Gallstone ileus is rare complication of cholecystitis or cholelithiasis due to the formation of an aberrant communication between the gallbladder and small bowel. The movement of the gallstone to the small bowel may cause bowel obstruction. A patient presented with acute onset abdominal pain, nausea, vomiting, and tenderness around the umbilical area. Physical exam, laboratory tests, and computed tomography were performed. Within 24 hours the patient had developed peritonitis. He received an emergency exploratory laparotomy, and small bowel resection and anastomosis of the proximal jejunum. The patient had gallstone ileus complicated by the presence of an intraluminal abscess and perforation due to pressure necrosis caused by the gallstone. The patient recovered and was discharged on postoperative day 31. Despite having had a cholecystectomy 20 years prior this case highlights a patient who suffered a rare case of gallstone ileus.