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.