What contributes to the homeless crisis in the United States? Why are some people chronically homeless? How does mental illness impact homelessness? The purpose of this paper is to summarize and critically analyze existing literature and policies regarding the topic of homelessness while specifically focusing on one of the most vulnerable subgroups of the chronically homeless population, the mentally ill. Additionally, San Francisco will be used as a case study in order to determine if the city as a whole fits within the trends explained across the literature reviewed. Policy recommendations are explained in Section 3.