The Chicago Bucket List: 26 Things to Do When You Hit the Windy City

Heading off to the windy city soon?

Whether your trip is next week or you simply know that you want to go at some point, having a set list of things to do and see can help you make the most of the experience. With that said, you might need a little help creating a solid Chicago bucket list of sorts, and that's where we come in. Take some of these ideas to add to your own bucket list and have the Chicago trip of a lifetime:

Chicago Bucket List Ideas For Those Here for the Food:

Isn't half the fun of exploring any new city trying all the incredible foods the local area has to offer? Whether you're a connoisseur of five-star cuisine or prefer your meals to come from food trucks and other hidden gems, here are some food-related ideas for your Chicago bucket list:

  • First and foremost: try deep-dish pizza
  • Try the world-famous and ever-so-unique combo of caramel and cheese mix popcorn from Garret Popcorn Shop
  • Visit all the foodie neighborhoods of Chinatown, Greektown, Little India and Pilsen to taste a little of the world all in one city
  • Get a Chicago-style hotdog with seven toppings on it

chicago styled hot dog with fries: shutterstock. Homemade Chicago Style Hot Dog with Mustard Pickles Relish Tomato and Peppers

(via Shutterstock)
  • Try one of the city's Michelin-starred or James Beard Award-winning restaurants
  • Skip the Starbucks and try out a local small-owned coffee shop for your caffeine fix
  • Cool off and satisfy your sweet tooth with an Original Rainbow Cone

original rainbow cone in chicago: shutterstock. Rainbow cone on the Chicago side of Lake Michigan

(via Shutterstock)


Also read about: 13 Bucket List Ideas for You and Your Best Friend


Experience Chicago Culture With These Bucket List Ideas

There's a whole lot to do and see in Chicago other than just things that make your taste buds happy. Soak in the sights and a little culture while you're there with some of these Chicago bucket list ideas:

  • Visit Millennium Park and catch some live music while you're there
  • Attend Lollapalooza (the city's most famous music festival)
  • Or explore Grant Park when the festival isn't going on
  • Go on a public art tour
  • Be brave and stand on the all-glass balcony at Willis Tower's Skydeck Chicago
  • Or, if you're even braver, you can actually tilt over the city at the 360

360 chicago observation deck: john hancock building: shuttestock. Chicago, Illinois, USA - Aug 15, 2019: Tilting glass at John Hancock Center observation area

(via Shutterstock)
  • Chicago observation deck
  • See a comedy show
  • Or a live theatre show
  • Go to a live jazz or blues performance
  • Go back in time by visiting the Field Museum (and its many dinosaurs)
  • Check out the Adler Planetarium
  • Interact with the exhibits at the Museum of Science and Industry
  • Go to the Art Institute of Chicago
  • See the sights from a different perspective by taking a river cruise
  • Go for a long stroll on the 18-mile Lakefront Trail
  • Explore the urban jungle that is the Lurie Gardens
  • Find one of the city's many secret gardens, like the ones in Lincoln Park and Jackson Park
  • And, of course, take a selfie at "The Bean" (officially titled Cloud Gate, by the way)

chicago: the bean, cloud gate. shutterstock. CHICAGO, ILLINOIS/USA-OCTOBER 13 2018: image of the Cloud Gate or The Bean in the morning October 13 2018 in Millennium Park, Chicago, Illinois

(via Shutterstock)


Also read about: The Bucket List: 34 Things You Should Do While You're Still a Teenager


There's a whole lot to see and do in Chicago, and we can only hope that these ideas help you craft a perfect city bucket list of your own. But if the Big Apple is a little more your style, don't worry, we've got you covered on that one too. Click HERE to check out the ultimate NYC bucket list.