About 1887, W.C. Bishop of Chicago, Ill., and lumberman George N. Fletcher established the Oto, later Bar To, ranch on Fletcher's extensive Dawson County landholdings. A post office opened at the ranch headquarters on May 15, 1889, and was named Chicago in honor of Bishop's hometown and as a humorous reference to the area's sparse population. It served other large ranches nearby, including C. C. Slaughter's Long S. In the 1890s, Fletcher left the venture and A. F. Crowley and W. H. Godair became Bishop's partners, while a village began growing around the post office. B. A. Oden was Oto ranch foreman and postmaster of Chicago from 1894 to 1903. In 1904, Walter Stemmons succeeded him in both roles, the settlement was renamed Stemmons, and a post office was established the same year in the new town of Lamesa, two miles south. Dawson County was organized in 1905, and when Lamesa won the county seat contest, Chicago's residents quickly moved their homes, businesses, school, and Baptist and Methodist churches there, and the community disappeared within days.