Homeless children tend to experience a variety of academic problems, and little is currently known about this growing segment of the American population. This study was undertaken using administrative data from the Chicago Public Schools (CPS) and a program that serves many of Chicago's most vulnerable homeless families to examine children's educational experiences. Qualitative data from interviews with key informants were used to help place the findings from the quantitative analysis in context. Conclusions drawn from the analysis of results include: (1) Homeless children experience a considerable amount of school mobility; (2) Many homeless children struggle academically; (3) More than 20 percent of homeless children are identified as having special education needs; and (4) Very few homeless children are able to take advantage of opportunities to attend schools other than neighborhood schools. Results have implications for how public schools and homeless shelters can work together to improve homeless children's educational outcomes. (Contains 32 footnotes, 9 figures, and 36 tables.) [Financial support provided by the Bowman C. Lingle Trust.]