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Chicago Bucket List: 65+ Best Things to Do in Chicago

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Ultimate Chicago Bucket List

Looking for the best things to add to your Chicago bucket list? Here are 65+ ideas for the best things to do in Chicago to make the most out of this amazing city.

Chicago Bucket List

Chicago is one of the top cities in the United States, and it truly offers something for everyone.

Whether you’re interested in food, sports, outdoor activities, culture, art, or history, you’ll never be bored in Chicago. This Chicago bucket list is perfect whether you live in Chicago or you’re just visiting.

(And if you’re just visiting Chicago for a short time, it’s true that you won’t be able to do everything on this list, but that just gives you an excuse to plan another trip back!)

Ready for the can’t-miss Chicago things to do?

Here are the best Chicago bucket list ideas to make the most out of the Windy City!


Chicago Bucket List



Chicago has activities for everyone. Yes, some of these are extremely touristy, but they’re popular for a reason and they all guarantee a memorable experience.

Snap a photo in front of the Bean

Get a bird’s eye view of the city from Willis Tower

Spend an afternoon at Navy Pier and ride the Ferris Wheel

Wander through the Lincoln Park Zoo

Recreate the events of Ferris Bueller’s Day Off

Go for a boat ride on Lake Michigan

Explore the city on a bike tour

Go kayaking in the Chicago River

Watch the Chicago bulls play at United Center

See a comedy show at The Second City

Take a helicopter tour over the city

Watch the lights show at Buckingham Fountain

Take a walk on the 606

Grab a drink on the Chicago Riverwalk

Visit the 360 Chicago Observation Deck at night

Stroll through the Garfield Park Observatory

Cycle along Lake Michigan’s Lakefront Trail

Ride the Chicago water taxi





Chicago has plenty of year-round activities, but there are some things you can only do depending on the season. These are some of the best seasonal bucket list ideas for Chicago.

Catch a Chicago Cubs game at Wrigley Field in the summer

Celebrate St. Patrick’s Day the Chicago way

Admire the holiday lights at Lincoln Park Zoo

Attend Lollapalooza or another summer music festival

Check out the Christmas Lights at the Chicago Botanical Garden

Watch the Chicago Air & Water Show in the summer

Go ice skating in Maggie Daley Park

Admire the fall colors at Morton Arboretum

See the Millennium Park Christmas tree

Stroll through the Christkindlmarket in Daley Square

Get spooky at the Night of 1,000 Jack-o’-Lanterns at the Chicago Botanical Garden

Enjoy free live music at the Millennium Park Summer Music Series

Attend the Chicago Thanksgiving Day Parade

Take a Chicago ghost tour around Halloween


Chicago Bucket List



Being the third largest city in the United States, Chicago is a cultural hub. You’ll find no shortage of world-class museums, entertainment, and other cultural offerings.

Admire the collections at the Art Institute of Chicago

Catch a show at the Chicago Theatre

Get lost wandering the Field Museum of Natural History

Watch a performance at the Chicago Symphony Orchestra

Seek constellations at the Adler Planetarium

Take a public art walking tour

Listen to live blues music at Buddy Guy’s Legends

Visit Frank Lloyd Wright’s Oak Park home

Tour the Robie House in Hyde Park

Attend the Chicago Jazz Festival in September

Catch a jazz show at The Green Mill

Check out the Museum of Science and Industry

Take an architectural river cruise

Visit the Museum of Contemporary Art


Chicago Bucket List



Chicago is famous for its food scene, and with good reason. No Chicago bucket list would be complete without eating your way through the city’s best culinary creations…

Try one of the dozen plus Michelin starred restaurants in Chicago

Get your Greek on in Chicago’s Greektown

Take a Chicago food tour

Eat your way through Chicago’s deep dish pizza offerings

Try an Italian beef sandwich

Go out for dim sum in Chinatown

Pile on the toppings on a Chicago-style hot dog

Check out one of the Chicago’s 70+ craft breweries

Attend the Taste of Chicago food festival in July

Try ice cream at The Original Rainbow Cone

Enjoy authentic Mexican food in Pilsen


Indiana Dunes National Lakeshore, Indiana, United States of America


Day Trips

Chicago is in a great location with tons of options for day trips just a couple hours away. Here are some of the best Chicago day trips to add to your Chicago bucket list:

Check out the craft beer scene in Milwaukee, Wisconsin (1.5 hours by car or train)

See the Dutch-inspired town of Holland, Michigan and its famous Tulip Time Festival (2.5 hours by car)

Enjoy the resort town of Lake Geneva, Wisconsin (1 hour and 40 minutes by car)

Spend a day in the architecturally signifiant suburb of Oak park (35 minutes by train)

Visit Grand Rapids, Michigan during ArtPrize (3 hours by car)

Relax in nature at Indiana Dunes National Park (1 hour by car or train)

Take in the breathtaking canyons and waterfalls at Starved Rock State Park (1.5 hours by car)

Explore nature at the Morton Arboretum (25 minutes by car)


Chicago Bucket List


Chicago Bucket List Ideas

These are the best Chicago bucket list ideas to help you make the most out of the city.

No matter what you’re interested in, Chicago has something for everyone. Take advantage of all this awesome city has to offer with these top Chicago bucket list ideas!

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