1. Chicago: City on the Make
    Nelson Algren. It's a prose poem and also a love letter to the city. I read this whenever I'm feeling heartsick for Chicago.
  2. The Man with the Golden Arm
    Nelson Algren. North side of Chicago post WWII. Sexy and seedy. And Frank Sinatra is so good if you want to skip to the movie version.
  3. The House on Mango Street
    Sandra Cisneros. A novel written in childlike vignettes and so powerful.
  4. Coast of Chicago
    Stuart Dybek. A collection of short stories mostly about neighborhoods that are made up Eastern European immigrants.
  5. Native Son
    Richard Wright. Duh. An all time perfect depression era novel.
  6. The Jungle
    Upton Sinclair. Stockyard city.
  7. Sister Carrie
    Theodore Dreiser. Gonna be real honest here; I only got halfway through but I'm gonna try again.
  8. Working
    Studs Terkel. Source material for one of my favorite musicals. A collection of interviews with the working class mostly out of Chicago.
  9. Devil in the White City
    Erik Larson. Due for a reread before we see Leo in the movie.