This qualitative research project highlights the experience of ten Latina/o students in the Chicago Public Schools (CPS). The youth interviewed attended a range of types of high schools; including schools categorized as general education high schools, college preparatory schools, magnet schools and one alternative school. The author conducted life history interviews with ten individuals who identify as Puerto Rican and experienced part or all of their high school years in CPS. The methodology of life history served to provide deeper understanding and analysis of the educational experiences surrounding peers, teachers, counselors and family. This article will provide a brief overview of historical educational practices and policies impacting Puerto Rican children that will help frame the experiences of the youth interviewed. The stories highlighted in this article focus on the youth's experiences while in high school. However, the method of life history provided many rich stories about their lived experiences outside of school which are as important in analyzing their stories of this critical time in the lives of many youth. Their stories were analyzed for a larger study (Davila, 2005) and several themes emerged in that study. In this article the themes of student agency and resistance theory are highlighted. (Contains 2 tables and 7 endnotes.)