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How to Get the Most Fun Out of a Day Trip from Chicago
August 5, 2022

How to get the most fun out of a day trip from Chicago

Chicago is one of the most popular tourist destinations in the United States, with a wide range of attractions to entertain visitors. The city's unique natural features include beaches, forests, lakes and rivers. Chicago is also home to some of America's most iconic architecture, including the Willis Tower (formerly known as Sears Tower), John Hancock Center and the Wrigley Building. 

In addition to all of the attractions in the city, Chicago is surrounded by amazing sights and adventures in towns a short drive away. If you're in the mood for a drive or to explore some of the top nearby destinations, this list will get you started in the right direction.

Best Day Trips Near Chicago

Chicago could easily keep you busy for days. But if you’re in the mood for a drive or to explore some of the top nearby destinations, this list will get you started in the right direction.

House designed by Frank Lloyd Wright in Oak Park, Illinois

Oak Park, Illinois

10 miles (30-minute drive) from downtown Chicago

Oak Park is so close to Chicago that you can reach it via train (the Green and Blue Lines on CTA and the Union Pacific/West Line on Metra). For art lovers and architecture fans, Oak Park cannot be missed. It is home to more Frank Lloyd Wright buildings than anywhere else in the world. Famed American novelist Ernest Hemingway also grew up here and you can visit the Ernest Hemingway Birthplace Museum to see where he was born and learn more about the people who helped shape his life.

Indiana Dunes National Park

50 miles (1-hour drive) from downtown Chicago

Indiana Dunes National Park is one of the nation's newest national parks and one of the most scenic spots in the Midwest. It stretches for 15 miles along Lake Michigan and is home to dunes, marshes, prairies and forests. Spend the day at the beach, go boating, lace up for hiking trails or go horseback riding on the park’s equestrian trails. 

Lake Geneva, Wisconsin

82 miles (90-minute drive) from downtown Chicago

Lake Geneva offers a year-round respite from the hustle of urban living with numerous outdoor activities along beautiful Geneva Lake. This city is full of outdoor adventures including zip lining, taking a scooter tour, or even visiting a safari. For a day on the water, Riviera Beach is popular for swimming, sunbathing and boating. 

Milwaukee, Wisconsin skyline at dusk

Milwaukee, Wisconsin

92 miles (1 hour, 40 minute drive) from downtown Chicago

Milwaukee is home to the famous Miller Brewery, as well as numerous microbreweries and eateries serving up local craft beers. There are so many things to do in this city including golf courses, theaters, 150 parks and the Harley Davidson Museum, which has displays of classic motorcycles, including one from Elvis Presley. Milwaukee is known as the “City of Festivals,” as it is home to scores of events and celebrations throughout the year, including food festivals, car shows, cultural fairs and music festivals like Summerfest, which spans over three weekends and features 12 stages of live performances. 

Starved Rock State Park, Illinois

93 miles (1 hour, 43 minute drive) from downtown Chicago

This state park is free to enter and attracts millions of visitors each year. Pre-register to join a free guided hike from June to November, or go on your own and enjoy 13 miles of well-marked trails that pass by waterfalls and 18 canyons that offer amazing views of the Illinois River. 

State capitol building in Madison, Wisconsin

Madison, Wisconsin

147 miles (2 hour, 39 minute drive) from downtown Chicago

Madison is the state capital of Wisconsin and is known for a large selection of craft beverages. It’s also home to the University of Wisconsin-Madison. Madison is consistently selected as being one of the best cities to live in based on education and job availability. One of the city’s most popular attractions, the Olbrich Botanical Garden is a 16-acre indoor and outdoor garden area that is filled with tropical plants, birds and even a waterfall. 

Holland, Michigan

152 miles (2 hour, 24 minute drive) from Chicago

This small town just inland of Lake Michigan is known for its Dutch heritage and celebrates it through food, cultural activities and annual events. Visit in the spring to see magnificent views of more than 4.5 million tulips in the gardens across the city. 

Avail can get you there

Need a car for your day trip from Chicago? Instead of renting a car, borrow with Avail. Reserve your car online and pick it up in neighborhoods across the city. Insurance and 24/7 roadside assistance are included so you can enjoy your trip and the open road stress-free.