Chicago
Cities

Chicago

The city that invented the skyscraper, best seen from a boat on its river.

  • Illinois
  • 2 min read

Photo: File:Chicago Skyline in April 2024.jpg: xiquinhosilva derivative work… · CC BY 2.0

Chicago travel guide: the architecture river cruise, Millennium Park and the Bean, Willis Tower Skydeck, the Art Institute, deep-dish pizza and the lakefront.

After the Great Fire of 1871, Chicago rebuilt itself as a laboratory of modern architecture, and in 1885 it built what is often called the first skyscraper. The best way to understand the skyline is the architecture river cruise, which glides past more than a century of towers in 90 minutes.

Downtown, Millennium Park is home to Cloud Gate, the giant mirrored sculpture everyone calls “the Bean”. Next door, the Art Institute of Chicago holds masterpieces such as Grant Wood’s American Gothic and Edward Hopper’s Nighthawks. For a thrill, step out onto the glass ledges of the Willis Tower Skydeck, 412 meters above the street.

Chicago is also a lake city: the 29-kilometer Lakefront Trail links beaches and parks along Lake Michigan. Eat a deep-dish pizza and a Chicago-style hot dog (never with ketchup), and catch a baseball game at historic Wrigley Field.

Don’t miss

  • 1The Chicago architecture river cruise
  • 2Cloud Gate (the Bean) in Millennium Park
  • 3The glass ledge at Willis Tower Skydeck
  • 4Biking the Lakefront Trail

Insider tips

  • Book the architecture cruise for late afternoon to see the towers in warm light.
  • Pay for trains and buses by tapping your contactless card.
  • Head to a neighborhood like Pilsen or Wicker Park for local food and nightlife.

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