This chapter analyzes how turn-of-the-twentieth-century Chicago fiction responded to rapid urbanization. Chicago qualified as what Asa Briggs has called a “shock city”: it embodied the disruption of the Industrial Revolution. The city challenged the nineteenth-century pastoralist view of the American republic because it rose in just a few decades from the Midwestern heartland. Chicago’s urban novelty triggered a reconfiguration of American fiction as writers grappled with a social reality resisting nineteenth-century literary codes. Two varieties of Chicago fiction – realist novels of manners (Henry Blake Fuller; Robert Herrick) and urban naturalism (Theodore Dreiser; Frank Norris; Upton Sinclair) – negotiated this cultural change. The former perpetuated the formula of domestic fiction in a context where the kinship-based knowable community was threatened by economic forces undermining its foundation. The latter sought to represent the new economic determinants through discourses relying on nature romanticism and the gothic. The shift from novels of manners to naturalism produced a new literary topography of the urban world, marking the transition from realism to modernism.