The obstacles facing homeless children and youth in securing a "free appropriate public education" are truly daunting. The frequent, often forced mobility of homeless families is a major barrier to maintaining their children's attendance at any particular school. The bureaucratic structure of school systems coupled with the multiple demands placed on the parents of homeless children is an additional--sometimes insurmountable--obstacle to school enrollment and attendance. Equally troubling is the prejudice homeless children and youth face in the systems that serve them; such bias often denies them the choices and opportunities afforded other children. This article is an in-depth look into the struggle to improve educational access for homeless children and youth in Chicago. Because Chicago's school system is both massive and bureaucratic, our hope is that the significant success achieved in Chicago through litigation and advocacy will inspire others to confront and work closely with the schools in their communities.