The photo is thought to be taken at the Columbian Exposition as part of a 100 mile bicycle trip from the Midway Plaisance in Chicago too Milwaukee. James Oscar Jordan’s two brothers in the photo did not arrived in Chicago until a few days after their ship arrived at Ellis Island on Aug 18, 1893. Thus that is the earliest the photo could be. However, since the three boys have relatively warm clothes, the date is probably no earlier than mid-September. And given the length of the race, my guess is that it was a Saturday in October when it was cooler. Even at 10 mph, the trip would have taken 10 hours and they probably either overnighted in Milwaukee or took the train back. An estimated date is Saturday, Oct 7, 1893, though I could be off a few weeks. The closing of the 1893 World’s Fair took place on Oct 30, 1893.
The original photo at the time was imprinted on a piece of cloth to be used for a pillow cover or wall hanging. In the late 1980s, the cloth was in the possession of Beverly Lynch, daughter of Charles J. Jordan. I asked her about obtaining a photo of it and she had a photographer make a copy. Charles J. Jordan was the brother of my grandfather, Herbert Jordan and both were sons of James Oscar Jordan.
If you would like to add information about this photo, please contact Dave Jordan, a g-grandson of James Oscar Jordan. The Picture Reference Number is DJJ01; Digitized Negatives: 137-23 and 161-10.