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For the inaugural gallery in our “Great Cities” series, LIFE.com chose to focus on a place that, in so many ways — from the triumphant to the deeply troubling — remains an emblematic American metropolis. Inspired by these extraordinary pictures, made by LIFE photographers from the 1930s to the 1970s, Chicagoist editor-in-chief Chuck Sudo pays tribute to the town he loves: the Windy City, that toddling town, sweet home Chicago.
Chuck Sudo is editor-in-chief of Chicagoist. Part of the Gothamist network of local-centric sites, Chicagoist is dedicated to reporting on life in the Windy City in all its facets and in 2012 was named one of Chicago’s top online news sites by the Community Media Workshop. Chuck was born and raised on Chicago’s Northwest side and has called the Bridgeport neighborhood on the South Side home for 15 years. Follow Chuck @bportseasoning.