This chapter follows microcosmic worlds figured in the skyscraper across three “Chicago Schools”: in architecture, in urban sociology, and in political economy. Three novels map three historical phases: Frank Norris’s The Pit (1902), the financialization of wheat in Chicago’s early skyscrapers; Richard Wright’s Native Son (1940), the “color line” and the public sphere on Chicago’s South Side; and Abdelrahman Munif’s Cities of Salt (1984), the landscapes of oil and steel in Dubai. In each the skyscraper appears fleetingly on the horizon, glimpsed out of the corner of the eye as it shifts scales from stage to prop. The three corresponding “Chicago Schools” are: the architects of early skyscrapers assembled around the slogan “form follows function”; the group of urban sociologists that included St. Clair Drake and Horace Cayton, authors of Black Metropolis (1945); and the economists who supplied the neoliberal precepts by which oil wealth was converted into speculative real estate in Dubai and elsewhere. The article concludes with a coda that records, with reference to the work of urban sociologist Janet Abu-Lughod and the writer Deepak Unnikrishnan, the stark divisions of labor that haunt these three “Chicagos” and their skyscrapers, from Lake Michigan to the Persian Gulf.