This annual report looks closely at how Chicago Public Schools (CPS) students are progressing on the path to and through high school and college. In particular, the report examines three key milestones--high school graduation, college enrollment, and college completion--and tracks how rates on these milestones have changed across time. These rates are then used to calculate an updated Post-secondary Attainment Index (PAI) which represents the proportion of current CPS ninth-graders who 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 over the next decade. The 2021 PAI is calculated using the most recent available data: 2021 high school graduation rates, college enrollment rates for 2021 high school graduates, and rates of college completion for 2014 high school graduates.