Shot in Chicago: Movies that capture the spirit of the city

Tim here, rejoicing over the fact that our good host Nathaniel is in my very own Chicago this weekend – we have a movie night planned tomorrow! – and to celebrate, I wanted to showcase some of my city’s best and most dubious moments in the cinematic spotlight. Therefore:
Three Chicago-based movies that truly "get" the city
(no documentaries; that would be cheating, no matter how much Hoop Dreams and The Interrupters are 100% essential Chicago movies)
Mickey One (1965)
The film that Warren Beatty and director Arthur Penn made right before Bonnie and Clyde is even more besotted with the French New Wave, but stylistic excess doesn’t get in the way of a really special hyper-naturalistic depiction of the city streets as they existed almost half a century ago. I cannot, of course, speak to the veracity of what’s onscreen, but the film’s documentary aspects shine through even under the sordid thriller aspects of the plot and Penn’s fractured filming style. Of all the classic movies filmed in Chicago – and there are a few – none do such a great job of suggesting what the neighborhoods looked like way back when, before building and gentrification made their mark.