This annual analysis provides a district-level view of Chicago Public Schools (CPS) students' patterns of educational attainment. It presents a starting place for thinking about why these patterns exist and what can be done to improve these patterns. The report focuses on three key milestones--high school graduation, college enrollment, and college completion--and uses them to calculate a Post-secondary Attainment Index (PAI). Where possible, the authors disaggregate the data by race/ethnicity and gender, disability status, and English Learner (EL) status. The PAI and its components are best understood as a measure of progress over time rather than point-in-time estimates for a particular cohort. The authors therefore recommend focusing more on long-term trends than on year-to-year fluctuations. Fully supporting CPS students throughout their high school and post-secondary journeys will likely require an unprecedented level of investment and new partnerships across the city. An understanding of the lived experiences of CPS students and graduates impacted by the COVID-19 pandemic is also needed to inform investments, partnerships, and changes to practice.