Abstract Spontaneous pneumomediastinum is a rare disorder, secondary to lung over-inflation. Patients with this disorder have dyspnea, chest pain, and subcutaneous emphysema. Treatment consists of analgesia, rest, oxygen therapy, and management of the underlying condition. Being a rare disorder, we present two cases of exacerbated asthma complicated with spontaneous subcutaneous emphysema and pneumomediastinum as part of an air leak syndrome. A 2-year-old child with asthma-related subcutaneous emphysema and pneumomediastinum, confirmed with chest computed tomography, treated successfully with conservative management, and discharged on day 8. Another 16-year-old boy with asthma-related subcutaneous emphysema, successfully treated with conservative management, and discharged on day 4. Our air leak syndrome was managed with a conservative treatment, with satisfactory results, avoiding complications of surgical managements. Our case reports focus on topics pertinent to the pediatric generalist, allowing pediatrics colleagues to provide improved care.