Having recently visited the Windy City, I’m looking a good general overview of the city’s history from roughly the time it was founded to at least the mid-20th Century.
It doesn’t fit the whole history of the city that you’re looking for, but I loved Devil in the White City for the way it weaved in many stories and also well described the feel of Chicago in the late 19th century.
Another vote for Devil in the White City. Awesome book.
*City of the Century *by Donald Miller.
You’re welcome.
“Boss,” by Mike Royko, explains how it became what it is.
ETA: Richie may have even beat his dad, but Dick laid the groundwork.
Same here.
*Devil in the White City *is an amusing look at a slice of Chicago history but it doesn’t remotely fit the OP’s needs.
City of the Century is one of the great books of urban history ever written. There is no competition between the two.
From a somewhat different perspective, a couple I enjoyed were:
The Chicago River, Libby Hill
A Natural History of the Chicago Region, Joel Greenberg
Chicago in maps: 1612 to 2002, Holland, Robert
The first is a little amateurishly produced, and was a tad tedious at times, but I found it fascinating. After all, the rivers, and the sub-continental divide, are pretty much the only reasons Chicago exists where it does.
The second is L-O-N-G, with sections on every aspect of the region’s natural history I could imagine: geology/wildlife/plants/etc. A bit of work to get through, but definitely worthwhile for anyone interested in the area
The third is a lot of fun for anyone who likes maps. Interesting representations of how man interpreted and portrayed the Chicago-area over the years.