Not only is Chicago an exciting city to be in, but there are also lots of captivating places nearby to explore that are just a short drive away. Located in the northeastern corner of Illinois, you can easily take day trips to other cities, small towns, and natural areas in Wisconsin, Michigan, Indiana, and Downstate Illinois. So, next time you need a break from the city or just want to get to know this part of the Midwest a bit better, check out these day trips from Chicago.

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Holland, Michigan Authentic Dutch windmill in Holland Michigan with spring tulips
Authentic Dutch windmill in Holland Michigan with spring tulips

Holland, Michigan (Hotel Prices & Photos)

The city of Holland, Michigan is only about two hours and 15 minutes from Chicago, making it a perfect destination for a day trip. This town is inspired by the Netherlands and still retains a historically Dutch heritage today. Here you can walk through tulip gardens, see windmills, and slow down your pace of life for the day. Early May is a popular time to visit because this is when the Tulip Time Festival takes place with food, parades, music, and dancing. The famous New Holland Brewing is also here for your post-sightseeing and post-shopping refreshment. If you don’t want to drive or have a car, you can also reach Holland by train from Chicago in about three hours.

Madison, Wisconsin Madison, Wisconsin
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Madison, Wisconsin

Madison, Wisconsin (Hotel Prices & Photos)

Within about three hours, you can get to Madison, Wisconsin from Chicago and experience a refreshing change of pace from big city life with tons to see and do. This is a college town known for its top-notch cheese and beer, and it’s also a very bike-friendly city that’s fun to explore on two wheels. There are a couple lakes here where you can paddle, the state capitol building you can tour, and lots of arts and culture sites where you can attend a live performance or check out a festival.

Starved Rock State Park, Illinois Waterfall at Starved Rock State Park
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Waterfall at Starved Rock State Park

Starved Rock State Park, Illinois (Hotel Prices & Photos)

Anyone who says that Illinois doesn’t have stunning outdoor landscapes clearly hasn’t been to Starved Rock State Park! This park is an outdoor lovers’ dream destination with plenty of hiking, rock climbing, ice climbing, and camping to keep you busy for an entire weekend. But at just about an hour and a half by car, it’s also the perfect distance away for a day trip. Starved Rock has some truly impressive rock formations, waterfalls, and canyons, and it’s near the town of Oglesby, Illinois. You can also take a rafting trip on the Vermillion River and stay overnight at the Starved Rock Lodge if you have more than a day to spend here.

Indiana Dunes National Lakeshore, Indiana Indiana Dunes
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Indiana Dunes

Indiana Dunes National Lakeshore, Indiana (Hotel Prices & Photos)

You only have to drive about an hour for your day trip if your destination is the Indiana Dunes National Lakeshore. This natural wonder includes a 15-mile beach along Lake Michigan with impressive dunes and plenty of opportunities for outdoor recreation. You can rent a sandboard at a nearby shop and try sandboarding down the dunes just for fun. This is also a prime area for horseback riding along the beach and getting some serious exercise while hiking up and down the dunes. Other things to do here include cross-country skiing in the winter, bird watching during migration periods, and taking the kids to the Nature Play Zone at the Paul H. Douglas Center.

Lake Geneva, Wisconsin View of Lake Geneva in the fall Wisconsin
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View of Lake Geneva in the fall Wisconsin

Lake Geneva, Wisconsin (Hotel Prices & Photos)

Lake Geneva is a beautiful destination just north of the Wisconsin border and about an hour and a half from Chicago by car. This has been a favorite destination among Chicago-area families for generations and is situated on a lovely eight-square-mile lake. Come here for summertime fun out on the water or to get some exercise on the 21-mile Geneva Lake Shore Path. This is a popular destination for Chicago-area weddings and has lots of quaint restaurants and inns to stay at if you have more than a day to spend here.

St. Louis, Missouri Gateway Arch
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Gateway Arch

St. Louis, Missouri (Hotel Prices & Photos)

If you’re up for a longer drive, about four and a half hours, you can also visit St. Louis, Missouri by taking Interstate 55 from Chicago. St. Louis is known for the famous Gateway Arch but also has lots of great authentic barbecue restaurants to check out if you’re a meat lover, while the Missouri Botanical Gardens and Forest Park offer plenty of outdoor recreation. Make a pit-stop in Bloomington, Illinois, which is about your halfway point on the drive, for a bite to eat and to stretch your legs on this day trip.

Milwaukee, Wisconsin Milwaukee
Milwaukee

Milwaukee, Wisconsin (Hotel Prices & Photos)

Milwaukee is another Wisconsin city that’s great for a day trip from Chicago, especially if you enjoy great food and beer. The drive is only about an hour and a half, or alternative, you can hop on an Amtrak train from Chicago for some car-free exploration. Here you’ll find lots of great vendors selling everything from seafood to chocolate and more at the Milwaukee Public Market and many breweries for tasting local craft beer. Its also fun to bring your own kayak or rent one in Milwaukee to paddle down the river and dock at bars and restaurants along the way when you need a break with tasty refreshments. In Milwaukee, you can also check out the Harley-Davidson Museum tours or attend one of the city’s many summer festivals.

Grand Rapids, Michigan Architecture of Grand Rapids Michigan
Architecture of Grand Rapids Michigan

Grand Rapids, Michigan (Hotel Prices & Photos)

The city of Grand Rapids in Michigan is also about a three-hour drive away and a prime spot for art lovers and craft beer fans. This is a beautiful place to come in the spring and fall seasons to witness the turning leaves and changing seasons. Top breweries in town to check out are Founder’s Brewing and Brewery Vivant, but there are dozens more to stop by if you love beer and if you’re not driving!

Devil’s Lake State Park, Wisconsin Rocks at Devils Lake State Park
Credit: Alyssa L. Ochs
Rocks at Devils Lake State Park

Devil’s Lake State Park, Wisconsin (Hotel Prices & Photos)

If epic outdoor recreation is what you seek for your day trip from Chicago, then definitely consider Devil’s Lake State Park. Near Baraboo, Wisconsin, this is the top rock climbing destination in the Chicago area and great for hiking, boating, paddling, and swimming too. There are also campgrounds nearby and in the park too if you have more than a day to spend here.

Indianapolis, Indiana Indianapolis, Indiana
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Indianapolis, Indiana

Indianapolis, Indiana (Hotel Prices & Photos)

Within three hours of Chicago, you can also take a day trip to the city of Indianapolis, which is an ideal destination for families with kids. The children’s museum here is one of the best in the world, and the Indianapolis Motor Speedway is a large and impressive racetrack for car lovers. You can also check out White River State Park for some time in the outdoors.

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