Gallstone ileus is a relatively rare complication of cholelithiasis, and an uncommon cause of small bowel obstruction most commonly seen in elderly and debilitated people with associated comorbidities. Symptoms of gallstone ileus are insidious and may be vague while the delay in diagnosis results in a high mortality rate. Herein we report two cases of gallstone ileus in elderly patients with complex medical history who presented at the emergency department with abdominal pain and distension, vomiting and fluid/electrolyte disorders due to cholecysto-enteric fistula and bowel obstruction.