Students and parents rely on public schools to be catalysts of social mobility, but too often already disadvantaged students are served by the poorest-performing schools. This paper assesses how the spatial placement of subsidized housing in Chicago—including traditional public housing, privately owned subsidized rental units, and Housing Choice Vouchers—impacts the elementary educational experience of residents. A multivariate spatial analysis of subsidized housing and school quality reveals that some of the city’s poorest-performing schools, as measured by standardized test scores in reading and math, serve some of the highest concentrations of subsidized housing residents. In addition, elementary schools attended by residents of subsidized housing have, on average, lower test scores, higher percentages of Black students, and higher percentages of students receiving free or reduced price lunch than the city average. Residents of traditional public housing fare the worst, while residents of privately owned subsidized housing and Housing Choice Voucher holders attend slightly higher-performing schools. Interviews with four parents of Chicago elementary students, including residents of both subsidized and market-rate housing, suggest that both school quality and a safe neighborhood environment are highly important to parents, but that affordable options near desirable schools are limited. The findings support a reevaluation of Chicago’s housing programs to prioritize access to effective schools with new project-based developments, transfer resources to tenant-based subsidies with greater residential choice, provide relocation counseling to all residents who want it, and increase the supply of affordable housing in high-opportunity neighborhoods.