Chronic pain rehabilitation helps to reduce pain and restore valued life roles. Patients may have more positive outcomes when they perceive rehabilitation to be personally meaningful. This study examined associations between self-reported, personally meaningful rehabilitation and well-being. A pilot study was conducted using an online survey of people with chronic pain and experiences of rehabilitation. The PROMIS Pain Interference Short Form 8a and The Flourishing Scale were used to explore well-being. A modified self-report measure, the Meaningfulness in Rehabilitation Scale, was pilot-tested for construct validity and used in the survey. Of the 48 participants (81% female; 19% male), most attended a generalist therapy practice (62%) once per week (33%) or once per fortnight (29%). No statistically significant relationship was found between self-reported meaningfulness in rehabilitation and pain interference or other patient and therapy characteristics (duration of chronic pain category, type of therapy practice, resolution of rehabilitation category, and frequency of appointments). The nonparametric analysis identified a statistically significant moderate positive correlation between self-reported meaningfulness in rehabilitation and the flourishing aspect of well-being. This raises important questions and suggests that patients' perception of rehabilitation as meaningful warrants further research. This pilot study provides valuable guidance to inform a larger investigation.