The transition process to adulthood is a challenging but crucial period for the future well-being of patients with chronic diseases. The objective of this study was to evaluate whether specific clinical variables and disease activity status are associated with improved transition readiness among patients with juvenile idiopathic arthritis (JIA) and their parents. JIA patients aged 12–18 years were enrolled in this cross-sectional study. Patient characteristics and laboratory data were collected, and disease activity was assessed using the Juvenile Arthritis Disease Activity Score (JADAS-10 and JADAS-27). All patients and their parents simultaneously filled out the Serbian version of the Transition Readiness Assessment Questionnaire (TRAQ). A total of 91 JIA patients (of them 27 males, and 64 females; median age 15.32 years, range 11.58–18 years) along with their respective parents were enrolled in the study. Our results demonstrated that increased patient age and use of biologic therapy, particularly etanercept, were significantly associated with higher TRAQ scores and improved transition readiness in both JIA patients (p < 0.001; p = 0.038) and their parents (p < 0.001; p = 0.035). Patient and parent TRAQ scores showed a strong positive correlation (ρ = 0.676, p < 0.001). No significant associations were found between other clinical variables (gender, JIA disease subtype, disease duration, disease activity status, extraarticular comorbidities, and autoimmune diseases in the patient’s family) and transition readiness. Older patient age and the use of biologic therapy, particularly etanercept, are positively associated with transition readiness in both JIA patients and their parents.