This chapter traces the historically shifting gay spaces in Chicago, and briefly identifies some of the elements of planning and governance that may have been at work in each period. It reviews the ways in which dynamic conceptions may improve the effectiveness of planning in addressing the issues of lesbian, gay, bisexual, transgender and queer (LGBTQ) people. Anecdotally, housing prices became quite high in Boystown and LGBTQ people who were priced out moved north into Andersonville. Gay bars and clubs may have followed LGBTQ residents to Andersonville, or residents may have followed gay bars and clubs. Soon after the North Halsted Street project was installed, it was clear that gay bars were becoming more numerous in the Andersonville area of Edgewater, particularly along Clark Street. Unlike Boystown, the Andersonville community does not have public or nonprofit infrastructure that marks it as gay.