re: Chicago, things to do?

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It seems like most went during the warmer months, I will definitely dive into more of the colder months because it will likely be cold AF and wont be able to do some of the other things you can see/do during summer.

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Plenty of great restaurants, cocktail bars and breweries to choose from. Know for a fact that I've put a good list in one of those threads.

If the weather is 25+ degrees, and wind is bearable, you shouldn't have much issue walking Magnificent Mile and checking out some shops. Otherwise, I always recommend that people walk the boutiques on Armitage (Lincoln Park) and Milwaukee (Wicker Park).

Buying CityPASS will give you access to the Willis Tower, Shedd Aquarium, Adler Planetarium, Field Museum, and Museum of Science and Industry.