Homeless adults may gain access to health services under the Affordable Care Act’s Medicaid expansion, which takes effect in 2014. This study analyzed the health coverage, health status, and health services use of 725 chronically homeless adults with disabilities in eleven cities in the United States. Nearly three-quarters of the chronically homeless adults in this study with incomes below the threshold for the Medicaid expansion were not enrolled in Medicaid. Fifty-three percent were uninsured or relied solely on state or local assistance, and 21 percent had other coverage that included Department of Veterans Affairs health care. The findings on differences in health status and service use across groups suggest that the Medicaid expansion offers important opportunities to increase coverage and access to care for chronically homeless adults. There may be potential savings for states that expand Medicaid, as people transition from state and local assistance to more comprehensive services under Medicaid. Targeted outreach and assistance to enroll eligible homeless people will be necessary. A broad range of physical and mental health services will be required, including case management to coordinate services.