Purpose: In this report, we present the case of a patient with the rare Chilaiditi syndrome, manifesting as episodic abdominal pain that worsened while fasting. Definitive diagnosis of Chilaiditi syndrome requires evidence of the interposition of large or small bowel between the liver and right hemidiaphragm (Chilaiditi sign). Chilaiditi sign is often an incidental roentgen finding in asymptomatic patients. It can be mistaken for pneumoperitoneum, resulting in unnecessary surgery. It can also be mistaken for subdiaphragmatic abscess. Recurrent abdominal pain, distention, vomiting, anorexia, and constipation are typical symptoms of Chilaiditi syndrome. Chilaiditi syndrome more commonly affects males (4:1 male to female ratio), the elderly, and the mentally retarded. Obesity is also a predisposing factor. Case: In the following case, we describe a 55 year old HIV positive gentleman (last absolute CD4 count of 504) with history of gastritis, heavy nonsteroidal anti-inflammatory drug use, hypertension, and anemia presenting with two years of intermittent, crampy epigastric pain that would occur whenever he was fasting. Previous diagnoses included H. pylori-related gastritis and dyspepsia. Symptoms were not associated with fever, chills, weight loss, nausea, or vomiting. However, he has had constipation in the past. Episodes of pain would last two to three hours and resolve spontaneously with no obvious alleviating factors. His daily dose of proton pump inhibitor, esomeprazole, has given him only partial relief. PA and lateral radiographs of the chest showed minimal pleural thickening, and in the right upper quadrant, a loop of transverse colon compatible with Chilaiditi syndrome (Figure 1). There was no acute airspace disease or pulmonary edema identified. This patient has been managed conservatively, and continues to be monitored and evaluated for the possibility of other exacerbating conditions, including peptic ulcer disease.Figure 1: Posterior-anterior chest radiograph revealing hepatodiaphragmatic interposition of the transverse colon (Chilaiditi sign).