Mental health concerns have been well studied among youth experiencing homelessness, yet few studies have explored factors that contribute to well-being in this population. The current cross-sectional study examined rates and correlates of well-being among youth experiencing homelessness. This is a descriptive, secondary analysis of the baseline data from a clinical intervention study. Ninety-nine youth (aged 16−25) who were experiencing homelessness were recruited in Chicago. Approximately 40% of the sample reported average or above average well-being relative to existing benchmarks. Having medical insurance, a mobile phone, and a history of more severe childhood trauma were unique cross-sectional predictors of worse well-being (all ps < 0.034). A significant portion of our sample experienced well-being. Having access to certain resources may be counterintuitive indicators of poorer well-being among youth experiencing homelessness, perhaps because they are indicators of greater need or increased social comparison among these youth.