While the national debates over the accreditation of Catholic schools remain an essential element of understanding Catholic education during the early 20th century, this study examines how individuals, groups, and institutions grappled with the perceived need for standardization and increased articulation of schools. In particular, it examines the complex reasons for seeking accreditation and the varied responses to these issues by Chicago Catholics. The schools examined for this study were considered nonparochial, four-year high schools (commonly called central high schools at the time) rather than parochial high schools, which were parish-based elementary schools with high school programs. As these schools and their students were almost exclusively Catholic, they allow for an analysis of the experience of a particular religious minority in the early 20th century. The experiences of Catholic high schools in Chicago demonstrated how generating social capital through accreditation came at a price; it required compromise by Catholic schools at all levels. It meant relinquishing complete curricular and administrative independence; however, Catholic educators saw this not only as a worthy and practical compromise, but a necessary one. Through their efforts, Chicago Catholic educators of this era developed schools that thrived and made the opportunity of higher education a real possibility for generations of immigrants and their children. They demonstrated how negotiating assimilation in early 20th century America required both compromise and steadfastness. (Contains 2 tables and 132 footnotes.)