Urban vacant land is a pervasive feature in many U.S. cities. Following the 2008 foreclosure crisis, local governments sought to reduce the high concentration of municipal-owned vacant land through initiatives that transferred lots to private ownership. This approach provided short-lived financial benefits but left large amounts of vacant land without plans for reutilization. This research explores how municipal strategies can adopt a temporary use model that allows for incremental, short-term interventions on vacant land. Focusing on Chicago, this paper compares the city’s former Large Lots Program with three case studies in the Washington Park neighborhood to illustrate different approaches to vacant land reutilization. Using a descriptive evaluative framework, this paper argues that embracing a temporary use model promotes socio-ecological benefits that can mitigate the adverse impacts resulting from high concentrations of vacant land and support community-led transformation.