The chapter studies the circumstances under which, Boystown, Chicago’s iconic LGBT community/village, emerged in the 1960s, as well as the changing urban forms and structures that have defined it. It situates the Boystown phenomenon within broader urban development events in Chicago in the post WWII era, and explores linkages between local change and urban and financial regulatory frames at the city, regional, state, and national scales. The study focuses on the geographic core of Boystown, which is identified as the North Halsted Street-Broadway Corridor. It traces urban morphological change in the Corridor (its town plan of lots, blocks, streets, and open spaces, built forms, and building- and land-uses), as a means of illuminating the causes, agents, and structural forces that have produced Boystown.