This chapter studies the historical “Chicago fictions” that Theodore Dreiser published between 1900 and 1915, showing how they chart the city’s growth and development between the Fire of 1871 and the turn of the twentieth century. The chapter also outlines some of the literary techniques that Dreiser used in his attempts at capturing the city's dynamism, focusing on his novels’ indeterminate sense of historicity, their generic and stylistic heterogeneity, their emphasis on unsettled and changeable characters, and their simultaneously backward and forward-facing perspectives.