There’s a lot of ways you can do Chicago. If you’re going for the first time, you’ll want to hit up all the classics. We’ve put together this definitive list of the essential Chicago musts, from iconic attractions to award-winning restaurants. To be fair, you won’t be able to complete the bucket list in a single weekend — but it’s a pretty good excuse to plan another trip back.
Eat and drink the best of the city
Eat
- 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 our Michelin-star restaurants and James Beard Award winners
- Savor summer with a colorful scoop — Chicago’s own Original Rainbow Cone
Drink
- Experience the craft beer capital of the country at over 70 local craft breweries
- Get spirited at Chicago’s world-class distilleries, from KOVAL to Chicago Distilling Company
- Try some of the city’s best mixology at these top Chicago cocktail bars
Check off the culture musts
Experience Chicago’s music & nightlife
- 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
- Hang out with music fans — about 100,000 of them — at Lollapalooza
- 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. Don’t worry to 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
Theatre
- 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+ theatres
- See theatre stars and acclaimed shows at Chicago’s Tony Award-winning theatres
- Catch modern takes on the classics at the renowned Chicago Shakespeare Theater
- Discover up-and-coming talent at these cutting-edge neighborhood theatres
- Enjoy experimental and avant-garde theater lakeside at the stunning Theater on the Lake
Be wowed by city sights
Thrills
- 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
Experiences
- 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
Sights
- 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”
Soak in the great outdoors
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
