The Year Diz Came to Town, by Robert Goldsborough

You forgot Stephen Elliott's HAPPY BABY, which details the contemporary seedy underside of Chicago, and--most importantly--the story of homeless/foster children left to fend for themselves in Chicago group homes.

Another book to add to your list, Nella Larsen's PASSING, written by a native who became a figure in the Harlem Renaissance.

I'm not sure how you overlooked Adam Langer's Crossing California (and its follow up, The Washington Story)--they capture West Rogers Park in the late 70s and through the 80s so perfectly. Also, The Time Traveler's Wife by Audrey Niffenegger feels like a quintessential Chicago novel to me too (especially for Chicago book lovers, with its scenes set in libraries and bookstores in the Chicago area.) I am a Chicagoan living in California, and all of these books helped me feel happily re-connected to my hometown.

Time Traveler's Wife. I think it's important to select a text that has sold a few copies.

Tough choice from a good list of great novels, but how can Willard Motley's novel, "Knock on Any Door" be excluded? And also, to a lesser extent, his follow-up novel, "Let No Man Write My Epitaph".

The Easy Hour by Leslie Stella or Crossing California by Adam Langer

The Devil in the White City

Time Traveler's Wife might have sold a few copies, but it's not very good.
Devil in the White City is creative non-fiction.

I like this list. It was full of surprises.

Time Traveler's Wife is a great book. Devil in the White City was entertaining. Some of Harry Stephen Keeler's books have great scenes around the city revealing a daily sense of place from the 1920s you don't get from a history book.

Time Traveller's Wife is fantastic.

A Death in Pilsen is the latest in the Snap Malek Mystery series and worthy of mention.

Note: "The Year Diz Came to Town" has been revised and published as "Three Strikes You're Dead." This is book one in the Snap Malek series. Book two is "Shadow of the Bomb."

I'm prejudiced. I read Theodore Dreiser for fun. I think Sister Carrie is an important novel even with Dreiser's lengthy preaching and moralizing. There are times when the man simply shocks me with his poetic prose. Dreiser's writing style is certainly out of fashion, but I don't think his themes are.

What about John R. Powers' "The Junk Drawer Corner Store Front Porch Blues"? That book really feels like my old neighborhood, West Lawn.

A Mild Form of Madness. The number of true Chicago characters in there was just fantastic. Takes the reader through all the neighborhoods, it's funny and violent and just great.