Chondrosarcoma is a cancer of cartilage cells, and despite being a common primary bone tumor, tracheal chondrosarcoma is rare with only 18 cases reported in the literature prior to mid-2016. A 60-year-old gentleman presented with progressively increasing cough, severe stridor, and production of phlegm for approximately 2 years. On admission to our tertiary care hospital, he developed complete obstructive apnea within an hour, and was intubated. A tracheal biopsy was performed, followed by resection. Histopathology confirmed chondrosarcoma of the trachea. The patient tolerated the procedure very well and is currently symptom-free on follow-up, with no signs of recurrence.