5 popular U.S. cities close to Chicago

When you’re hankering to take a road trip, sometimes the destination is actually just as important as the journey. If Chicago is your starting point and you’re unsure of where to go, you’ve come to the right place. There are a number of exciting cities close to Chicago that each offer a different flavor of the Midwest and may even provide a scenic drive to enjoy on the way. We’ve narrowed down the options to five that are sprinkled around neighboring states. Each one has its own unique attributes, which should make it a little easier for you to choose where to go.

1. Minneapolis, Minnesota

Distance from Chicago to Minneapolis: 409 miles (6 hours and 15 minutes)

You’ll enjoy a calm, scenic drive when you go from Chicago to Minneapolis, which is perfect for a road trip with family or a few friends. Once you arrive, one of the standout experiences you can have here is exploring historic districts where the city’s unique past serves as a backdrop for modern shops, restaurants, art galleries and cultural venues.

Start your itinerary in the Mill District. Facing north at the Mississippi River, you’ll see the Stone Arch Bridge, which looks plucked right out of a small European village. This piece of history was completed in 1883 as a railroad crossing over the river, and it now serves as a pedestrian and biking bridge. Back in the Mill District is the heart of Minneapolis’ past. Not long after its founding in the 19th century, the city became the hub of the flour milling industry. Today, those former mills are home to a number of businesses and even residences. Don’t miss the Mill City Museum, hosted inside the former Washburn “A” Mill; Mill Ruins Park, where you can see an archaeological excavation of this historic site; and the Mill City Farmers Market on Saturdays from May to October and every second Saturday from November to April, which is set up in an old rail yard for the mills.

About a mile and a half north along the river is the Minneapolis Warehouse Historic District, which is on the National Register of Historic Places. This area has also been revitalized, with former 19th- and 20th-century warehouses transformed from pieces of the past to vibrant spaces to eat, work and play. Don’t miss a live show at historic music venues First Avenue and 7th St Entry; the Instagrammable five-story Bob Dylan Mural in the Hennepin Theatre District; and a Minnesota Twins game at Target Field during baseball season.

2. South Bend, Indiana

Distance from Chicago to South Bend: 96 miles (1 hours, 45 minutes driving)

It’s certainly reasonable to assume that most people making the drive from Chicago to South Bend are headed to the University of Notre Dame, especially during football season when the Fighting Irish are playing at home. Although it may get rowdy on campus, South Bend itself is one of the best cities close to Chicago for families to visit. 

Curious kids will love the variety of museums on offer here. Start at the South Bend Chocolate Company, where you can go behind the scenes with a factory and museum tour — tasty treats included. Then head to the Studebaker National Museum to browse the antique car collection. Just around the corner is The Oliver Mansion. Walk through 2.5 acres of landscaped gardens and explore the mansion’s 38 elegant rooms, which have been preserved with original furnishings from when the Oliver family lived there starting in 1897. Don’t miss the Worker’s Home, where you can learn about the community’s African American history.

When the kids need to stretch their legs or get some energy out, Howard Park is the perfect destination. There’s a playground, events center, biking trail, ice skating trail and pond (late November through March) and more. Events are hosted on the festival lawn throughout the year, including concerts and performances, outdoor yoga, arts classes and artisan markets. 

If you have older kids who love a thrill ride, take them to tackle the rapids at East Race Waterway, a 1,900-foot artificial white water course right in downtown South Bend. East Race Waterway is only open on Saturdays and Sundays between June and mid-September, and everyone in the raft has to be at least 54 inches tall, so measure your kids’ heights before you decide to go.

3. Lake Geneva, Wisconsin

Distance from Chicago to Lake Geneva: 83 miles (1 hours, 45 minutes driving)

Nowadays, Lake Geneva is a favorite getaway destination for outdoor and adventure enthusiasts. But if you roll back the clock, its history is an interesting one. The area was covered by glaciers until around 18,000 years ago. Then it was inhabited by native tribes for centuries before pioneer settlers drove them out in the 1830s. After the civil war, Lake Geneva began to attract deep-pocketed Chicagoans who built mansions on Geneva Lake to serve as their summer homes. It was this influx of money that built Lake Geneva into the resort town that it is today. Before you don your bathing suit and get out on the water, stop by the Geneva Lake Museum to learn even more about the town’s history.

Once you understand the facts, you’ll be able to better appreciate the natural beauty and historic buildings around this area. One of the best ways to see it all is by going sky high in a hot air balloon. Or if a fear of heights is keeping you grounded, hit the hiking trails, take a scooter tour around the lake or enjoy a guided trail ride on horseback. Of course, there are plenty of activities on the water too. You can join a laid-back cruise, charter a fishing boat or explore on your own by renting a boat, kayak or paddle board. 

Of course, as a resort town, Lake Geneva also offers plenty of ways to pamper yourself. Luxury resorts, waterfront inns and boutique hotels offer comfortable accommodations filled with amenities, as well as spa treatments, upscale dining and even weekend wellness retreats. It’s no surprise that many also make the escape from Chicago to Lake Geneva for a romantic getaway.

4. Milwaukee, Wisconsin

Distance from Chicago to Milwaukee: 92 miles (1 hours, 40 minutes driving)

There is certainly no shortage of cultural, educational and physical activities in Milwaukee, like the Harley Davidson Museum, Mitchell Park Horticultural Conservatory and walking tours of historic sites. But of the cities close to Chicago, what this one does better than most is brew beer, and a big variety of it. Milwaukee is well-known for its suds, both small-batch craft and mass-produced.

So after driving from Chicago to Milwaukee, park your car and leave it there for the duration of your stay. Make your way to local breweries on your own two feet, by rideshare or public transportation, or by joining a specialized tour group, of which there are many. 

The hardest part will be figuring out where to go since there are well over a dozen options. You could create a strategy of just visiting taprooms for a flight or choose breweries based on the tours they offer. Lakefront Brewery, for example, offers a 45-minute tour every day of the week that includes four 8-ounce pours and a souvenir pint glass in the ticket price. If you’re into experimental beers, Good City Brewing has small-batch productions and an extensive food menu for when you inevitably get peckish (do not miss out on the cheese curds!). Over at MobCraft, you can find wild sours and even crowdsourced beer. That’s right, each year they crowdsource recipe submissions, have the public vote online and then brew the winner.  

Even if you consider yourself a beer snob, you should still consider taking a tour of the Miller Brewing Co. and Pabst Brewing Co. facilities. These tours are really well done, taking you through the history of the companies and the brewing process over the course of about an hour. Plus, you’ll get a beer sample included in your tour ticket.

5. St. Louis, Missouri

Distance from Chicago to St. Louis: 297 miles (4 hours, 30 minutes driving)

St. Louis is one of America’s great musical cities, but there’s one genre in particular that it’s known for: the blues. Music is part of the fabric of the city, having been brought to St. Louis from the South during the Great Migration in the early 20th century. Before you pop into a venue for live music, stop at the National Blues Museum, which is just down the street from the city’s iconic Gateway Arch and a short walk from the Mississippi River, serving as the natural border between Illinois and Missouri. Exhibits at the National Blues Museum explain the origin and evolution of the blues, introduce visitors to the genre’s trailblazers and legends, and engage your senses by allowing you to create your own blues song.

Once you have a solid understanding of the blues and its meaning within St. Louis and beyond the city limits, it’s time to experience it live. There are plenty of venues around town, including BB’s Jazz, Blues & Soups; Broadway Oyster Bar; Hammerstones; Blue Strawberry; Evangeline’s; and The Dark Room. If you decide to drive from Chicago to St. Louis in the spring, summer or fall, try to time your trip around one of the city’s annual blues festivals. The Gateway Blues Festival is held in April, the Soulard B3 Festival happens in May, Blues at the Arch is in August, and both Music at the Intersection and Old Webster Jazz and Blues Festival are in September.  

Get there with Avail

When you’re ready to visit one of these great cities close to Chicago, book your road trip car with Avail. We have dozens of self-service locations in neighborhoods across Chicago to make pick-up and drop-off convenient to where you live, work or are staying. Every trip is protected by Allstate insurance and 24/7 roadside assistance. And there are no extra fees to add a second driver and share the driving responsibilities. You’ll pay less and get more when you book a rental car with Avail.