Introduction Spontaneous cholecystoduodenal fistula is a rare complication of the gallbladder calculosis. Bowel obstruction is the complication in less than 1% of these patients. The pathognomonic triad (Rigler triad) of pneumobilia, small-bowel distention, and ectopic gallstones is typical for gallstone ileus. In only 1-3% of the patients with bowel obstruction by ectopic gallstone the localization of obstruction is in the duodenum, and it is called Bouveret syndrome. The rarest complication is a floating non-obstructing gallstone trapped in the stomach. Outline of cases We present three elderly female patients with persistent abdominal pain and known gallbladder calculosis in the patients' histories. Plain radiography of the thorax and abdomen and ultrasound were performed as the first choice and contrast-enhanced computer tomography (CT) was done subsequently. In the first patient, CT and magnetic resonance imaging (MRI) showed signs of pneumobilia, cholecystoduodenal fistula, and the presence of the gallstone in the stomach. The iodine contrast X-ray swallow test revealed a cholecysto-duodenal bulb fistula and floating calculus in the stomach, confirmed by endoscopy. In the second patient with persistent abdominal pain, CT and barium swallow test showed signs of pneumobilia, cholecystoduodenal fistula, and two ectopic gallstones obstructing duodenum-Bouveret syndrome. The third case showed signs of the Rigler triad-typical signs of gallstone ileus. Conclusion Spontaneous cholecystoduodenal fistula is a rare condition with possible complications such as Bouveret syndrome, gallstone ileus and floating, non-obstructive gallstones in the stomach, as the rarest possible complication. CT, MRI with magnetic resonance cholangiopancreatography, as well as the contrast X-ray swallow test can be very helpful in the detection of the bilio-enteric fistula and ectopic gallstones.