The purpose of this mixed methods study was to learn about the ways that instrumental music teachers in Chicago navigated the urban landscape. The design of the study most closely resembles Creswell and Plano Clark's (2007) two-part Triangulation Convergence Mixed Methods Design, with the addition of an initial exploratory focus group component. Research questions focused on the contextual knowledge that the teachers held regarding their students and communities, the specialized skills they relied upon to be successful, the attitudes and beliefs they held toward teaching instrumental music in an urban school, and the challenges and rewards that they perceived from teaching in this context. The results suggest that the instrumental music teachers utilized their knowledge of the urban context to modify their general pedagogical approach, that they believed a specialized set of skills was required for success in the urban context, that they had relatively positive levels of job satisfaction and believed strongly in the development of their students' potential, and that they faced serious challenges to the success of their programs but also perceived great reward from the personal and musical improvement of their students. (Contains 5 notes, 1 table, and 2 figures.)