This article draws on unpublished archival material to illuminate Gertrude Stein’s visits to Chicago during the 1930s. Stein caused a sensation all over the city--especially among the city’s literary ladies--but also met with resistance at the University of Chicago. Stein’s time in Chicago reveals the complex relationship among gender, literary celebrity, and the reception of literary modernism, as well as the ways in which an avant-garde lesbian writer becomes a “great” writer in a tradition that is dominated by men. Most importantly, Stein’s reception in Chicago is central to understanding new arguments not only about Stein’s identity but also about Stein’s aesthetic, which was significantly impacted by her experiences in a city characterized by its “middle”-ness and mobility.