A schwannoma is an uncommon benign orbital tumor that arises from Schwann cells in the peripheral nervous system. Schwannoma with cystic degeneration is an even more rarely reported entity. Clinical examination alone is inadequate for the diagnosis. Radiological examination, like computed tomography (CT) scans, can help in the diagnosis; however, the diagnosis can only be confirmed by histopathological examination (HPE) after excision biopsy. Here, the authors report four cases of orbital schwannoma with cystic degeneration that presented with proptosis and decreased vision. CT scans showed a well-defined non-enhancing intraconal mass with cystic spaces. The histopathological examination was diagnostic for orbital schwannoma with cystic degeneration. Schwannoma should be included in the differential diagnosis of cystic orbital lesions.