Jackson Park has been an integral public space in Chicago’s South Side for over a century. As the site of the 1893 Columbian Exposition, the park began its existence as the place where Chicago introduced itself to the world. Since then, several major changes have disrupted Jackson Park and its public use. The U.S. Army used parkland to store missiles, the City of Chicago attempted to reroute Lake Shore Drive through the Park, and private entity Project 120 has proposed developments of a large-scale music venue. This paper examines the ventures that not only threatened to physically change the park, but also compromised local communities of park users and the way they interact with Jackson Park. Most recently, Jackson Park faces major upheaval due to the forthcoming Obama Presidential Center and golf course renovation. Since Jackson Park has been similarly threatened in the past, I examine both the effect and the response towards park changes in order to inform the best ways for the concerned community members to proceed in relation to upcoming projects. Most notably, these past examples tell us that the community of Jackson Park users is often put behind other concerns such as city finances and politics, which indicates that community action is the best, and often only, way for locals to attempt to keep Jackson Park a usable public space.