Chilaiditi's sign is a rare radiological finding in which a portion of the colon or small intestine is interposed between the liver and right hemidiaphragm. We present a 28-year-old male who came to the emergency room with nausea and vomiting. A computed tomography scan without contrast of the abdomen and pelvis showed a new focus of air in the perihepatic region, suggesting a pneumoperitoneum or a loop of bowel. Exploratory laparotomy was pursued but deferred after a multidisciplinary review of the imaging. A decision was made to pursue conservative management with a diagnosis of Chilaiditi syndrome. This case illustrates the importance of maintaining a broad differential when approaching a patient with abdominal distress and possible pneumoperitoneum, especially when the clinical picture does not align with radiological findings. Early consideration of Chilaiditi syndrome is important to minimize unnecessary surgical intervention such as laparotomy or further endoscopic intervention, which may lead to potential complications such as perforation, bowel wall ischemia, or respiratory failure.