This is one of a handful of historic photos that I was able to correct the history for.
This photo was taken on Wednesday, October 14, 1908 at 1:05 pm as Chicago Cubs fans flock to the streets in celebration of the Cubs Winning the World Series against the Detroit Tigers. Game 5 had a 10 o'clock start time and was played at Bennett Park in Detroit, Michigan.
The image was most likely captured from the photographer standing on the roof of a streetcar.
RESEARCH: The handwritten date on the photographs face, which was misread as 1909, is actually 1908. I inverted the photograph in Photoshop and used other filters to further deduce the last digit was an 8, not the number 9.
Moreover, there is nothing else that would bring such a crowd (flash mob) out into the streets of downtown Chicago bringing traffic to a standstill. News travels fast via telegraph, telephone (by 1905, the total telephones in Chicago proper had increased to 100,000) and word of mouth.