Tracheal diverticulum is a rare clinical entity. It can be caused due to either congenital or acquired weakness of the tracheal wall. A tracheal diverticulum is usually asymptomatic or present with non-specific symptoms like pharyngeal discomfort and cough. Diagnosis is confirmed using computed tomography, showing the presence of paratracheal air collections. Sometimes, communication between tracheal lumen and cyst can be visualized. In general, conservative treatment of symptoms is proposed although there is no consensus about it. We report a case of a middle-aged man presenting with progression of chronic cough and recurrent respiratory infections. A diagnosis of tracheal diverticulum was made based on a computed tomography, revealing typical right-sided dorsolateral paratracheal cysts with suggestion of tracheal communication.