The purpose of this study is to explore instructional strategies and participation concerns regarding vocal jazz ensembles according to high school choral directors in Illinois who lead their schools’ vocal jazz programs. High school choir directors without jazz experience often recognize the need to expand their performance and pedagogical abilities in jazz and access to vocal jazz repertory; however, professional development opportunities in Illinois’ music education organization have yet to offer guidance. This leaves choral directors without jazz experience little insight on how to familiarize themselves with jazz styles, pertinent pedagogical ideas, and how to apply available resources towards the formation of vocal jazz ensembles. Literature that generally compares and contrasts choral and vocal jazz ensemble instruction exists; however, research has yet to extrapolate concepts applicable to disparate teaching contexts of high school choral programs in Illinois. This study surveys the perspectives of seventy-one choral and vocal jazz directors in various high school teaching contexts in Illinois to provide high school choral directors without vocal jazz programs insight regarding how to approach vocal jazz instruction in their choral programs, regardless of their jazz backgrounds, districts’ socio-economic context, and schools’ musical traditions. Since diversification of musical experience remains a growing initiative in music education, this study’s findings regarding pedagogy and resource application will provide directors with insight on how to expand their curricular explorations within and beyond typical choral programming. Directors would benefit from this insight, regardless of their extant musical-stylistic backgrounds and teaching contexts.