In twenty-first-century Chicago, immigrant musical traditions are reproduced through a number of means. This ethnographic dissertation examines three nonprofit organizations engaged in this work, analyzing their operations and their effects on young people. In doing so, the project argues that such organizations—a relatively novel institutional structure—enable immigrant musicians and community leaders to pursue a wide range of musical and youth development goals that would otherwise be difficult to achieve. Through this study, the dissertation sheds light on broader societal phenomena including ethnic and panethnic formation, musical skill development in non-dominant genres, and youth political organizing. The core of this project is ethnographic study and interviewing with students, parents, teachers, and administrators at Sones de México Ensemble’s Mexican Music School, the Chicago Mariachi Project, and HANA Center—three Chicago institutions that provide musically and pedagogically diverse educations to young people. On both an individual and an organizational level, this project is about navigating the ambiguous middle ground between two dominant frameworks. One of my interlocutors compared life as an immigrant to “a balancing act of two cultures” between the dominant US culture and the culture of one’s parents. The nonprofit music education programs analyzed in this dissertation similarly operate in a third space between the traditional locations of musical learning—formal institutions like schools on one hand, and community spaces like homes and churches on the other. The dissertation explains the productive creativity that happens in this middle ground, as musicians and teachers build innovative educational programs, and both young people and their parents make choices about the kinds of musical lives they want to live.