Chilaiditi's sign (colonic interposition) is a rare anomaly due to an abnormally located portion of the colon that is interposed in between the liver and the diaphragm. This rare anomaly is often incidentally seen on chest or abdominal radiographs. Chilaiditi's radiographic sign is usually asymptomatic, whereas the medical condition accompanied by clinical symptoms is termed Chilaiditi's syndrome. Possible causes of the syndrome include a long and mobile colon, scarring of the liver (cirrhosis), ascites, long-standing lung disease, as well as laxity of the falciform ligament. The most common clinical signs of Chilaiditi's syndrome include gastrointestinal symptoms; however, clinical presentation can vary. This report describes a case of a 21-year-old male patient who presented with a longstanding history of left upper quadrant epigastric abdominal pain with diarrhea (six to eight loose watery stools). The patient was diagnosed with Crohn's colitis and had tried a myriad of medical therapies with no adequate response. He chose to seek a second opinion and was subsequently discovered to have Chilaiditi's syndrome via computed tomography (CT) and confirmed by barium enema. The patient then elected to undergo a right laparoscopic colectomy to resolve the symptoms. By postoperative day five, all symptoms had resolved including abdominal pain and diarrhea. Therefore, it is important to consider Chilaiditi's syndrome as a differential diagnosis in persons presenting with left upper quadrant pain and symptoms of Crohn's colitis, especially those treated with adequate medical therapy without alleviation of symptoms.