To improve college and career readiness and success in Chicago, Education First collaborated with Chicago Public Schools (CPS) and City Colleges of Chicago (CCC) to develop a Student Success Roadmap to guide the partnership between the two institutions. We examined CPS and CCC’s efforts to date, including analyzing a variety of student achievement data; worked with key stakeholders to consider the assets and barriers in place; and, ultimately, supported CPS and City Colleges to build—and organize itself to execute—a five-year strategic roadmap to achieve equitable outcomes and success for the city’s most underserved students, in alignment with local four-year institutions.