Things to Do in Chicago

The skyscraper was born here. Chicago sits on Lake Michigan's southwestern shore with the confidence of a city that invented vertical architecture, and you can feel that authority in every neighborhood. The lake creates an almost oceanic atmosphere. What strikes you about Chicago is how it balances Midwestern charm with complete cosmopolitan energy—the food scene runs deeper than deep-dish pizza, though that is worth having, and each neighborhood carries its own personality. Total workaholic energy. You might catch a Cubs game in the afternoon and excellent theater at night, all while the elevated train rattles overhead.

Chicago takes food seriously. From famous deep-dish pizza and Italian beef to a thriving fine dining scene that rivals any major city, the neighborhoods each carry their own food personality. Little Italy for obvious reasons, Chinatown for dim sum and hot pot, Pilsen for authentic Mexican. Restaurant week deals are genuinely good value. The food truck scene has exploded in recent years, and local breweries have multiplied dramatically—they often serve excellent food alongside craft beers.

Summer is when Chicago shines. June through August brings festivals filling the parks, the lakefront becomes the city's playground, and outdoor dining takes over sidewalks everywhere. That said, everyone else visits too, so expect crowds and higher prices. Spring and fall offer pleasant weather with fewer tourists, though Chicago weather can be unpredictable—winter is genuinely cold but also genuinely beautiful, especially around the holidays when the city decorates extensively. Hotel prices drop significantly. You'll have attractions largely to yourself.