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.