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Tell him to cancel and send you the cash. Rebook on his behalf, and put his name on the reservation alongside yours. He'll get the upgrade, free breakfast and if you have an ambassador you can get him surprise beers/wine on arrival. You will then get the room points...
Do you have an ambassador? Doesn't hurt to try and ask that route.
I'm sure if you offer to pay they will
They sent up free champagne, it was really easy. Great job Sheraton chicago!