The Best Day Trips from Chicago

Chicago is the heart of the Midwest and the third-largest city in the country. Its iconic skyscrapers rise over Lake Michigan, and it’s packed with museums, restaurants, theater, and other activities in its 77 distinct neighborhoods. 

But despite everything to do and see in the city, sometimes residents or visitors want a little break from the bustle, so they head to Wisconsin, Indiana, or Michigan, the more chill Midwest neighbors with sand dunes and hiking and unique cities of their own. Of course, there’s more to Illinois than Chicago, including day trips from the city to parks and historic sites. These 12 day trips from Chicago are all easy drives, but they have enough to do you that might consider staying overnight. 

Milwaukee, WI: 90 minutes by train, bus, or car

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Milwaukee is about a 1.5-hour drive from Chicago, but many Chicagoans prefer to take the Amtrak or Greyhound (no one wants to drive home after indulging in Wisconsin beers). Both also take about an hour and a half and drop you right in the center of Milwaukee. In the city, spend some time in the Historic Third Ward, full of decor and specialty shops, as well as bars and restaurants and the wonderful Milwaukee Public Market, a sampling of the city’s best food vendors and the perfect lunch spot. 

The Milwaukee Art Museum is one of the largest in the United States and also has one of the coolest designs, thanks to Spanish architect Santiago Calatrava. There’s also the Harley-Davidson Museum and its display of classic motorcycles, or the Milwaukee County Zoo, a great option for families. Of course, Milwaukee is famous for its baseball team, the Brewers, and for making lots and lots of beer. Tour Miller Brewery, Milwaukee Brewing Company, or Lakefront Brewery, or visit some smaller craft breweries such as Hacienda Beer Co, Eagle Park Brewing, or Third Space Brewing.

Lake Geneva, WI: 2 hours by car

Eighty miles from Chicago and one to two hours of driving, depending on traffic out of the city, the resort town of Lake Geneva is popular for its Gilded Age mansions, boutiques, spas, and golf courses. 

After the Civil War, wealthy Chicagoans started building mansions around Lake Geneva as summer homes. Many of them still exist today and can be seen via boat tours or on a walk along the Geneva Lake Shore Path. The 21-mile trail was originally used by the Potowatami tribe and later became a path for laborers working on the estates. Today, it’s a walking path open to the public, even as it goes right through some of the gardens of the estates. The Lake Geneva Public Library and Big Foot Beach State Park are popular starting points. 

Visit the Yerkes Observatory, known as the birthplace of modern astrophysics and operated by the University of Chicago Department of Astronomy and Astrophysics. A highlight is the 90-foot domed telescope, which, when visited at night, gives off a spectacular star show. 

Downtown, shop at galleries and antique shops such as Estate Art & Collectibles and sample local beers at Topsy Turvy Brewery, housed in a former cathedral. If you’re here for the golfing and spas, the AAA Four Diamond Grand Geneva Resort & Spa is the place to be with its two championship golf courses and high-end spa services. 

Galena, IL: 3 hours by car

Galena is about three hours from Chicago, but worth the trip for history lovers. Once a major port city on the Mississippi River, today it’s a tourist town with hundreds of buildings on the National Register of Historic Places, including the home of Ulysses S. Grant. Walk the historic Main Street, full of historic shops, hotels, and other buildings. Galena Cellars Vineyard and Winery has daily wine tastings, and Galena Brewing Company offers rotating brews made on-site. 

You can tour Grant’s home, which was built in 1859 and designed in the Italianate style by William Dennison. Galena residents gave the home to Grant as a thank-you upon his return from the Civil War. Today, the red brick home with green shutters holds the family’s original belongings, and a 30-minute tour takes you from the Civil War through Grant’s presidency. To really get into the history, take the 2.5-hour narrated Galena Trolley Tour through the historic district. 

In the winter, Galena is one of the only places in Illinois to ski. Get a day pass at the Chestnut Mountain Resort, which is also open in the summer for hiking or mountain biking. 

Madison, WI: 2.5 hours by car

Madison, with its lakes, food culture, university campus, and gorgeous capitol building, is one of the country’s best-kept secrets, and it’s only about 2.5 hours from Chicago. 

In the summer, take a loop around the farmer’s market—the largest in the US–and make sure to stop for Stella’s spicy cheese bread (the lines move quickly!). Pop into the Capitol for a free tour or to wander around yourself. The interior is made of 43 types of colorful stone, including Italian marble, Minnesota limestone, and Norwegian syenite. Make sure to look up from the center of the rotunda to view the beautiful “The Resources of Wisconsin” mural. 

From the Capitol, walk down pedestrian-only State Street and browse the local boutiques as you make your way to the University of Wisconsin campus, where you can sit on the colorful chairs (iconic) at the Memorial Union Terrace and sip Spotted Cow––a local beer only sold in Wisconsin. 

Throughout the city, there are parks and trails designed by famed landscape architect John Nolen and architecture by Frank Lloyd Wright. For an easy walk with lake views and to see more of campus, head from the Memorial Union to Picnic Point. 

Of course, Wisconsin is perhaps most famous for dairy. Sample cheese from around the state at Fromagination, get fried cheese curds at The Old Fashioned, watch ice cream be made and try some for yourself at the university’s Babcock Dairy Store, and be impressed at how Wisconsinites manage to put cheese in a truly astounding amount of dishes. As far as other food, you’ll want to try a traditional Wisconsin brat at State Street Brats, as well as check out some of the James Beard Award-winning chefs around the city. 

Oak Park, IL: 35 minutes by train 

Oak Park is just ten miles west of downtown Chicago but feels far away. The village is home to the Frank Lloyd Wright-Prairie School of Architecture District, a concentration of 27 Frank Lloyd Wright Homes, the largest in the country. Tour his home and studio, which was sort of an experiment for the architect and features hints at what would become his signature Prairie School Style. 

Oak Park was also home to Ernest Hemingway as a child. Visitors can tour the Ernest Hemingway Birthplace and Museum to learn about Hemingway’s time as a war reporter in Spain, see childhood photos, clips of his books that have been turned into movies, and more. In downtown Oak Park you can shop at local boutiques and bookstores and grab lunch or coffee at the numerous cafes and restaurants. Best of all, Oak Park is at the end of the CTA’s Green Line and easily accessible from downtown Chicago. 

Grand Rapids, MI: 3 hours by car 

“Beer City USA” is about three hours from Chicago, and the breweries are so good and so plentiful you might want to spend the night. Do a self-guided beer tour, making sure to stop at New Holland Brewing, Brewery Vivant, Harmony Brewing Company (which has excellent pizza), and the most famous, Founder’s Brewing (where the food is also good and there’s often live music on weekends). For a break from beer, try the ciders made with Michigan apples at Vander Mill Cider. 

Grand Rapids isn’t all drinking, though. The Frederik Meijer Gardens & Sculpture Park features works by Auguste Rodin, Ai Weiwei, and a horse sculpture designed by Leonardo da Vinci (one of two in the world), among gorgeous seasonal gardens. The Grand Rapids Art Museum downtown highlights Michigan artists, and the Gerald Ford Presidential Library and Museum tells the history of the 38th president, who was from Grand Rapids. Spend an hour walking through the Heritage Hill neighborhood, which has pretty homes, including several designed by Frank Lloyd Wright (you’re probably noticing this is a theme in the Midwest), cafes, shops, and a fantastic wine store

Lake Michigan Shore Wine Route: 90 minutes to 3 hours by car 

Michigan has been growing grapes since the 1860s, mostly Concord and Niagara grapes used in juice or jelly. In recent years though, the state has made strides in wine production and has won accolades for its rieslings, which rival those in the Finger Lakes in New York or even those in Germany. 

Massive Lake Michigan, sometimes referred to as an “inland ocean,” creates a growing climate unique to this part of the world. The Lake Michigan Shore Wine Route features 15 wineries that are part of the Lake Michigan Shore American Viticulture Area, as well as several tasting rooms. Pick a designated driver and head out for a day of wine tasting along the beautiful lakeshore. The wineries are an hour and a half to three hours away, depending on which you visit. Many of the wineries also serve food or are in towns like Saugatuck, with nice restaurants and cute downtown shopping streets. Don’t want to drive? There are plenty of bus tours from Chicago that stop along the route. 

St. Joseph and Benton Harbor, MI: 90 minutes by car or 105 minutes by train 

Neighboring towns St. Joseph and Benton Harbor can be visited together on a day trip from Chicago. About 1.5 hours from the city, they’re both cute beach towns where you can swim in Lake Michigan, visit historic lighthouses, and more. 

In St. Joseph, the Silver Beach Carousel is a must-do family attraction, while in Benton Harbor, adults might prefer a round at the Jack Nicklaus Signature Golf Course. Rent a boat and spend a day between the twin towns on the water, or relax on land at one of seven public beaches. Downtown, there are galleries and souvenir shops, and dozens of restaurants highlighting Michigan’s local fruits and vegetables. St. Joseph is also accessible via the Pere Marquette Amtrak line from Chicago, about an hour and 45-minute ride. 

Starved Rock State Park: 90 minutes by car

This park on the Illinois River is famous for waterfalls, steep sandstone canyons, and wooded trails. It feels a world away from Chicago, even though it’s only about 1.5 hours away. 

Grab a map from the visitor’s center and head off onto the trails. There’s something for every level, from flat paths where you can push strollers or wheelchairs to more challenging hikes that include a bit of scrambling up and down rock. In nearby Utica, try sparkling wines made with local varietals at Illinois Sparkling Wine Co. and have lunch at Lodi Tap House. 

Indiana Dunes National Park:  45 minutes by car

This peaceful coastline just 45 miles from Chicago was designated a national park in 2019. The main attraction is the huge, shifting sand dunes created by Lake Michigan’s wind and waves, but there are also wooded paths, wetlands, and prairies in the 15,000-acre park. With more than 50 miles of trails, there’s a hike for everyone, from sandy strolls to walks through the woodlands. 

Visit during migration season to see hawks, piping plovers, sandhill cranes, and more. Each year on the third weekend in May, the park plays host to a birding festival. You can also rent kayaks, take a horseback tour through the park, or just relax on the sandy beaches. 

House on the Rock, WI: 3 hours by car 

Truly one of the more bizarre attractions you’ll ever come across, but also the most fascinating, House on the Rock is great for people with kids. It’s located about three hours from Chicago, and like the name suggests, it is a house, or at least a complex of rooms, perched atop Shelter Rock. 

Owner Alex Jordan Jr. designed it to look like a Frank Lloyd Wright home, though it is said Wright, whose Taliesin home and studio is just down the road, hated House on the Rock. Inside, see Jordan’s collection of Titanic memorabilia, Venetian masks, dollhouses, mannequin angels, and more. There’s a 200-foot whale model, a reproduction of a Victorian-era street, and the world’s largest carousel. The main attraction is the Infinity Room, a long and narrow glass room that juts 250 feet into the air out from the rock the home sits on. Not for the faint of heart! 

Wisconsin Dells: 3 hours by car

It might seem strange that the self-proclaimed “Waterpark Capital of the World” is in a place that’s only warm a few months of the year, but if you make the three-hour drive from Chicago to the Dells, you’ll see that weather is not a deterrent. 

The city is part of the Dells of the Wisconsin River, a gorge formed by glaciers that makes for a gorgeous landscape and was the original reason for tourism in the area. Take a boat tour around the river to learn about the area’s geology and see some especially pretty spots only accessible from the water. 

Today, Wisconsin Dells is more famous for Noah’s Ark, a giant water park with thrilling water roller coasters, steep water slides, a wave pool, and more. If waterparks aren’t your thing, Mount Olympus is a more traditional theme park (though there are still some water rides). There’s also a downtown with mock German villages, kitschy souvenir shops, fudge and taffy stores, and plenty of restaurants. 

Visiting in the winter? No problem. The Wisconsin Dells has indoor waterparks, too, such as the Kalahari Resort, Chula Vista Resort, and Great Wolf Lodge, which all offer day passes. 

Best Chicago day trips to Michigan

• Grand Rapids
• St. Joseph & Benton Harbor
• Lake Michigan Shore Wine Route

Best Chicago winter day trips

• Grand Rapids: There’s plenty to do indoors, and the Frederik Meijer Gardens has a tropical conservatory to give you a taste of summer. 
• Milwaukee: Spend a day brewery and museum hopping, or rent some skates and go ice skating at Red Arrow Park. 
• Madison: Museums and restaurants provide a respite from the chill. Alternatively, do as Wisconsinites do and embrace cold weather with an ice fishing lesson or cross-country ski or snowshoe rental. 
• Galena: One of the only places in Illinois to ski, this historic town makes a fun winter getaway.
• Wisconsin Dells: Pretend it’s summer at one of the many indoor waterparks.

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