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House on the right is 17342 S Delia Ave, Plainfield, IL 60586. Back in the day, these houses and the grain elevator were part of a hamlet known as Caton Farm, along the Elgin, Joliet & Eastern railroad.
The grain elevator in the foreground goes back to the early 1900s, when Charles Barr operated the company as Barr Grain Co. In a 1909 edition of the Grain Dealers Journal, Mr. Barr submitted a brief update of his business, which as of March 1, 1909 included not only grain merchandising (handled by Mr. C.C. Whipple whose title was Secretary and Treasurer), but also coal, lumber, feed and building materials (handled by Vice President George Hill). The boxy style of the grain elevator was unique for this era, as most were built rather tall and skinny.
In 1911 the Caton Farm elevator was bought by Plainfield Grain Company, a local farmers cooperative organized in the same year. The March 27, 1915 edition of The Farmers Review reported that the local farmers grew tired of Chicago businessmen running local elevators and took action to acquire several Plainfield-area grain merchandisers.
The elevator above didn't last much longer after this photo. Aerial images from 1973 show no evidence of the structures.