[@Poohead189] - One of the best books about Chicago that I've read is [i]Devil in the White City[/i], by Erik Larson. It chronicles the 1893 World's Columbian Exhibition, an event that still informs quite a lot about Chicago [i]to this day[/i], and the monstrous man who made the World's Fair his hunting ground as America's first widely-known serial killer. While the story concerns itself with things that happened over a century ago, you still get an amazing view of how Chicago operates that is directly applicable to today.

I should point out that [i]Devil in the White City[/i] is pure nonfiction; everything in there actually happened and the book is a chronicle of real events and real people. That the story rather reads like urban supernatural horror is part of what makes it so terrifying.