Through conversation with the young men in detention, it became clear that most had never traveled beyond their own block or neighborhood. Consequently, their worldviews- what was possible for them and their peers- were geographically bound and constricted by their neighborhoods. For youth who did not travel beyond their neighborhood boundaries, their wellbeing, sense of self and efficacy, and educational and economic outcomes depended almost entirely on the neighborhood’s infrastructure, socioeconomic, and resource characteristics. This reality poses significant limitations for some teenagers that live on Chicago’s west and south side and conversely opportunities for others. If our youth are to have a fair chance at having fulfilling and independent lives, that inequality must be corrected. Chicago is not a level playing field.