My mother Dorothy Bowers (then Dorothy Novotny) is the woman in the photo. The gentleman is Harry Daniel, who passed away many years ago. She (Dorothy) really doesn't remember the year this was taken, but she arrived in Chicago in 1938 and didn't know Harry until some time in 1939.
The photo was definitely taken at a photo booth at the Chicago Stadium races. My best guess would be that the photo was taken in either 1939 or 1940. -- (submitted by Tom Bowers in 2009)