Since I'm living in this big exciting city and plan on going outside as little as possible until this magical, sparkly white stuff goes away - turns out it's really cold! -, I figure I'll make a list of movies that are set in Chicago and make my way through them. Feel free to add to the list if you know of any others!
There are 187 listed here though so I'm fairly sure this list will keep me busy for the remainder of the winter. and next. and the one after.