Individuals from all segments of society are affected by homelessness – the old and young, men and women, single individuals and families. The majority of individuals will experience homelessness only on a short-termed basis. However, about 10-20% will experience homelessness for years. Although, the chronically homeless represent only a fraction of the total homeless population, they utilize the majority of resources available. Current literature has focused primarily on other groups within the homeless community, leaving little to be known about the chronic homeless. Without a better understanding of this unique group, interventions can only be based upon assumptions. The purpose of this descriptive phenomenological study was to better understand the experience of illness in the context of being chronically homeless. Twenty chronically homeless individuals shared their experiences of being ill while living on the streets. These individuals participated in private, audio-taped interviews in order to explore their daily struggles while being sick. The individuals identified barriers as they attempted to access health care and recover from an illness. Themes that were identified from this study were: (a) trying to survive, (b) access to care, (c) being stigmatized, and (d) trying to be healthy. Each of these themes were further discussed in detail and compared to other published literature. This information can be helpful, not only for policy makers, but for other health care workers as then plan for future interventions to provide appropriate care directed at the chronically homeless.