[Figs]

Planes were capable of being flown autonomously in the 1980s. In particular, the Soviet's space shuttle, Buran, performed unmanned orbital maneuvers and landing during its 1988 test flight.

http://en.wikipedia.org/wiki/Buran_%28spacecraft%29

So, the technology to do these kinds of things has already been done before (though unfortunately neglected!). I think the main challenge is just convincing people that it's safe enough that they will be willing to buy tickets.