Introduction: Chilaiditi’s syndrome was repeatedly an unforgettable case in Emergency Department due to its various symptoms. Methods: This case report consisted two reported cases of Chilaiditi syndrome. Then, we followed the methods of PRISMA for systematic review. Results: In this report, two cases of Chilaiditi syndrome with the different chief of complaint when admitted to the hospital. A 35-yearold woman presented to the Emergency ward with abdominal pain, while the older subject, a 67-year-old man complained of shortness of breath. Plain radiograph showed an elevated right hemidiaphragm and the presence of subphrenic air, making the diagnosis of Chilaiditi syndrome. Both patients were managed conservatively with nasogastric tube decompression and intravenous fluid. The follow up showed favorable results and symptoms resolved. Discussion: Chilaiditi syndrome might not be a rare entity, but a difficult syndrome to identify clinically due to its various unspecific symptoms. The radiological examination was needed to be carried out for the diagnosis. Conservative management led to favorable results. Conclusion: Clinicians should be more aware of the diagnosis of Chilaidity syndrome with its various symptoms. Radiological evidence should be obtained for the confirmed diagnosis, and conservative management was the modality choice. Keywords: Chilaiditi syndrome; radiology; conservative.