Chicago

Anish Kapoor’s stainless-steel Cloud Gate,
in Millennium Park.

Photo: Jonny Valiant

Photo: Marcus Nilsson

Photo: David Nicolas

Launch Slideshow

Recommended Links

Find Chicago Hotels on Y! Travel
Top Chicago Restaurants, from Travels in Taste

Chicago feeds on extremes, and on its own uncanny knack for reinvention—a trait that likely began with the Great Fire of 1871, which devoured one-third of the city. It’s hard to think of another American city that so gracefully and seamlessly combines extreme urbanism (the rattling El, the astonishing 110-story Sears Tower) with tranquil green space (sandy beaches, the glorious Millennium Park); whose cuisine ranges deftly from cutting-edge (Alinea, Avec) to casual (Windy City dogs, the namesake deep-dish pizza); or whose cultural offerings include not just world-class museums and a superb theater scene (Steppenwolf, the Goodman) but gritty blues joints, comedy landmarks (Second City), and two beloved baseball teams (yes, in Chicago baseball is culture). All this in a prime location on the shores of shimmering Lake Michigan. See the slideshow.

Don't Miss

Watching a Cubs game from the bleachers at Wrigley Field—the second oldest ballpark in the majors
Laughing ‘til your sides hurt at Second City, Chicago’s famous home for comedy improv; or, taking in some serious drama at acclaimed Steppenwolf Theatre
Catching a glimpse of the historic Windy City skyline—the John Hancock Center, the Sears Tower, and the Wrigley Building—on an architecture river cruise along the Chicago River