© Meredith Miotke / Culture Trip

Insider Travel Guide to Chicago

The third-largest city in the United States, Chicago has made countless contributions to American culture, including deep-dish pizza, the Cubs and its own style of jazz. The Windy City began as a trading post beside Lake Michigan, but its rapid-transit system transformed it into a global city that boasts a world-famous skyline and Millennium Park. Each neighborhood in Chicago has a unique history and feel. Head over to the Loop to check out beloved sites like Grant Park and Willis Tower. For the ultimate foodie experience, sample Wicker Park’s trendy restaurants and bars. Or venture off on your own – there’s something for everyone here.

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The Best of Chicago Tourism

Visiting a city as culturally rich as Chicago can be daunting – let our travel guide help you prioritize. The Art Institute of Chicago is a must-visit. Sports fans can catch a game (and a Chicago hot dog) at Wrigley Field, and music enthusiasts will love the jazz at the legendary Green Mill. For a day outdoors, try boating on the Chicago River, the only river in America that runs backwards.

Neighborhoods in Chicago