This chapter reexamines the role urbanization played in the emergence of literary modernism in the US. The development of the skyscraper in the 1880s and increasing, and increasingly diverse, migration patterns at the turn of the twentieth century transformed Chicago and New York into important economic and cultural centers, where new literary voices and new modes of literary expression soon flourished. This chapter explores the significance of the skyscraper, that most American of architectural forms, on modernist poetry and prose fiction, as well as the ways cities enabled authors to create and navigate complex, intersecting networks of literary community. Harriet Monroe and Claude McKay serve as exemplary representatives of the modernist literary cultures that took shape in – and sometimes between – Chicago and New York, respectively.