Measles remains a major global public health challenge as declining vaccination coverage fuels outbreaks worldwide. Although pneumonia is the most recognized respiratory complication, spontaneous air leak syndrome—including pneumomediastinum, subcutaneous emphysema, and pneumoperitoneum—is rarely documented. We report the case of a 9-year-old previously healthy girl with no documented measles–rubella vaccination who presented with fever, maculopapular exanthem, Koplik spots, and persistent cough. Measles was confirmed by both immunoglobulin M enzyme-linked immunosorbent assay and real-time reverse transcription polymerase chain reaction. She developed sudden cervicothoracic swelling and chest pain. Chest radiography revealed pneumomediastinum and subcutaneous emphysema; computed tomography confirmed extensive air leak including left pneumothorax and pneumoperitoneum. Flexible bronchoscopy and upper gastrointestinal endoscopy excluded structural airway and esophageal injury. Laboratory evaluation revealed elevated hepatic transaminases, gamma-glutamyl transferase, lactate dehydrogenase, and D-dimer. Conservative management with high-flow supplemental oxygen and clinical surveillance led to progressive resolution. The patient was discharged on hospital day three, asymptomatic and breathing room air. This case highlights the spectrum of air leak complications in measles and supports conservative management in hemodynamically stable pediatric patients when structural injury has been excluded.