I lived in Chicago for 20 years and thought I knew the city. No Way. This is a fascinating book. It is not a "history" of Chicago, but rather a collection of the facets of its history that made it into the city it is today.
My only complaint was with geographical details. For example, a chapter on "the Levee" with all its decadence was great -- but nowhere does he identify where "the Levee" was. It is a location that has passed into Chicago lore, so nowhere in today's Chicago would anyone know where it existed.
If you are a Chicagoan or a wanna-be fan, you need to read this book.