The Windy City, the City of the Broad Shoulders, the Second City—there’s a reason Chicago has so many nicknames: this is a city of multitudes. That also means there’s a lot to do here, from fine dining to award-winning local theater to cultural gems like the Art Institute of Chicago. Needless to say, it’s impossible to do everything, but there are some experiences that simply shouldn’t be skipped over. Whether you’re visiting Chicago for the first time or the tenth, here are twenty things you absolutely can’t miss.
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