Spontaneous submucosal dissection of the esophagus is a rare esophageal disorder which reveals characteristic features on radiologic and endoscopic examinations. It usually presents with acute epigastric pain, typically accompanied by dysphagia and odynophagia. We experienced a case of a 56-year-old man complaining of chest discomfort and right upper quadrant abdominal discomfort. The findings of upper gastrointestinal endoscopy and barium esophagogram were compatible with submucosal dissection of the esophagus. Chest CT scan showed multiple ulcers that formed a longitudinal tunnel canal. The patient was managed conservatively with nothing by mouth and intravenous hydration. Forty days after the first upper gastrointestinal endoscopy, the patient's symptoms disappeared completely and the massive dissection of the esophagus was much improved except for slight depression on the upper esophagus.