This report spotlights an effort in Chicago Public Schools to structure student experiences across the largest district in Illinois: to structure student experiences across grades 6–12 that support robust postsecondary preparation inclusive of multiple postsecondary pathways. Chicago Public Schools district leaders and staff have adopted a career-connected learning (CCL) framework to guide the design and implementation of college and career readiness experiences, which this study documents. Using student and school data from the 2017 school year to the 2024 school year and newer data collections, where possible, this report provides a snapshot of the career and technical education, work-based learning, and advising activities central to CCL. In addition, it reports findings from extensive field work with system architects and practitioners that capture the conditions and motivations under which the transition to CCL has taken place.