Peer support groups have been an increasingly popular way of limiting the adverse effects of life with a chronic illness for adolescents although few groups have been rigorously evaluated. This paper reports the findings of a realistic evaluation of a hospital based peer support program Chronic Illness Peer Support (ChIPS), in Sydney, Australia. We collected qualitative interview and focus group data from four participant groups; new ChIPS members, their parents, older members who had been in ChIPS for two or more years, and ChIPS co-ordinators past and present. Results of qualitative data have been aggregated and organised into three categories; program attendance: getting in and staying in; program outcomes for young people: personal growth and development; and social connection. Questionnaires were also administered to fourteen new ChIPS members but no significant changes in distress or self-esteem were recorded between the beginning and the end of the short study period. The ChIPS Introductory Program fulfilled its aim, entering young people with chronic illness into the peer support program. There was evidence of initial personal growth and development in those young people, with potential for enhanced social connection from ongoing participation in ChIPS activities.