Chicago’s West Side area developed in the late nineteenth century as the signature location of American urbanism. A steady flow of European immigrants took hold in its various neighborhoods: the Maxwell Street Market brought members of the different ethnic communities together; Hull House became globally known for the work of Jane Addams and the invention of the settlement house. For the urbanist, this is hallowed ground. Following World War II, the West Side was selected as the center of the urban campus of the state university. The campus grew exponentially, and the old neighborhoods were rebuilt, often without remembrance of what had previously stood on this ground. A set of tensions emerged between city and university, and efforts were made to bridge these differences, both present and past. This chapter tells the story of how one university campus in a great world city continues to relate to its surrounding urban environment, seeking to sustain itself while relating to both its present neighbors and those whose turbulent times, while gone, continue to deserve attention and respect.