Introduction Gallstone ileus is an uncommon cause of small bowel obstruction; it is a rare complication of calculus chronic cholecystitis which leads to cholecystoenteric fistula and impaction of gallstone in the gastrointestinal tract leading to mechanical bowel obstruction. Our aim is to report the natural history and management of this rare condition in a teaching hospital. Materials and methods It is a retrospective study, where 10 years of data related to the management of intestinal obstruction secondary to gallstone ileus was collected. The cohort included 10 patients, whose demographic data, clinical findings, and management outcomes were evaluated. Results Majority of patients were female (90%, n=9) with a median of 83 years (range 61-96) although 90% of the population were above 70 years. Presenting complaints were mostly pain and vomiting. The onset of symptoms was between two and seven days.The site of obstruction was mostly the ileum (n=9) with the exception of one case in the sigmoid proximal to a benign stricture, and the size of the stone ranged from 2.5 to 4 cm. Moreover, most of the patients had a previous history of gallstone (n=7) with one post-cholecystectomy status. The laboratory investigations in 50% of patients had deranged liver function test (LFT) and acute kidney injury (AKI), and 60% had raised inflammatory markers, namely, white blood cells (WBC) and C-reactive protein (CRP). Intervention as enterolithotomy was the preferred approach (n=8 (two laparoscopic, six open surgery)), and two patients were managed conservatively. The mean postoperative length of stay was 10 days in the open approach and five days in the laparoscopic approach, respectively. Conclusions Elderly female patients are more prone to have gallstone ileus particularly with a past medical history of gallstones, and the preferred management option is enterolithotomy which could be open or laparoscopic depending on the expertise of the surgeon.