Along with rapid population aging, the importance of chronic disease management increases with high growth of national healthcare expenditures, and efficient spending on healthcare is required to reduce unnecessary utilizations. For that reason, this study examined the association of annual healthcare expenditure with age and disease duration of chronic patients. Furthermore, the study investigated the effect of usual source of care (USOC) to suggest directions for preventive management of chronic disease. Using Korean Health Panel Study data, this study selected 1481 outpatients, who had out-of-pocket costs for hypertension or diabetes, and their total healthcare and chronic disease management (CDM) costs were examined. With patient aging, CDM cost decreased while the total healthcare cost increased, but longer duration of hypertension or diabetes resulted in increases in both CDM and total healthcare costs. In addition, the moderating effect of USOC indicated that elderly patients had increased CDM costs when they had a regular site for healthcare. In contrast, patients with longer duration had reductions in both CDM and total healthcare costs while having a regular doctor increased CDM cost. The results of this study could be an evidence for future policies to suggest proper preventive management plans for specific subjects.