Before the Kennedy Expressway: What Madison Street looked like in 1906

This week’s History Mystery revealed: The photo captures the 700-800 blocks of West Madison Street near Halsted Street, which is now part of the West Loop neighborhood.

  • The buildings in this photo are long gone, mostly demolished to make way for the Kennedy Expressway by 1960.

Yes, but: Let’s look at the clues. The business signs in this photo advertise selling furniture, shoes, pianos and medical services. But that doesn’t give us enough information to identify the street.

Zoom in: Several readers pointed to the sign for the Haymarket Theater as the giveaway, which served as a premier vaudeville theater space at the time. Its location was 726 N. Halsted St.

  • With that information, we can ascertain that this photo was taken a block or two west of the theater, in front of the former Mid-City Trust & Savings Bank Building, which was not built until 1912.
  • The Haymarket…

Story continues

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