Over the past several years, Chicago's educators and community leaders have elevated an all-too-delayed dialogue about the systematic barriers facing communities of color. 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, it examines five key milestones: (1) Freshman OnTrack; (2) high school graduation; (3) college enrollment; (4) college persistence; and (5) college completion, and track how rates on these milestones have changed across time. The goal is for readers to come away from the report with a clearer understanding of the current state of educational attainment in CPS and be motivated to take part in conversations and action to dismantle the oppression inherent in the current systems. [For the 2018 Research Snapshot, see ED608111.]