Background: High school choice policies attempt to improve the educational outcomes of poor and minority students by allowing access to high schools beyond neighborhood boundaries. These policies assume that given a choice, families will be able to select a school that supports their child's learning and promotes educational attainment. However, research on the effects of public school choice programs on the academic achievement of disadvantaged students is mixed, suggesting that families do not necessarily respond to these programs in ways that policymakers intend. Purpose: The purpose of this article is to identify how family and neighborhood contexts interact with public school choice policies to shape the educational opportunities of inner-city students. Specifically, we ask: What criteria are used to choose schools? What are the implications of these school choice decisions for students' future educational and occupational opportunities? Research Design: We use data from interviews and fieldwork conducted with 118 low-income African American youth ages 15-24 who attended Baltimore City Public Schools at some point during their high school career. Research on school choice tends to rely on data from parents, and we offer a unique contribution by asking youth themselves about their experiences with school choice. Conclusions: Although school choice policies assume that parents will guide youths' decision about where they go to high school, the majority of youth in our sample were the primary decision makers in the high school choice process. Additionally, these youth made these choices under considerable constraints imposed by the district policy and by their family, peers, and academic background. As a result, the youth often selected a school within a very limited choice set and chose schools that did not necessarily maximize their educational opportunity. Our results demonstrate that school choice policies must take into account the social context in which educational decisions are made in order to maximize chances for students' individual academic achievement and to decrease inequality by race and social class.