This report, produced in cooperation with Mills College, presents findings on the academic and personal experiences of students and teachers in small high schools created by the Chicago High School Redesign Initiative (CHSRI), a partnership between the Chicago Public Schools (CPS), the Bill and Melinda Gates Foundation, and local foundations. The authors examine CPS administrative records, test score data, and responses from the CCSR 2005 Improving Chicago’s Schools Survey to compare CHSRI schools to other Chicago public high schools. CHSRI schools showed better outcomes than CPS high schools on several measures, but on others there was little notable difference. For example, though CHSRI teachers felt that their schools offered a more supportive context for reform than teachers in other CPS high schools, the CHSRI teachers did not demonstrate instructional practices that were any different than CPS teachers’ instructional practices. CHSRI students were absent fewer days than similar non-CHSRI students and were less likely to drop out of school. Juniors also reported higher expectations from teachers and both juniors and freshmen reported greater personal and academic support than non-CHSRI students. However, juniors at CHSRI schools did not score differently on the Prairie State Achievement Exam than similar students at CPS high schools. This initiative is relatively new and it may take additional time for the beneficial effects of these small schools to become evident. This report points to important concerns about a reform strategy that is gaining momentum in Chicago and other districts, and it lays the groundwork for future investigations of the initiative.