Many homeless children and youth have difficulty in school due to their loss of stable housing, and lack of consistent contact with family and friends. When a child becomes homeless, schools are federally mandated to identify these students and provide the same access to a free and appropriate education as their non-homeless counterparts. Within a historical and legal context a review of federal and state legislation that addresses the education of homeless children and youth will be conducted. This paper will provide an overview of the history of homelessness in the United States, specifically its impact on homeless children and youth and its relationship to education. It will outline a critical analysis of The Chicago Public School Systems' response to these federal and state laws in an effort to demonstrate the need for continued support, advocacy and enforcement of homeless educational policy.