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



Check off the culture musts

Green Mill in Uptown

Experience Chicago’s music & nightlife

The Field Museum Maximo
Field Museum

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


Be wowed by city sights

The Ledge at Skydeck Chicago
The Ledge at Skydeck Chicago


  • 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


Garfield Park Conservatory
Garfield Park Conservatory (C) Adam Alexander


  • 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

The Chicago Riverwalk

Urban adventures

City in a garden