Although one would never guess it today, the one-half square mile or so of Chicago’s "skid row" included Madison Street (from about Clark west), into the early '80s according to one source. That it was into the '60s is for certain, as yours truly used to venture into the neighborhood on occasion then for a haircut at Moler’s Barber School on the south side of Madison. Moler’s was one of the few establishments that didn’t sell cheap wine, beer and whiskey. There were several "hotels" as well that were clearly in the flophouse category. The district dated back into at least the mid/late 1800s, as evidenced by this excerpt from the online Encyclopedia of Chicago:

"The oldest surviving and most visible Chicago rescue mission, the Pacific Garden Mission was founded in 1877 by George and Sarah Clarke in order to keep crooked men straight. Located in the South Loop in the middle of Whiskey Row, the mission took its name from a former tenant, the notorious Pacific Beer Garden."

I’m not sure how crooked men were kept straight, but that’s a conundrum for another time.