In this dissertation, I wrestle with how literature has helped frame how modern cities have been understood, and how neighborhood change within them has been interpreted, since the dawn of the modern city in the early twentieth century U.S. Moving from Chicago at the time of the 1893 World’s Columbian Exposition to 1920s Harlem, to postwar Chicago, then back again to 1960s-era Harlem before focusing on the first “brownstoning” era in Brooklyn, I analyze how literature has shaped and contested the terms through which urban neighborhood change was and still is understood—terms like “community,” “integration,” “segregation,” and, on a more housing-specific note, “tenements” and “slums.” Its aim is to demonstrate the necessity of applying close reading to cities in order to understand and address urban problems appropriately in light of their context(s). It also seeks to illustrate how literature can be and has been used as a tool for imagining more equal and more just forms of cities, forms occasionally reached for but never fully attained.