Menu

THE ULTIMATE CHICAGO BUCKET LIST

Take the prerequisite Bean selfie, conquer the giant Ferris wheel, say hi to a Titanosaur — and whatever you do, come hungry!

Build your Chicago itinerary with this bucket list of things to eat, drink, see and do. These are the classics. The essentials. But by no means does our bucket list cover all that the city has going on. You could stay here for days, weeks, months...and STILL not get to everything.

This, though, is a great place to start. 

EAT UP & DRINK IN THE CITY

Chicago Bucketlist | Food & Drink

Eat

Drink

GO WIDE-EYED FOR CULTURE

Chicago Bucketlist - Arts and Culture

Sounds

Exhibits

Shows

  • Sit in the "Splash Zone" at Blue Man Group (waterproof ponchos provided — which says everything!)
  • Spring for the best seats in the house at a Broadway in Chicago show
  • See Chicago's very own talent shine at one of 5 Tony Award-winning theaters: Steppenwolf, Goodman, Victory Gardens, Lookingglass and Chicago Shakespeare — take your pick!
  • Grab a seat at The Yard, a bold new theater space with movable towers for the most contemporary theater-going experience out there. Chicago Tribune has even hailed it as "The Greatest New Theater in the World"!
  • Enjoy experimental and avant-garde theater lakeside (and year-round) at the new and improved Theater on the Lake

BE WOWED BY CITY SIGHTS 

Chicago Bucketlist - Tours and Attractions

Thrills

  • Set yourself a 1,353-foot challenge: The Ledge (glass floor and all) at Skydeck, Willis Tower  
  • TILT over the city at 360 Chicago observation deck
  • See fireworks and a 196-foot Ferris wheel rule the skies at Navy Pier all year round.
  • Hover above the city and lake in your very own piloted helicopter

Jaunts

Sights

  • Take in "landscape art under glass" at Garfield Park Conservatory, one of the largest conservatory's in the country
  • Watch a light and water show on summer nights at Buckingham Fountain (jets shoot to a height of 150 feet!)
  • Paddle alongside spewing, larger-than-life Chicagoans at Millennium Park's Crown Fountain 
  • Count the building fragments embedded in the Tribune Tower facade (there's a little bit of the Taj Mahal, Parthenon and Palace of Westminster in Chicago!)
  • And, of course, take a selfie with #TheBean (aka Cloud Gate

SOAK IN THE GREAT OUTDOORS

Bucket list

Sports

Activities

  • Grab your skateboard and BMX bike and head to Grant Skate Park —  multi-skill-level concrete ramps, grinding rails and handrails, bench seating and native landscape plantings, all with a view of the lake and city.
  • Work up a sweat (or catch a sunrise) along the Lakefront Trail
  • Scale a 40-foot climbing wall with views of the lake and city skyline, or rollerblade "the ribbon" at Maggie Daley Park
  • Bike, skate, walk, run -- and take in a little hipster culture along The 606  
  • Paddle through an architectural canyon on a river kayak - and soak up the award-winning Chicago Riverwalk 

Relaxation

  • Lose yourself in the Lurie Gardens — with the Art Institute of Chicago Modern Wing and city skyline as your reference
  • Take some artsy pics at the tortoise shell-like South Pond pavilion -- right in the middle of Lincoln Park Zoo's "urban ecology" 
  • Find Lincoln Park's hidden garden: Alfred Calder Lily Pool. Sit in the pavilion, gaze upon the prairie plantings and listen to the songbirds sing. Ahh
  • Catch a tan or a quick volleyball game at one of Chicago's lakefront beaches 

Explore more: That's a lot of itinerary inspiration! Want to start with a ready plan? Try this 2-Day Chicago Guide for first-time visitors or pick an 'L' stop and go sightseeing along the train route.

Also check out,

Featured Partners