An 11-year-old girl with no significant medical or ocular history presented to the emergency department with asymmetrical eyelid swelling for 2 days. She was noted to have eyelid crepitus on examination. The patient reported a prolonged episode of crying followed by chest pain and dyspnea that resolved prior to her presentation. Both face and chest CT showed extensive air tracking in the subcutaneous tissues of the neck and face and pneumomediastinum without pneumothorax. The patient was discharged home without further intervention. On follow-up 1 to 2 weeks later, she had complete resolution of her symptoms. While pneumomediastinum is extremely rare in the pediatric population, it can be considered in the differential diagnoses of eyelid swelling and crepitus in the appropriate context. To this author's knowledge, this is the first pediatric case of pneumomediastinum with an initial presentation of eyelid swelling.