Hello, jarbabyj:
On the non-fiction side of the shelf . . . .
Capone: The Life and World of Al Capone by John Kobler
Mr. Kobler spends quite a bit of time discussing Chicago, Prohibition, crime, and politics while chronicling the rise and fall of Al Capone. He knows his stuff, and he seems to love Chicago as well. Some readers find his writing mannered and perhaps just a bit twee: at times, he seems the kind of writer who scours Rodale’s and decides that the only fit synonym for “hooker” is “Paphian.” If that makes you smile, Mr. Kobler knows how to show you a good time.
Boss: Richard J. Daley of Chicago by Mike Royko
Mr. Royko has a good journalist’s flair for writing; the narrative never flags and the anecdotes never stop pouring off the page. When he decides to slow down and examine the sociological ramifications of Mayor Daley’s politics and personality, he can be very incisive and perceptive. Unfortunately, he doesn’t always stop long enough to write the few paragraphs that might lend meaning to deeds. Nevertheless, this book is a good introduction to Richard Daley.
Both authors have written extensively about Chicago, and pretty entertainingly at that. Mr. Kobler seems to specialize in the Prohibition era, and Mr. Royko seems to love his city. Both of the books mentioned above contain signposts to other, fine books.
From the fiction side – yes, it’s true you didn’t ask for fiction, but . . . .
Studs Lonigan by James T. Farrell
A trilogy sometimes called The Studs Lonigan Trilogy that comprises Young Lonigan, The Young Manhood of Studs Lonigan and Judgement Day, this is a long unblinking look at Chicago Irish Catholic life from World War I into the Great Depression. Mr. Farrell peppers his character’s dialogue and his narrative with slang and references to fashion: as they live out their lives, Chicago and world events occur around them. His writing can be very clunky but it’s nearly always real and true.
There’s a lot of fiction set in and around the city, The Jungle, by Upton Sinclair, Native Son, by Richard Wright, and The Danny O’Neil Pentalogy, by Mr. Farrell being just three works that jump to mind. Sometimes, naturalistic fiction can lead readers to non-fiction.
Hmm, upon reviewing your opening post and my reply, I realize that I’ve wandered far away from the scope of your requests. Perhaps only the recommendation for Mr. Kobler’s book is relevant, and perhaps my enthusiasms diverted me after I mentioned it. If you found any of the foregoing annoyingly off-topic, I apologize.
Anyway, and at any rate, I hope some of these suggestions send you to the library. If they don’t, I hope someone more attuned or knowledgeable will stop by long enough to jot down a few recommendations.