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 must-haves bites. 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 up and drink in the city

Maple & Ash
Maple & Ash steakhouse in the Gold Coast



Check off the culture musts

Green Mill

Best Large City in the U.S.

Experience Chicago’s music & nightlife

Explore our must-see museums


Be wowed by city sights

Garfield Park Conservatory
Garfield Park Conservatory (C) Adam Alexander


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 all year round
  • Hover above the city and lake on a helicopter tour


  • 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 from the water on an architecture boat cruise (TripAdvisor users ranked the Chicago Architecture Foundation Center River Cruise as Chicago’s #1 tour!)
  • Visit Chinatown in a water taxi — and indulge in more than a little dim sum

Soak in the great outdoors

The Chicago Riverwalk

Urban adventures

City in a garden

Tip: Get the Chicago CityPASS and save 50% on premium admission to Chicago’s top attractions with CityPASS tickets. Includes prepaid admission to 5 must-see attractions:

Valid for 9 consecutive days, Chicago CityPASS tickets cost $108 for adults (value $214) and $89 for children ages 3-11. Buy online at or at any CityPASS attraction. Spend less, experience more.