UPDATE: The photos previously displayed in this post were of the wrong side of the street. For accurate photos of the current location of 441 S. Clark St., see this post focusing on Carrie Watson.
441 S. Clark St. was a brothel belonging to Annie Stewart from 1862-1868. Madam Stewart left her house in 1868 after one of the girls shot a local constable who had come to visit the resort and cheated at euchre. The girl was arrested, but exonerated after it came to light that the constable had tried to choke her first. The judge ruled that she "had not forfeited her rights to self-protection by resorting to the disreputable life of a cyprian." Nevertheless, Annie Stewart's career was over, and another madam, Carrie Watson, took over the lease. Madam Watson raised the standards of the house and catered only to men of success, continuing to operate the house into the 1890s, after which it was demolished for use as a train car yard.
Chicago's chaotic house numbering system was changed in 1909, so that this location would today be numbered in the 800 block of S. Clark.
In the 1890s, the arrival of electric trolley cars running down Clark St. caused commuters to put political pressure on the city government to clean up the area, and Carrie Watson retired.