Out-of-school opportunities -- such as arts and music programs, sports teams, community service and youth entrepreneurship opportunities -- are increasingly seen as potentially powerful tools to promote positive youth development and to prevent problematic behaviors. Based on in-depth, semi-structured interviews conducted with 99 students in 10th grade in four Chicago Public Schools, this Chapin Hall report explores young people's perspectives on their use of out-of-school time and the influences, barriers, contexts, and processes that contribute to their choices and experiences. The report investigates how young people learn about and choose to get involved in different kinds of out-of-school opportunities and the influence that family members, peers, and non-family adults have on their thinking and decision making. It also explores the relationship between young people's participation in out-of-school programs and their interests, aspirations, and assessments of the kinds of opportunities and barriers found within their families, schools and neighborhoods. Finally, it offers conclusions and recommendations about how to improve opportunities for young people based on the insights provided by them, including specific suggestions about approaches to outreach, access, ongoing engagement and program provision.