Walking Madison Street


[This piece also appeared in “Checkerboard City,” John’s weekly transportation column which appears in print in Newcity magazine, hitting the streets on Wednesday nights.]

Chicago’s Madison Street, named for the chief author of the U.S. Constitution, runs through the most expensive real estate in town as well as some of the most underserved neighborhoods. As the city’s north-south bifurcating street, it forms the Mason-Dixon Line between the North Side and the South Side. Over the years I’ve hiked the entire lengths of several Chicago thoroughfares in search of fascinating sights and interesting people, so it was only a matter of time until I walked Madison, a relatively short street at eight miles, but dense with landmarks.

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