The Chilaiditi syndrome is when the radiologic Chilaiditi sign, defined by the interpositioning of the colon between the liver and diaphragm, becomes complicated by clinical symptoms such as respiratory insufficiency or bowel obstruction. We present the case of a 70-year-old male with a history of depression, anxiety, gastroesophageal reflux disease (GERD), and post-polio syndrome, who presented with left shoulder pain, chronic weakness, and dizziness. Initial evaluation revealed hypotension and elevated lactic acid, attributed to dehydration. Further imaging identified a Chilaiditi sign, thus raising suspicion of small bowel obstruction and the Chilaiditi syndrome. Despite conservative management, the patient continued to experience elevated lactic acid levels, prompting a computed tomography (CT) angiogram to rule out bowel ischemia. No acute intra-abdominal pathology was identified, and the patient improved with hydration and bowel rest. This case highlights the challenges in diagnosing and managing the Chilaiditi syndrome in the setting of chronic comorbidities.