This report documents the results of the evaluation of the Families in Transition (FIT) program. FIT was an innovative pilot program based in the city of Chicago that created 100 units of permanent supportive housing (PSH) for families of Chicago Public Schools (CPS) who were experiencing homelessness or doubling up with others. FIT aimed to promote long-term residential stability by coupling permanent housing with case management services using a trauma-informed and strength-based approach. The Inclusive Economy Lab (IEL) at the University of Chicago evaluated the program to measure the effects on students’ academic engagement, as well as their families’ housing stability. IEL’s impact evaluation uses a difference-in-difference design and relies on homelessness data from Chicago’s Homeless Management Information System (HMIS), as well as student academic data from CPS. The study found the program yielded increases in housing stability and provided some suggestive evidence of the program’s potential to reduce school moves. However, the study found no evidence that the program increased school attendance or grade point averages (GPAs). Data from focus groups with participants revealed both the program’s value to families as well as some unanticipated consequences of the program’s structure, including intrusive monitoring of some participating families by their landlords.