Objective There has been much newspaper and online news coverage of in-flight obstetric births on commercial aircraft over several decades. This case series reviews several cases of in-flight birth and immediate maternal and neonatal outcomes from air medical retrievals in the Northern Territory of Australia over a 3-year period. Methods This is a retrospective written case note and electronic medical retrieval record analysis of 4 patients undergoing in-flight, at altitude, obstetric birth. Results Four premature births are recorded by CareFlight Operations over a 4-year period from January 2011 to January 2015. All patients involved were preterm; term ranged from 22 weeks to 36 weeks. Tocolysis was implemented on all 4 patients according to local obstetric guidelines. Maternal complications included 1 patient suffering antepartum hemorrhage and 2 patients suffering postpartum hemorrhage. Three neonates born at altitude needed neonatal resuscitation including positive-pressure ventilation. One neonate, 22 weeks’ gestation, died approximately 2 hours after delivery. Maternal follow-up showed no morbidity or mortality at 1 to 6 days after birth. Conclusion In-flight deliveries are rare events in air medical medicine. This case series includes patients of variable preterm gestation and correlates poor outcomes to prematurity of neonates. Close communication between remote clinics, obstetric centers, and air medical teams plus up-to-date early labor guidelines are essential for safe practice and to limit the risk of in-flight births.