The 17 best road trips from Chicago

Driving time from Chicago: Four and a half hours

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 in Springfield to see attractions like the Illinois State Capitol, or in Atlanta, IL to take a photo with Paul Bunyon holding a massive hotdog. 

Driving time from Chicago: Five hours

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. 

Driving time from Chicago: Five hours

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. 

Driving time from Chicago: Four and a half hours

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 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. 

Driving time from Chicago: Three hours

At the top of many Chicagoans city escape must-visit list is Galena, Illinois. This charming town just under three hours from the city is known for its history, 19th-century architecture and resorts. There are hundreds of unique and antique shops in the city center to add some vintage pizzazz to your living room. History buffs can head over to the Ulysses S. Grant Home to tour the city’s proudest attraction. Once you’ve worked up an appetite, stop into Log Cabin Steakhouse, which has been in operation since 1937. During the third weekend of June, tourists and locals alike gather for the annual Great Galena Balloon Race.

Driving time from Chicago: Four and a half hours

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. 

Driving time from Chicago: Five hours

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 over 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

Driving time from Chicago: Three hours

Sure the Midwest loves its college towns, but Madison's proximity to five surrounding lakes make it one of the more of the scenic ones. The abundance of waterways make kayaking, rafting and canoeing especially popular—you can book them directly through Madison Boats. For those averse to using their sea legs, there's the 16-acre Olbrich Botanical Gardens for all ages or the National Mustard Museum (yes, you read that correctly). It wouldn't be a trip to Wisconsin without trying blocks and blocks of cheese, so make sure to stop by the "Capital of Cheese" known as Fromagination in downtown Madison. 

Driving time from Chicago: Five hours

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.

Driving time from Chicago: Six hours

Not going to make it to Napa this year? Opt for the just-as-beautiful Shawnee Hills Wine Trail instead. The 35-mile scenic drive meanders through Shawnee National Forest in southern Illinois and features over 10 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. 

Driving time from Chicago: Two and a half hours

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. From hiking the Saugatuck Dunes to window shopping on Butler Street to 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. 

Driving time from Chicago: Four hours

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 plethora 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). 

Driving time from Chicago: Four hours

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.

Driving time from Chicago: Two hours

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. 

Driving time from Chicago: Five hours

There's a surprising amount to explore over 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.

Driving time from Chicago: Three and a half hours

In the heart of Southern Indiana, Columbus is an unexpected center for boundary-pushing architecture—in fact, the American Institute of Architects ranked the city sixth in the nation for architectural innovation. Roughly 70 different constructions sprinkled around the city and county make this city an architectural wonder. Take an Architectural Highlights Tour of more than 30 of Columbus' structures and learn how this city became the state's award-winning arts and design destination. Make another pit stop of striking constructions with a stroll through Mill Race Park, an 85-acre riverfront park near the city's center. Once you’ve worked up an appetite, stop by Columbus Bar, the oldest bar and restaurant in town.