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 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!
Activities
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
Seasonal
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
Cultural
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
Food
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
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 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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