As the City of Chicago celebrates receiving a $60 million federal grant to provide over 700 units of permanent supportive housing and 50 units of short-term housing, the Center for Housing and Health (CHH) is also celebrating another milestone as it proudly reports that its Flexible Housing Pool (FHP) program has successfully housed more than 1,000 Chicagoans experiencing housing instability. Since the program’s 2019 inception, the City of Chicago, the public sector, hospitals, managed care entities and private philanthropy all committed over $45 million in funding to support the FHP. These combined efforts have resulted in successfully housing 1,002 individuals in 620 different households. Among the housed individuals are over 350 children, most of whom are part of youth-led households. Through bridging housing and health care systems, the FHP improves program participants’ housing stability and health outcomes, increase income, and demonstrate a decrease in the frequent utilization of emergency services and hospitalizations, and interactions with the justice system. Ninety-seven percent of all individuals housed through the FHP maintained stable housing for a least a year.