Youth from families with greater economic means have seen an increase in their participation in extracurricular activities, while the participation levels of youth from working class families have decreased. Knowing the benefits to youth participation in extracurricular activities, communities where youth of marginalized backgrounds reside have an obligation to engage their youth in activities offered through school and community out-of-school time programs. Interviews and focus groups with program coordinators and young adults were conducted to identify how youth in Chicago have been attracted, engaged, recruited, and retained in out-of-school time programs. Program aspects and strategies used to connect with youth and their families emerged, some of which have been previously found in the relevant literature to be positively related to youth outcomes, and some of which are specific to youth who identify as Latine and youth who identify as male. Practical implications and suggestions for future research are further discussed.