This article builds a case for nuanced conceptualizations of "urban" and "-suburban" educational contexts and issues. The author analyzes data across two studies--one of upper-middle-class White parents with children in Chicago public schools, and the other of Black low-income and working-class parents who moved from Chicago to a Wisconsin suburb. The findings suggest that monolithic framings of urban and suburban educational issues and populations can mask patterns of inequality within and across particular locales.