Accidental migration of the chest tube into the trachea or esophagus in pleural drainage is rare. Here we report two patients having different events. The first patient had a chest tube penetrating through an unhealthy right main bronchus into the distal trachea following a right thoracotomy for resecting a lately diagnosed perforating esophagus. The other patient had a chest tube migration into the esophagus following thoracoscopic esophagomyotomy for esophageal achalasia. In these two patients, we used step-by-step tube withdrawal successfully manage these rare events. Based on our experiences, when facing the accidental migration of a chest tube into the trachea or esophagus, the alternative option of step-by-step tube withdrawal could be used before considering aggressive surgical intervention.