According to Boyle’s law, as the pressure falls, the volume of gas rises in an inversely proportional manner. This means that during an aircraft flight, the volume of trapped air in gas filled body chambers will increase. As a consequence, it is fairly well established that individuals with an untreated pneumothorax should not participate in commercial flying due to the risk of it enlarging and the possible development of tension. However, whether this also applies to individuals who have a long-standing, clinically stable pneumothorax is uncertain. The following article describes two adult patients each with a chronic pneumothorax who asked whether they would be fit to fly in an aircraft. We outline their histories and subsequent evaluation which consisted of clinical assessment, computed tomographic imaging, a hypoxic challenge test and exposure to a hypoxic hypobaric environment in a decompression chamber.