Large urban school districts are increasingly offering their students options that break the link between residential location and school attendance. Individual decisions are likely to aggregate in different ways across communities, leaving students in some neighborhoods with more varied educational experiences. In this paper, I explore these patterns using a complete cohort of Chicago Public School high school freshmen in 2009 (N = 24,019) and explore the characteristics of different schools that students living in the same neighborhood attend. Students in poor and violent neighborhoods attend schools that are more heterogeneous in terms of type, achievement, safety, and student demographics. Students from these neighborhoods also scatter geographically to schools across the city, many traveling quite long distances. In contrast, students from safe and affluent neighborhoods attend many fewer schools, are less likely to make long distance trips, and are more likely to attend school with a large proportion of their neighbors.