipbuilding center—and summer home of George H. W. Bush—Kennebunkport. Stay at the recently redesigned 150-year-old classic White Barn Inn , and consider a sailing trip for an afternoon. With lobsters cooked in ocean water, the legendary lobster roll at the Clam Shack is a must.

• 8 Scenic East Coast Road Trips to Take This Year

Throughout North Carolina’s Piedmont region, innovative restaurants, shops, and restaurants like Leah & Louise in Charlotte, above, are creating a buzz.

Photo by Peter Taylor Photography

19. Raleigh to Charlotte: A 4-Day Trip Through North Carolina’s Reinvented Core

North Carolina’s Piedmont region extends from the coastal plain to the Blue Ridge Mountains, and includes farmland and rolling wooded hills, especially on the 1-40 stretch near Hillsborough. Starting in Raleigh, drive the short distances to Greensboro, Winston-Salem, and Charlotte to see how these cities are innovating through art, food, and a celebration of the past. Take your time—four days should do—to experience downtown arts districts, James Beard Award–winning restaurants, and civil rights museums that speak truths. Plan your trip

• A Road Trip Through North Carolina’s Reinvented Core

Scenic South Walton is part of the Emerald Coast of Florida.

20. Scenic Highway 30A: A Sunday Drive Through South Walton, Florida

Florida is full of places to cruise with the top down, but it’s hard to beat a Sunday (or any day) drive along Scenic Highway 30A through northwest Florida, home to a postcard-perfect stretch of seaside towns known as South Walton.

The roughly 28-mile route through South Walton County kisses the coast for nearly all its length, taking you through gorgeous residential Gulf-front communities like Rosemary Beach, Grayton Beach, and Blue Mountain Beach . Roll down the windows and let the emerald-hued views in.

Pull over to explore, too—maybe to admire the New Urbanism architecture in Alys Beach or to swim in the clear waters at Grayton Beach State Park . (The beach here has been lauded among the best in the world.)

• The full itinerary: The Florida Road Trip You’ve Been Missing

Stand-up paddleboarding is just one way to enjoy a Florida Keys sunset.

Shutterstock

21. The Florida Keys: An Island-Hopping Getaway

For a sunny road trip itinerary in Florida, skip Miami and head farther south. Beginning in Key Largo and ending in Key West, the Florida Keys Scenic Highway is often overlooked for more well-known routes up north, but it is well worth going out of your way to experience.

As the name suggests, this route is very scenic, so plan to spend at least a few days exploring it and numerous stops along the way. Some highlights include driving across the impressive Overseas Highway, stopping to admire art in the town of Islamorada, and enjoying the historic sites, food, and (of course) beaches in the city of Key West.

• The full itinerary: How to Road Trip in the Lesser-Known Florida Keys

Sun Studio in Memphis was the site of the famous Million Dollar recording session that brought together Elvis Presley, Jerry Lee Lewis, Carl Perkins, and Johnny Cash.

Photo by f11photo on Shutterstock

22. Memphis to Bristol, Tennessee: A Music-Driven Adventure

If you have about a week to spare and a deep appreciation for music, take a road trip from one side of Tennessee to the other, starting in Memphis and ending in Bristol. The eastbound trip spans genres, including rock ( Graceland ), blues ( Beale Street) and, of course, country (did you really go to Tennessee if you didn’t go to Dollywood ?). Nashville serves as the halfway point on your journey—so consider penciling in an extra 48 hours to fully explore the state capital’s greatest hits.

• The full itinerary: 5 Great American Road Trips For Music Fans

The stunning coastline near Cueva del Indio has been the backdrop of star-studded films.

Photo by Alexsf.gr/Shutterstock

23. Arecibo to Condado, Puerto Rico: A Lesser-Known Side of a Well-Loved Island

In the minds of many, trips to Puerto Rico bring images of stunning beaches , delicious foods , and maybe a bioluminescent bay or two . But there’s plenty of history to be found here, too, as Puerto Rico was home to an Indigenous population known as the Taino, a heritage many Puerto Ricans embrace. That history can be explored via a road trip. Starting in the northern town of Arecibo, travel south to Ponce, then back north to Condado—along the way you’ll encounter petroglyphs, Indigenous sites, and breathtaking natural spots.

• The full itinerary: A Puerto Rico Road Trip That Puts Indigenous Culture First

Additional road trip planning resources Picking the route for your road trip is only one part of your planning. From what snacks to pack to which podcasts to listen to, these additional resources will help you prepare for your next adventure:

• Best road trip snacks
• Road trip planning apps
• Podcasts and audiobooks to download
• What to pack for a road trip

This article originally appeared online in August 2020. It was most recently updated on April 4, 2024, to include current information. Additional reporting by Jessie Beck, Erika Owen, Ray Rogers, Terry Ward, and Sheryl Nance-Nash.

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.

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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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USA TODAY 10Best

10 best marathons in the United States for 2024

Best Marathon (2024) April 3, 2024

The United States hosts around 1,000 marathons every year, the largest of which see tens of thousands of endurance runners crossing the finish line and conquering the grueling 26.2-mile distance.

To find the top races, USA TODAY 10Best editors and a panel of experts made their nominations, then readers voted for their favorites. Here are the 10 best marathons across the nation for 2024.

No. 10: Hatfield McCoy Marathon - Williamson, West Virginia

The longest-running marathon in the states of Kentucky and West Virginia is the popular Hatfield McCoy Marathon, which traverses both states on its journey. Named after the infamous Hatfield-McCoy feud, the challenging course takes runners through the rugged and beautiful Appalachian Mountains and includes both road and trail sections. 

No. 9: Honolulu Marathon - Honolulu, Hawaii

After New York, Chicago, and Boston, this is the fourth largest marathon in the United States. It's tropically scenic and warm, and there's no time limit, so everyone is allowed to finish, making it a great first-time marathon race. The course runs through downtown Honolulu and its famed Christmas lights, through Waikiki and up around Diamond Head, to a stunning oceanside finish in Kapiolani Park. The post-race treats are also legendary, with everyone getting fresh Hawaiian malasadas (scrumptious local versions of donuts dusted with sugar).

No. 8: Bank of America Chicago Marathon - Chicago, Illinois

One of the six World Marathon Majors, the Bank of America Chicago Marathon is typically held on the second Sunday in October. The flat, fast course takes runners past iconic Chicago landmarks on its journey through 29 neighborhoods, starting and finishing in Grant Park. This popular race attracts more than a million spectators each year.

No. 7: Shiprock Marathon - Shiprock, New Mexico

Held the first weekend of May, the Shiprock Marathon takes runners through the rugged desert landscapes of the Navajo Nation. Along the way, participants enjoy a variety of live music to motivate runners, adding to this unique and memorable running experience. 

No. 6: CNO Financial Indianapolis Monumental Marathon - Indianapolis, Indiana

CNO Financial Indianapolis Monumental Marathon is a good qualifying event, as the USATF-certified course is flat and fast. You'll run through the heart of Indianapolis' historic neighborhoods and enjoy Hoosier hospitality before finishing near the Indiana State House. With a November date, you'll get crisp fall weather, and the final stretch is all downhill, so this is a great marathon for first-time long-distance aspirants. 

No. 5: Coast Guard Marathon - Elizabeth City, North Carolina

If you've ever wanted a running tour of a military base, this one's for you. The Coast Guard Marathon runs through the U.S. Coast Guard Base Elizabeth City, along the Pasquotank riverfront, and even takes participants on the runway and around one of the last standing WWII airship hangars. Registration is open to both military personnel and civilians. 

No. 4: Big Sur International Marathon - Big Sur, California

Famed for its stunning views of the Pacific Ocean, rugged coastline, and picturesque scenery, the Big Sur International Marathon is a favorite among runners and nature lovers alike. In addition to breathtaking vistas, this challenging course features significant elevation changes on its route from Big Sur, north along Highway 1, to the finish line in Carmel. The USATF-certified course has been called “one of the jewels of American running.”

No. 3: Marine Corps Marathon - Arlington, Virginia

Known as "The People's Marathon," the Marine Corps Marathon honors the dedication and sacrifice of the United States Armed Forces. The race is known for its rich history and is one of the largest marathons in the world. With a course that winds through the streets of Arlington, Virginia, and Washington, D.C., the route passes many of the area's famous landmarks and monuments, including the National Mall and the U.S. Capitol.

No. 2: New York City Marathon - New York City, New York

Known for its enthusiastic crowd support, the famous New York City Marathon embodies the spirit and energy of the city where it takes place. A celebration of diversity and inclusivity, runners from all over the world come together to participate in this iconic event. The course takes runners through all five boroughs of the city, starting in Staten Island and finishing in Central Park. Along the way, runners pass by many of the city's famous landmarks, including the Verrazzano-Narrows Bridge, the Empire State Building, and Times Square.

No. 1: Cincinnati Flying Pig Marathon - Cincinnati, Ohio

The Flying Pig Marathon is loved by runners, and for good reason. It's fun, with pig motifs used everywhere, from the "pig pen" corrals where different speed groups are segregated, to crossing the "finish swine" and attending the post-race party with pizza and beer. The course is also super attractive, albeit hilly, running through the most diverse and scenic neighborhoods of Cincinnati and surrounding townships, and alongside the Ohio River. Finishers get medals and mylar blankets to go with all the post-pig party refreshments. 

About 10Best Readers' Choice Awards

Nominees are submitted by a panel of experts. 10Best editors narrow the field to select the final set of nominees for the Readers’ Choice Awards. Readers can vote once per category, per day. For any questions or comments, please read the FAQ or email USA TODAY 10Best .

The Experts

Amy bushatz.

Amy Bushatz is the host and producer of the  Humans...   Read More

Amy Bushatz is the host and producer of the  Humans Outside podcast. A news reporter and editor based in Palmer, Alaska, Amy spends her time ultra running and recreating in the Alaskan wilderness, volunteering in her small town and experiencing everything Alaska has to offer. Her work on outdoors, travel and fitness has appeared in the Washington Post, Runner's World and Market Watch.  Find her at Humans Outside on Instagram. 

Brittany Vermeer

Brittany (Bevis) Vermeer  is a writer,...   Read More

Brittany (Bevis) Vermeer  is a writer, photographer, and media specialist with 15+ years of experience in the world of sports journalism. She and her husband are triathletes who live in Florida, and she chronicles their multisport adventures on her blog, Triple Threat Life.  

Dave Thompson

Dave is an international travel writer and founder...   Read More

Dave is an international travel writer and founder of Dave’s Travel Corner, a premier travel resource since 1996. He is well-traveled (180 countries & territories); while on the road he enjoys the outdoors, backpacking, mountain climbing, meeting people, and experiencing other cultures.   In 2006, he conceived the  Napa Wine Project , a challenging endeavor to visit, taste with and extensively write about every winery in Napa Valley, California. He has now completed 1,100+ visits and written reviews of Napa wineries & producers.

Hilary Topper

Hilary JM Topper, MPA, is a renowned author and...   Read More

Hilary JM Topper, MPA, is a renowned author and entrepreneur. She has penned two successful books on social media marketing, “Everything You Ever Wanted to Know About Social Media,” published in 2008, and "Branding in a Digital World,” first published in 2019 and updated in 2023. She also wrote a compelling memoir/self-help book, "From Couch Potato to Endurance Athlete," published by Meyer & Meyer Sports in 2022. In addition to her literary achievements, Hilary serves as the CEO of HJMT Public Relations Inc., and the president of HJMT Media Company LLC. Under her leadership, these companies produce two engaging blogs – NY Lifestyle Blog (HilaryTopper.com) and  ATriathletesDiary.com . Beyond her blogging endeavors, Hilary hosts two podcasts, "Hilary Topper on Air" and "Hilary Topper on Air: The Endurance Sports Edition." Her expertise in digital communications extends to education, where she imparts her knowledge as an adjunct professor at Hofstra University. As an influencer on social media, Hilary works with brands to promote their products on platforms like Instagram. Currently, she is working on her fourth book. 

Kayla Jeter

Kayla Jeter  is a Chicago-based athlete and...   Read More

Kayla Jeter  is a Chicago-based athlete and lululemon ambassador, community consultant, and wellness coach helping professional clients and community members design sustainable healthier lifestyles as a trained behavior change coach and certified functional strength coach. Her expertise has been featured on SHAPE, well + good, ESSENCE, and SELF. For almost a decade, Kayla has leveraged digital content as a coaching tool, community connector, and empowerment of shared human experiences on Instagram , TikTok (@fitandfullbykayla), and Pinterest reaching over 110,000 followers worldwide. Kayla is on a mission to disrupt + diversify homogenous spaces in sports and the wellness industry and in doing so, expand possibilities for BIPOC runners to see themselves not only surviving but thriving in these spaces. Through her annual virtual 100MilesofSummer challenge, she empowers over 260,000 humans of all ages and fitness levels around the world to commit to better health through movement by logging 100 miles walking, jogging, running or rolling starting May 1st to August 31st for the last six years. Kayla is a Cleveland, Ohio native who was exposed to different communities and cultures while playing volleyball at the University of Tennessee, professionally in Finland, and coaching at the University of Cincinnati. After the loss of her father to a sudden heart attack in 2016 and the slow decline of her mother to cancer in 2019, Kayla made it her mission to help others understand the necessity of everyday self-care and stress management. Kayla is a 3x World Marathon Major finisher (all in 2023) and will be running her first ultramarathon in March 2024 with lululemon; FURTHER. the lululemon FURTHER feat is a 6-day race focused on supporting + elevating women in ultramarathon running.

Kelly Roberts

Head coach and creator of the Badass Lady...   Read More

Head coach and creator of the Badass Lady Gang, Kelly Roberts’ pre-BALG fitness routine consisted mostly of struggling through the elliptical and trying to shrink her body. It wasn’t until hitting post-college life, poised with a theatre degree, student loans, and the onset of panic, that she found running. Running forced Kelly to ditch perfectionism and stomp out fear of failure. Viral selfies from the NYC half marathon struck a chord with women who could relate to the struggle, and soon the global women’s running community Badass Lady Gang was born. BALG is about enjoying life with a side of running. Kelly’s philosophy measures success by confidence gained, not pounds lost. If you aren’t having fun, it’s time to pivot. Kelly is an RRCA certified coach and has completed Dr. Stacy Sims ‘Women Are Not Small Men’ certification course helping coaches better serve their female athletes. Over the years Kelly has coached thousands of women from brand new runners to those chasing Boston marathon qualifying times, appeared on the cover of Women’s Running Magazine, and created a worldwide body image empowerment movement called the Sports Bra Squad. She lives in Brooklyn, New York.

Laura Norris

Laura Norris is the owner and coach...   Read More

Laura Norris is the owner and coach behind Laura Norris Running. She has a Master of Science in Applied Exercise Science, is a certified personal trainer through the National Strength and Conditioning Association, a certified sports nutritionist through the International Society of Sport Nutrition, and a certified running coach through RRCA and VDOT. She practices evidence-based coaching blended with a holistic treatment of the athlete as an individual. In her 7+ years of coaching, she's coached over 400 runners, from first-time racers to podium finishers. Her personal bests include a 1:34 half marathon and 3:29 marathon. She lives in Colorado with her husband, daughter, and two dogs. 

Lily Fang is a marathoner and blogger at  Imperfect...   Read More

Lily Fang is a marathoner and blogger at  Imperfect Idealist, where she writes race reviews, GPS watch comparisons, and conscious lifestyle content. She's done 7 marathons and 9 half marathons across the US and Europe, as well as a 50k and a few triathlons. You can follow her running and travel adventures on  Strava  and  Instagram .

Marnie Kunz

Marnie Kunz is a Brooklyn-based fitness trainer,...   Read More

Marnie Kunz is a Brooklyn-based fitness trainer, running coach, and blogger and the founder of  Runstreet.com . She loves to participate in fun and unique running events around NYC. You can follow her running adventures on the  Runstreet blog  and  @Runstreet on Instagram . 

Zach Nehr is a freelance writer, professional...   Read More

Zach Nehr is a freelance writer, professional cyclist, and the owner of ZNehr Coaching . He writes about everything related to bikes and endurance sports, from product reviews and advertorials to feature articles and pro data analytics. You can find Zach’s articles in Cyclingnews, Outside, Velo, TrainingPeaks, and more. You can follow Zach on Instagram  and  LinkedIn .

10Best Editors

USA TODAY 10Best provides users with original,...   Read More

USA TODAY 10Best provides users with original, unbiased and experiential travel coverage of top attractions, things to see and do, and restaurants for top destinations in the U.S. and around the world.

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Betting | Cubs vs. Mariners odds, prediction: MLB picks,…

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Betting | Cubs vs. Mariners odds, prediction: MLB picks, best bets for Friday, April 12

The Chicago Cubs continue their nine-game road trip Friday night as they open up a three-game set with the Seattle Mariners at T-Mobile Park.

For the most part, the Cubs have been tested in the early part of the season, facing contending teams like the Rangers, Dodgers and Padres.

Removing its 3-0 mark against Colorado, Chicago is just 4-5 against the three other foes after dropping two of three at San Diego earlier this week.

Let’s take a look at Chicago’s series opener ion Friday against the Mariners and find a betting edge.

Cubs vs. Mariners odds

• Run Line: Cubs +1.5 (-205), Mariners -1.5 (+168)
• Moneyline: Cubs +108, Mariners -126
• Total: Over 8 (-104), Under 8 (-118)

Odds via FanDuel

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Cubs vs. Mariners prediction

Left-hander Jordan Wicks makes his third start of the season for the Cubs.

Wicks, who has yet to pitch past the fifth inning this season, picked up a no-decision in his first outing at Texas as the Cubs blew multiple three-run leads in the first five innings.

Wicks put together four scoreless innings in his last outing against the Dodgers but gave up a pair of singles in the fifth inning before exiting the game.

Following a 2-6 road trip at Milwaukee and Toronto, Seattle returns home. The M’s needed extra innings to avoid the sweep against the Blue Jays on Wednesday.

Bryce Miller, who gets the nod for Seattle on Friday, struggled in his first start, allowing four runs in five innings of a 5-1 home defeat to the Red Sox.

However, the Seattle right-hander rebounded nicely in his last trip to the mound by tossing seven scoreless innings and striking out seven in a 5-3 victory at Milwaukee.

The offense needs to get on track for Seattle, which has scored a total of six runs in the first 27 innings at Toronto prior to busting out for five runs in the 10th inning on Wednesday.

The Cubs are 6-2 in the first five innings in their last eight games, while not allowing a run five times in the span.

Let’s back Chicago in the first five innings against the Mariners at plus-money.

• Pick: Cubs first five innings (+114, DraftKings )

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