Cartilaginous tumors in the head and neck region are rare. We report the case of a middle-aged man with a progressive swelling in the left cheek area who had been seen several times over the years at our otorhinolaryngology department. The progression of the swelling culminated in an extremely large tumor that grossly distorted the patient's face. Examination revealed that the mass had probably originated in the maxillary sinus; it eventually extended to the skull base, middle cranial fossa, and cavernous sinus. Several histologic examinations of biopsy specimens identified the mass as a chondroma. The unusual size and extension of the tumor indicated extensive surgery, but the patient refused. We discuss the natural history of this tumor, and we review the current literature on head and neck chondromas.