The Ultimate Chicago Bucket List


This definitive list includes the essential Chicago musts, from iconic attractions to award-winning restaurants.


* Eat Chicago-style pizza…and lots of it!  Deep dish and thin crust, alike

* Pile seven toppings on a hot dog… it’s the Chicago way

* Devour handfuls of the caramel-and-cheese mix from world-famous Garrett Popcorn Shop

* Learn the lingo before you order an Italian beef sandwich

* Taste the world in our foodie neighborhoods: Chinatown, Greektown, Pilsen, Little India, and more

* Tackle a prime cut at Chicago’s steakhouses — both legendary and new

* Embark on an epicurean adventure at Michelin-star restaurants and James Beard Award winners

* Savor summer with a colorful scoop—Chicago’s own Original Rainbow Cone

Experience Chicago’s music

* Pack a picnic and catch live music at Millennium Park free summer music series

* Hear blues master Buddy Guy play live at Buddy Guy’s Legends

* Discover the next Bill Murray or Tina Fey at The Second City

* Relive the Jazz Age at the historic Green Mill Jazz Club in Uptown (it first opened in 1907 and was a favorite of Al Capone)

* Hear living legends (for free!) at the Chicago Jazz Festival and Chicago Blues Festival

Explore our must-see museums

* Gaze up at a Titanosaur, the largest creature known to man, at the Field Museum and say hi to SUE, the most complete and best preserved T.rex ever discovered

* Explore the Art Institute of Chicago, Ferris Bueller-style to see one of the largest collection of Impressionist art outside the Louvre

* Stand in a tornado, inside a U-boat, or deep down in a coal mine at the interactive Museum of Science and Industry

* Watch rare and local aquatic creatures in stunning habitats at the Shedd Aquarium

* Marvel at the wonders of the universe at Adler Planetarium, the first planetarium in the Western Hemisphere

* See remnants of the Great Chicago Fire and hop on the first ‘L’ car at the Chicago History Museum


* Sit in the “Splash Zone” at Blue Man Group (waterproof ponchos provided)

* Get tickets for a show at Broadway in Chicago or any of our 200+ theaters

* Discover up-and-coming talent at cutting-edge neighborhood theaters

* Enjoy experimental and avant-garde theater lakeside at the stunning Theater on the Lake


* Stand outside one of the world’s tallest buildings at The Ledge, an all-glass balcony at Willis Tower’s Skydeck Chicago

* TILT over the city at 360 CHICAGO observation deck at the former John Hancock Center

* See fireworks and a 196-foot Ferris wheel rule the skies at Navy Pier


* Get up close and personal with art masters—from Caldwell to Miró to Picasso—on a public art tour around the city

* See Chicago’s most iconic architecture on an architecture boat cruise, like the Chicago Architecture Foundation Center River Cruise

* Visit Chinatown in a water taxi—and indulge in more than a little dim sum


* Watch a light and water show on summer nights at Buckingham Fountain (with jets shooting to a height of 150 feet)

* Splash alongside 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)

* Take in “landscape art under glass” at Garfield Park Conservatory, one of the largest conservatory’s in the country

* Gaze up at Chicago’s famous Marina City towers (aka the corncobs), featured in everything from movies to album covers

* And, of course, take a selfie with Cloud Gate, aka “The Bean”

Urban adventures

* Go for a waterfront stroll through sandy beaches and green space on the 18-mile Lakefront Trail

* Go ice skating or scale a climbing wall at Maggie Daley Park

* Bike, skate, walk, run—and take in a little artsy culture along The 606

* Paddle through an architectural canyon on a river kayak—then grab a drink on the award-winning Chicago Riverwalk

* Explore beautiful Grant Park, home of top city events like Lollapalooza and Taste of Chicago

* Catch a tan or a quick volleyball game at one of Chicago’s lakefront beaches

City in a garden

* Lose yourself in the Lurie Gardens with views of the city skyline

* Stroll the nature boardwalk around the stunning South Pond in Lincoln Park Zoo

* Visit an authentic Japanese garden hidden away inside Jackson Park

* Find Lincoln Park’s secret garden, the secluded Alfred Caldwell Lily Pool

Planning a future trip to Chicago?  Experience the city’s famous attractions at a 50 percent savings with Chicago CityPASS.  Take your time and enjoy each attraction with nine consecutive days to use your tickets.  And, with convenient mobile tickets and prepaid admission, you’ll get to skip select lines.  Rest assured that should your plans change, you’re covered by flexible 365-day risk-free returns.