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Loews is great. You’ll be in a good spot to check out the lake and parks. What are you into? The art institute is close, as is the museum of contemporary art, and the architecture tours on the river are cool, but so is just walking along there if you don’t want a guide. A lot of the outdoor stuff won’t yet be set up (bars on the beach, bike rentals, etc) but the weather should be good. Food is aplenty. Just hit up yelp and read the reviews. Chicago staples are Italian beef, polish sausage and deep dish. If you want to get out and hang with the hipsters who now believe the 90’s are back, hop the blue line or cab it to wicker park. And if you’re into baseball, a cubs game is always good for the history of wrigley, but the fans are terrible. Sox tends to be less douche-y.