Tumors of the trachea are rare and create signs and symptoms that mimic common upper airway diseases. A tracheal mass is not usually considered in the clinical differential diagnosis of an affected patient and is often overlooked on chest radiographs. The purpose of this article is to prompt earlier diagnosis and improve long-term survival of patients with a tracheal tumor through the presentation of the salient clinical, pathological, and radiological features of a variety of benign and malignant tracheal diseases.