Get an embarrassing (but not offensive) sticker and put it on his flight case and see how long till he notices. My first thought was NAMBLA, but that probably wouldn't go over too well with the company.
Some night when he doesn't have to fly the next day could always set a wakeup call for some ungodly hour. Or call him ever half an hour pretending to be his wakeup call.
Oh...just thought of a good one.
http://www.jetuniversity.com/contact.html on the right side
