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Chicago Travel Guide

Photo: Jonny Valiant

Photo: Jonny Valiant

Photo: Jonny Valiant

Photo: Marcus Nilsson

Photo: David Nicolas

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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

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