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This research examines the American industrial city in the early twentieth century and the role of cultural institutions in the shift to an urban-oriented society. In-depth analysis of the University of Chicago’s architecture and planning traces how urban form emerged gradually as an assimilation of different traditions. It challenges a planning literature reliant on narrowly-prescribed categories and qualifies recent cultural histories that give a more nuanced portrayal of Progressive Era urban culture but which fail to consider the built environment directly. The research’s critical questions reconsider the role of nature within the city, the definition of the urban public, and the intertwining of commerce and civic culture. Its methodology uses original analytic drawings which trace how the University expanded over time, united with consideration of previously-unexplored written and visual archives. This combination of analytic mapping and archival investigation on one institution reveals new insights into how the industrial city was shaped as a whole. The findings identify paradoxes in the University’s planning, which promoted the dynamism of the modern city while evoking the image of bucolic Oxbridge. These contradictory impulses were enhanced by the University’s location on the Midway Plaisance, a public boulevard typifying the urban/rural hybridity of Chicago’s park system. The result was an urbanised nature, or the charged proximity of urban density and pastoral green space. Disputing the perceived eclipse of the nineteenth-century Parks movement, the term ‘urbanised nature’ suggests how earlier concern for naturalistic landscape was fused with the ideals of twentieth-century Progressivism. The research also contests previous emphasis on the exclusionary cultural practices of this period, as the heterogeneous development of the University’s Collegiate Gothic campus reveals a struggle to balance commercial interests, pastoral imagery, and monumental urban display. More broadly, this research sheds new light on the contradictions that shaped the American city in the early twentieth century—an urban culture driven by the contentious relationship between industrial capitalism and civic institutions, a public realm animated by mass appeal and elite tradition, and a spatial order drawn from urban and rural models.