The Citywide Education Progress Reports evaluate how a city is doing across three goals: (1) The education system should be continuously improving; (2) All students should have access to a high-quality education; and (3) The education strategy should be rooted in the community. Across each goal, indicators are presented of system reforms and outcomes. These city reports focus on education strategies for the 2017-18 school year. Analyses reflect developments through June 2018, and these are updates to the original reports from the 2016-17 school year. To understand how well cities are doing, the Center on Reinventing Public Education (CRPE) used state and federal data to track school improvement, graduation rates, and student access to high-quality schools. To understand city strategies and identify early progress, interviews, surveys, public documents, and news articles from 2014-2015 to the present were relied upon. This analysis uses data for district and charter schools to look at all schools within municipal boundaries, rather than just one sector or district. Chicago can be proud of increased student performance: according to research lead by Stanford professor Sean Reardon, Chicago students are learning at faster rate than 96% of school districts in the country. Janice Jackson, a previous Chicago Public Schools (CPS) student, teacher, principal, and administrator, was tapped to serve as CEO in 2018. The system is giving more decision making authority to individual schools, developing strong school leader pipelines, and has introduced a unified information and enrollment system for all public high schools in Chicago. But the city must remain focused on elevating voices of underrepresented communities in the system, planning for quality schools in every neighborhood, and providing better transportation options. [For the main report, "Stepping Up: How Are American Cities Delivering on the Promise of Public School Choice?," see ED578178.]