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

Build out your Chicago itinerary with this bucket list of things to do, eat and drink. These are the classics. The essentials. And by no means does it cover all that the city has going on. You could pick up and stay here forever, and STILL not get to everything. But this is a great place to start!

Chicago Bucketlist | Food & Drink

Food & Drink: Bring an Appetite!

❏ Eat pizza... lots of pizza. Deep dish and thin crust alike. Just eat a lot of pizza. 

❏ Pile 7 toppings on a hot dog... it's the Chicago way  

❏ Devour a bag from world-famous Garrett Popcorn — sticky fingers and all! 

❏ Go on a multi-day bender between your choice of over 50 local craft breweries 

❏ Master the Italian stance as you tackle an Italian beef sandwich

❏ Eat your way through Chinatown... and Greektown... and Uptown... and Pilsen... and all our foodie neighborhoods 

❏ Tackle the biggest cut you can at a Chicago steakhouse


❏ Embark on an epicurean adventure — can't go wrong with our 22 Michelin star restaurants and 40+ James Beard Award winners

❏ Make friends with the bartender AKA mixology masters on the craft cocktail scene 

❏ Savor summer with colorful scoops from Original Rainbow Cone or Mario's Italian Lemonade, just two of 20 must-eats in Chicago

Chicago Bucketlist - Arts and Culture

Arts & Culture: Music, Museums & More!

❏ Pack a picnic for Millennium Park's free Pritzker Pavilion performances 

❏ Hear blues master Buddy Guy live at Buddy Guy's Legends in January 

❏ Hang out with fellow music fans — say about 300,000 of them — at Lollapalooza

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

❏ Relive the Al Capone era at Green Mill Jazz Club in Uptown 

❏ Hear living legends at Chicago Jazz Festival

❏ Pay homage to the genre that calls the Windy City home: Chicago Blues Festival 

❏ Face off with Sue the T.rex at The Field Museum 

❏ Meander the Art Institute of Chicago... Ferris Bueller-style 

❏ Stand in the tornado at the Museum of Science and Industry

❏ Watch the beluga whales and dolphins at the Shedd 

❏ See why space is freaking awesome at Adler Planetarium 

❏ Hop on the first 'L' car at the Chicago History Museum, or even better, catch a ride on their guided 'L' train tour 

❏ Go on a public art jaunt — from murals to Miró and Picasso

❏ Sit in the "Splash Zone" at Blue Man Group 

❏ 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 theatres

Chicago Bucketlist - Tours and Attractions

Tours & Attractions: The "Bean" and Beyond

❏ Brave the 1,353-foot-high challenge: The Ledge at Skydeck  

❏ Take a #BeanSelfie

❏ Flex your photography skills on an architecture boat cruise 

❏ TILT over the city at 360 Chicago 

❏ Get spit on by a Chicagoan... the larger-than-life "gargoyles" of  Crown Fountain

❏ Find lions, tigers and bears (OH MY!) at Lincoln Park Zoo  

❏ Survey the 5,000 varieties of plants at Garfield Park Conservatory


❏ Look up at Navy Pier... fireworks and a Ferris wheel rule the skies here

❏ Go up yourself... on a helicopter ride

❏ Spend, spend and spend some more on The Magnificent Mile 

❏ Geek out as you tour one of the Frank Lloyd Wright masterpieces

❏ Sing the Married with Children theme song at Buckingham Fountain 

❏ Take a picture with the Chicago marquee at Chicago Theatre 

❏ Zip along in a water taxi down to Chinatown  

Bucket list

Sports & Outdoor Fun

❏ Join the Chicago sports fan frenzy at a Bears, Bulls, White Sox, Cubs, Blackhawks, Sky or Fire home game

❏ Follow the paparazzi to the Harry Caray statue 

❏ Snap a picture with #23... or at least the Michael Jordan statue

❏ Shake hands with Southpaw or Benny the Bull


❏ Work up a sweat (or catch a sunrise) along the Lakefront Trail

❏ Stop and smell the flowers at Lurie Garden 

❏ Skate the ribbon or scale the massive climbing wall at Maggie Daley Park 

❏ Bike, skate, walk, run... get your fitness on along The 606  

❏ Paddle through an architectural canyon on a river kayak

❏ Go zen at an outdoor oasis like Osaka Garden or Promontory Point

❏ Stroll the Chicago Riverwalk 

❏ Catch a tan at one of Chicago's beaches 


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.


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