Older adulthood (i.e., 60 years of age and older) is associated with a worsening in happiness-contributing factors, such as one’s physical health. For example, older adults experience elevated rates of chronic pain (i.e., pain that persists for more than three months). Despite the decrease in happiness-contributing factors, older adults experience higher levels of subjective well-being (i.e., eudaimonia) compared to their younger counterparts. This phenomenon is known as the well-being paradox. While the paradox has been well established, little is known about the role of chronic pain in relation to the experience of the paradox. This study is, therefore, aimed at investigating the influence of chronic pain and its associated characteristics on the well-being paradox. Findings were derived from 132 participants from Canada ranging from 60 to 90 years of age living with chronic pain. Results were obtained from a set of self-report questionnaires analyzed using a series of multiple linear regressions. Analyses revealed that current age, magnification, and psychological inflexibility significantly predicted overall eudaimonic well-being. Further, three subcomponents of eudaimonic well-being were analyzed (i.e., self-acceptance, autonomy, environmental mastery). Current age, developmental age, physical functioning, helplessness, and psychological inflexibility significantly predicted participants’ self-acceptance. Current age, magnification, and psychological inflexibility significantly predicted autonomy levels. Finally, current age, developmental age, physical functioning, helplessness, and avoidance of pain significantly predicted participants’ environmental mastery. Aside from adding novel contributions to literature concerning the well-being paradox, findings from this study could influence training for mental health professionals and result in improved chronic pain treatments for aging populations.