The little magazines Poetry: A Magazine of Verse and the Little Review were instrumental in promoting the Chicago Literary Renaissance and Chicago modernism. I investigate their central roles, reading these magazines as privileged sites of modern cultural production and reception as well as important cultural objects in their own right. First, I explain how these magazines relied on local benefactors and advertising to jostle for position among Chicago’s musical, visual, and theatrical arts, as well as within a periodical field that included such other established Chicago magazines as The Dial. I then consider the literary presence of Chicago in both magazines, incorporating digital humanities methodologies to locate Chicago-based contributors (including Carl Sandburg and Sherwood Anderson, along with lesser-known figures) and to identify the many poems and prose pieces associated with the city – highlighting individual literary achievements as well as shared images and tropes.