Ten books that capture the 50s of Chicago

At The Culture Trip Karla Sullivan tagged ten books that capture the 1950s of Chicago, including:
Letting Go

Philip Roth’s first book, Goodbye, Columbus, won the 1960 US National Book Award for Fiction, but his subsequent books are equally important. Set in the 1950s in Chicago, New York and Iowa City, Letting Go concerns the lives of three characters that struggle as they deal with the social