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Chicago is a city that’s in no need of a publicist. Chat with any person who has lived there, studied there, or just passed through as a tourist, and they’ll rave about the city’s beauty—you know about the beach, right?—as well as its world-class restaurants and awe-inspiring museums. With loads of green space and free events, fascinating cultural pockets, rich architecture, and so very many historical landmarks, the Windy City also provides activities and hangouts for every kind of visitor throughout the year.
For ease of planning, we’ve gathered 41 of the most popular, most fun, most fascinating, and most delicious pursuits Chicago has to offer. Yes, there’s even stuff to keep you entertained during the city’s notoriously brutal winters: Simply head underground (we’ll explain shortly) or to one of the several glass-covered spaces on the list that follows.
When this list is exhausted, which would take more than a few visits and plenty of stomach space, consider just choosing one of Chicago’s many diverse neighborhoods and strolling through for a day, especially if you get there via the much-lauded public transportation system. The metropolis is so neighborhood-focused (and so vast in general) that you could never run out of entertainment, new restaurants to try, and shops to poke through. And when all else fails, just ask for the input of one of those vociferous locals. They’re always thrilled to shout out the best parts of their city—just don’t ask for their opinions on the ever-controversial deep-dish pizza, okay?
