When looking at the last fifty years as an era in air transportation one cannot but conclude that significant advances have been made. Speed, capacity, cost, safety, and environmental impact, all improved measurably during that period. This improvement was so significant that it almost masks the difficulty trade-offs that are often faced when trying to enhance any one of these indicators. However, an examination of the rate at which technological innovations has come into the system, leads to the conclusion that there has been little by way of breakthrough for at least a decade. What does this say about what to expect in the next fifty years of air transportation? Is the system ripe for a major breakthrough, and if so where will it come from? This essay proposes some answers to these questions, and suggests that the breakthroughs are likely to arise in the way the system is managed and regulated. The next phase in the development of the system could be characterized by economic, institutional, and regulatory frameworks enabling technological innovations rather than the other way around.