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Chicago Surface Lines (CSL) / Chicago Transit Authority (CTA)
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PCC 4401. This was captioned as "4401 at 63rd and Wentworth looking south, at the "Y" located there. The Pennsylvania RR viaduct is in the background. The building immediately to right of the streetcar, a bar and grill at the time, at southeast corner of 63rd and Wentworth behind the tree, still exists."
This photo was one of a number in that area. This is 4401 southbound on Wentworth at 64th in 1957. Exactly the same photo at 7224.
Caption from Gerald Schloetter
Bob Leffingwell photo