The focus of this study is on understanding different indicators of academic performance in high school, college enrollment, and college persistence of English Learners--including variation in attainment among active and former English Learners--to support their path to high school graduation and access to college. To understand the academic performance in high school, college enrollment, and college persistence of English Learners, this study highlights these metrics for former English Learners and different groups of active English Learners (at the time of enrollment in ninth grade). Active English Learners are divided into long-term English Learners (English Learners who have been classified as such for six or more years) with and without individualized education plans (IEPs) and late-arriving English Learners (English Learners who have been classified as such for fewer than six years). Using three cohorts of recent high school students in CPS, this study found that active English Learners in high school were a very diverse group of students with different outcomes. Those classified as long-term English Learners had more difficulty in high school, were less likely to enroll in college, and were less likely to persist if they did enroll in college. All English Learners, including former English Learners who performed well in high school, were more likely to enroll in two-year colleges compared to the district average. These results imply that active English Learners need different supports as they face different challenges in high school, and that all English Learners face barriers to accessing four-year colleges, compared to native English language students.