In 2013, Chicago Public Schools (CPS) closed 50 schools, leaving 44 school buildings to be sold and repurposed for new uses across the city. This study investigates the process of repurposing school buildings in Chicago and the extent to which these 44 buildings are still serving their respective communities. Eighteen interviews were conducted with academics, journalists, CPS personnel, community members affected by closed schools, and buyers of school buildings. The findings of this study show that chief among the factors that influence the success of repurposing these school buildings are: (1) differences in the vested interests of stakeholders in the closings and repurposing process, (2) inadequate communication regarding the process of closing and repurposing, and (3) obstacles to successful sales and repurposing. This study concludes that the influence of these factors has prevented the majority of the 44 school buildings closed in 2013 from being successfully repurposed.