Disease-related pain and the consequences of pain in children and families are important areas for further research inquiry. There are limited data on the relationship between children’s emotional well-being, their experience of pain, and the strategies they employ to cope with pain within the context of serious medical illnesses. Understanding what strategies chronically ill children use to cope with pain and stress is essential for clinical intervention. This observational study examined the ways that children and adolescents with chronic diseases cope with pain and adapt to illness. The data were collected by self-report measures and projective drawing techniques in a novel way to assess the emotional functioning in a mixed cohort of youth with disease-related pain (oncological, rheumatic, and cystic fibrosis). This protocol was administered to 47 children, aged 7-14, recruited from pediatric wards of hospitals of Trento and Rovereto (Italy). The results showed that coping strategies in youth with disease-related pain differed across diagnoses and with self-representations (as part of the self-concept adaptive mode). We also provide evidence of the applicability of using projective drawing methods in assessing coping in youth with chronic illness and associated pain.