I believe in the old fashioned form of preparation:  reading a good book.  For Chicago, there are many books to choose from, but my favorite is Nature's Metropolis:  Chicago and the Great West by Professor William Cronon of the University of Wisconsin at Madison.  (W.W. Norton.  New York, 1991).

 

What makes this book so valuable is that it explains the way that Chicago, as a kind of economic vortex, shaped the whole middle section of the country, ecologically, economically and culturally.  The building of railroads pulled iron from the northern Great Lakes and created inland navigation on an oceanic scale.  The hunger for grain and meat shaped the landscape all the way to the Rocky Mountains.  The methods developed to trade commodities shaped finance.  Cronon's is a truly comprehensive view.

 

I Among other things, this book is the key to understanding the history of my own family.  My wife had an ancestor who died in Michigan from a logging accident known as a "widowmaker."  Even he was part of Chicago history as defined broadly by Cronon because logs were being felled all over the Midwest to meet the building needs of Chicago.  One of my own direct ancestor came here from Norway in 1854 amd became a cooper in the Water Street market, lending his muscle to Chicago's role as the greatest trading center between the coasts.  The fact that my grandfather rose with an eighth-grade education to become executive vice president of the First National Bank of Chicago on the strength of his expertise in loans to the construction industry is a perfectly understandable event, set against the Cronon's background.

 

Looking beyond Cronon's invaluable book, the Chicago History Museum has a fine collection of Chicago histories available to be purchased on-line.  Browsing that site is a very good introduction to respected books about Chicago.