The displacement and trapping of the colon between the liver and the right hemidiaphragm are known as the Chilaiditi sign or syndrome. The Chilaiditi sign presents in an asymptomatic patient, while Chilaiditi syndrome presents with symptoms such as abdominal pain, distension, and constipation, in addition to complications such as perforation, volvulus, and bowel obstruction. It is often misdiagnosed as pneumoperitoneum or free air under the diaphragm and liver, often seen on the abdomen and chest radiography. It more commonly presents in males than in females. Here, we present the case of a 37-year-old female who reported abdominal pain and persistent constipation. An abdominal CT scan showed entrapment of a bowel segment, which is referred to as the Chilaiditi sign. The patient's presentation with hepatobowel entrapment and persistent gastrointestinal symptoms was diagnosed as Chilaiditi syndrome. This presentation entails a conservative management approach. The aim of this report is to educate about the rare occurrence of Chilaiditi sign and Chilaiditi syndrome as a differential diagnosis to often misdiagnosed critical conditions such as pneumoperitoneum and intestinal perforation. Correctly identifying these patients will reduce overtreatment and help improve outcomes.