Wells St. was Chicago's oldest and longest-running red-light district. Prostitution was likely present in Chicago even before the city's incorporation in 1833, as suggested by the fact that the Board of Trustees imposed a $25 fine on known brothel owners in 1835. In 1838, record was made of complaints that several houses of ill-repute were operating openly on S. Wells St., between Jackson and Congress (originally known as First St.). The location pictured above is at Van Buren and Wells, halfway between Jackson and Congress.
The area became so infamous that, between 1870 and 1900, the street was renamed First Avenue out of respect to the memory and family of Billy Wells, a noted Indian fighter of the War of 1812, after whom the street had been named. Later, the western tracks of the downtown Loop were located above Wells, no doubt in part due to the lack of organized civic opposition leadership among Wells' entrepreneurs.
The street continued to be a skid row up until the 1980s, and a few hints of its former seediness remain here and there, mostly ignored by the businessmen on their lunch breaks and upscale condo-dwellers who populate the area today.
The location pictured below is Wells St., between Adams and Quincy, once the home to a group of Black-owned brothels collectively known as Shinbone Alley. Today, it holds a parking garage for the Sears Tower, located one block west.