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

People sharing dumplings in Chinatown
Head to Chinatown for some of the city’s best dumplings.

Top Chicago eats

Chicago bars, breweries, and beyond

Check off the culture musts

Green Mill in Uptown

Experience Chicago’s music and nightlife

The Field Museum Maximo
Field Museum

Explore our must-see museums

See Chicago theatre

Be wowed by city sights

The Ledge at Skydeck Chicago
The Ledge at Skydeck Chicago

Top sights and attractions

  • 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.
  • 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).
  • Gaze up at Chicago’s famous Marina City towers (aka the corncobs), featured in everything from movies to album covers.
  • Get up close and personal with art masters — from Caldwell to MirĂł to Picasso — on a public art tour around the city.
  • Step back in time at the historic Pullman National Monument.
  • And, of course, take a selfie with Cloud Gate, aka “The Bean”.
  • Discover under-the-radar attractions and hidden gems in our diverse neighborhoods.

Waterfront adventures

Soak in the great outdoors

Friends bike on Chicago's Lakefront Trail
Chicago’s Lakefront Trail; photo by Abel Arciniega, @tequilagraphics

Urban adventures

City in a garden

Attend iconic events

Music festivals

Chicago sports

  • See the Chicago Cubs play a home game at historic Wrigley Field, the country’s second-oldest ballpark.
  • Root for the Chicago White Sox at Guaranteed Rate Field and stay for post-game fireworks.
  • Feel the electric energy at a Chicago Sky basketball game at Wintrust Arena.
  • Sing “Bear Down, Chicago Bears” during a Chicago Bears football game.
  • Watch the Chicago Blackhawks take the ice at the United Center.
  • Also at the United Center, cheer on the legendary Chicago Bulls basketball team.
  • Enjoy the non-stop energy of a Chicago Fire soccer match at Soldier Field.
People at Christkindlmarket Chicago
Christkindlmarket Chicago

More can’t-miss events

See the best attractions in Chicago at up to 48% savings with CityPASS.

Explore the famous Shedd Aquarium, see scientific discoveries at the Field Museum, take in spectacular views from the Skydeck and more! With two options to choose from and up to 9 days to enjoy, you can't go wrong.

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