Invasive pulmonary aspergillosis (IPA) has been reported to occur secondary to coronavirus disease 2019 (COVID-19), and the condition has been termed COVID-19-associated pulmonary aspergillosis (CAPA). We diagnosed two severe COVID-19 cases with multiple cavitary lung lesions and chronic pulmonary aspergillosis (CPA) on days 58 and 48 of admission, respectively, with gradual improvement in the respiratory status. Both patients were positive for Aspergillus-precipitating antibodies (APAb). We chose oral itraconazole (ITCZ) for both patients because of its convenience in terms of long-term treatment. Cavitary lesions diminished after ITCZ administration. The risk factors for pulmonary aspergillosis in both patients were determined to be steroid pulse therapy, use of baricitinib, diabetes mellitus (DM), ICU admission, long hospital stay, and the use of broad-spectrum antibiotics. Pulmonary aspergillosis must be suspected in patients with severe COVID-19, even if they are asymptomatic, because not only IPA but also CPA can occur following COVID-19. Therefore, oral ITCZ may be a treatment option for CPA following COVID-19.