Langston Hughes’s association with Chicago as a nexus for modernism was clearly marked in 1926, when he published four poems in Harriet Monroe’s Poetry: A Magazine of Verse, a leading journal for avant-garde poetry in the English-speaking world. This analysis considers how geocultural contexts in Chicago figured in the development of Hughes’s engagements with modernism. Examining Hughes’s jazz and blues poetry of the 1920s in light of his response to formal innovations by Chicago Renaissance poets such as Carl Sandburg as well as “high” modernists such as T. S. Eliot, I also explore how his critical engagement with Ezra Pound’s imagist poetics was shaped by the prior examples of Sandburg and Jean Toomer, and conclude with a discussion of how Hughes’s literary collaboration with Chicago luminaries such as Richard Wright and his mentorship of Gwendolyn Brooks played an important role in the creative flowering of the Black Chicago Renaissance.