Poet Carl Sandburg immortalized Chicago as the “City of the Big Shoulders,” paying tribute to Chicago’s formative brawn. The self-made, industrious town rebuilt after a devastating 1871 fire, nurturing new styles of architecture and distinct flare for innovation. A green apron of lakefront parks buffers the city’s 29 miles (47 kilometers) of Lake Michigan shoreline from which 77 neighborhoods unfurl westward spanning the downtown Loop, the elegant Gold Coast, the bohemian Wicker Park, and deep ethnic pockets such as Chinatown. The combination of grit and grandeur here is somehow purely American. Loving Chicago, said author Nelson Algren, is “like loving a woman with a broken nose, you may well find lovelier lovelies. But never a lovely so real.”
It's no wonder Frank Sinatra paid tribute to Chicago in his ubiquitous song "My Kind of Town." Here's a list of free, year-round art, music, theater, dance, and walks that will keep you singing Sinatra.
Travel to Chicago, the epicenter of activity on Lake Michigan's southwestern shore.
See our gallery of the best hikes within an hour of U.S. cities where the only prerequisite for exploring is a pair of sneakers.
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2014 Traveler Photo Contest
See all the winning images from the 2014 Traveler Photo Contest.