This dissertation examines the gender differences among the homeless. Although women with dependent children comprise the fastest growing subgroup among the homeless population, most of the homeless are still single adults. The vast majority of these single adults are men, though the number of single women has increased notably in recent years. The second purpose of the dissertation is to examine who is most vulnerable to homelessness. The analysis strategy was to examine the literal homeless comparing three subgroups, unattached men, unattached women, and women with dependent children, and then to examine the very poor who are housed comparing the corresponding subgroups. Comparisons were made of the characteristics of and the financial and social resources available to the literal homeless and the domiciled poor. The descriptive analysis of the gender differences among the homeless are based on empirical data collected from the Chicago Homeless Study in 1985. Data on unattached men and women who are housed come from the General Assistance Study conducted in Chicago in 1984 and data on women with dependent children come from a 1985 study of welfare families in Chicago. The findings indicate that homeless men are poorer, more disabled, and more socially isolated than homeless women. In particular, their levels of poverty, disability, and social isolation are substantially higher than that of homeless women with dependent children. Their high levels of disabilities make it extremely difficult for the homeless men to find employment or to reciprocate in social relations. Most of them have had their social networks destroyed or exhausted and few receive needed social services. The absence of social and public resources means that homeless men have difficulty extricating themselves from homelessness. For these reasons, the men are more vulnerable to chronic homelessness. There is a subset of homeless single women whose conditions are not very different from homeless men. Women with dependent children have the best chances of extricating themselves from homelessness. Policy implications are discussed.