Perhaps best known for inscribing prairie landscapes and Nebraska small town life in her stories, American author Willa Cather also inserted Chicago cityscapes into her fiction, most notably in The Song of the Lark (1915) and Lucy Gayheart (1935). Having never lived in Chicago, Cather experienced the city primarily as a hub of railway transportation. Multiple encounters over several decades, beginning with a transit of the city when Cather was nine years old, familiarized the author with Chicago’s architectural and cultural features. Commerce and entertainment delivered by rail to Red Cloud, the small Nebraska town in which she spent her adolescence, and to Lincoln, where Cather attended the University of Nebraska, further connected the author with the metropolis. In her short fiction and novels, Cather demonstrates the vital importance of Chicago to the artistic development of her protagonists.