Gallstone ileus and Bouveret's syndrome are rare gallstone complications; therefore, their combination is even rarer. The delay of diagnosis is associated with high rates of morbidity and mortality. We reported a 65-year-old woman presented with a three-day history of epigastric and lower right abdominal pain, nausea, and vomiting. A radiopaque shadow was noted on an abdominal X-ray in both the right upper and lower quadrants. In addition to the cholecysto-duodenal fistula, the CT abdomen revealed a combined ileal gallstone ileus with small bowel dilatation and stone in the second portion of the duodenum (Bouveret's syndrome). Initial attempts to extract duodenal stones endoscopically were unsuccessful. Therefore, the patient underwent an exploratory laparotomy and removal of both ileal and duodenal stones. The patient had an uneventful postoperative course. Serious complications include obstruction of the gastric outlet or the small intestine due to gallstone ileus, Bouveret's syndrome, or both. Despite the high failure rate, endoscopic extraction of the stone alone or in combination with lithotripsy is the standard treatment for Bouveret's syndrome. Furthermore, surgical intervention is the standard treatment for gallstone ileus. Gallstone ileus and Bouveret's syndrome remain diagnostic and therapeutic challenges, which necessitate an immediate multidisciplinary approach to prevent substantial morbidity and mortality. Further reports or larger-scale studies are encouraged.