Infectious mononucleosis (IM) caused by Epstein-Barr virus is a self-limiting condition and usually carries a benign course. It is usually seen in adolescents and young adults. However, complications can occur in a small percentage of patients such as splenic rupture, myocarditis, and meningitis. Tracheal obstruction as a result of IM is extremely rare. In this case report, we highlighted a rare complication of nearly fatal tracheal obstruction in a young patient of IM that was managed timely by emergency tracheostomy.