Spontaneous pneumomediastinum (SPM) is a rare, generally benign condition in young children caused by alveolar rupture and dissection of air into the mediastinum and hilum. In children, SPM is seen most commonly in asthmatics but may also occur in any patient who induces a Valsalva maneuver, including coughing, forceful vomiting, or first-time wheezing. There are limited reports on SPM in first-time wheezing episodes. We report a case of a 4-year-old girl with no history of wheezing who presents with wheezing, mild respiratory distress, and salient radiographic findings of pneumomediastinum, including spinnaker sail sign and continuous diaphragm sign. The SPM is generally a benign entity that requires supportive care, and resolution occurs spontaneously. This article will allow the clinician to become familiar with the specific clinical and radiological signs associated with SPM.