The purpose of this annual report on the educational attainment of Chicago Public Schools (CPS) students is to provide practitioners and other stakeholders with an understanding of how CPS students are progressing on the path to and through high school and college. In particular, it examines three key milestones--high school graduation, college enrollment, and college completion--and track how rates on these milestones have changed across time. Where possible, it disaggregates the data by race/ethnicity and gender, disability status, and, for the first time, English Learner (EL) status to understand which students face more barriers to educational attainment and where different strategies and supports are needed. Additionally, to assess the most recent available rates of high school and college attainment in tandem, the report calculates the Post-secondary Attainment Index (PAI), which represents the proportion of current CPS ninth-graders that would complete any degree or certificate from a two-year or four-year college within 10 years, if current rates of attainment were to hold constant during the next decade. [For the 2019 report, see ED615091.]