Not really. As the consumer, you don't pay $30 for a stock that's trading at $20. What you are referring to is when a company pays over the enterprise value for another company. This does regularly happen, since synergies can sometimes justify this.
Sorry if I was unclear -- I was talking about airfare, not mergers and acquisitions. My point is that even if people can fly LAX-NYC for $x or they can buy 25,000 miles for $x-10 and use those miles to fly LAX-NYC, many people will still buy the revenue ticket. By the "corporate context" above, I meant corporate travel. But this happens even among leisure travelers.
Your statement that "no one would ever pay more than the cost to purchase [miles] outright" assumes people are (a) rational, and (b) have perfect information. Both of those assumptions are often wrong in the real world.
All of this also ignores the fact that booking an award ticket comes with additional annoyances and restrictions. But even assuming booking award tickets and buying miles do not entail any additional transaction costs over buying a revenue ticket, I still stand by my statements.
