This Crosswalk examines how Illinois Medicaid services align with the supportive housing services needed to help people experiencing homelessness, housing instability, and complex health needs achieve long-term housing stability. The report analyzes existing Medicaid authorities, highlights promising opportunities within Illinois’ new 1115 waiver Housing Supports benefit, identifies remaining service and funding gaps, and offers recommendations to better coordinate housing, healthcare, and supportive services. Designed for housing providers, healthcare partners, policymakers, and advocates, the Crosswalk outlines practical strategies to expand supportive housing capacity and improve outcomes for Illinois residents with the greatest needs.