This morning’s New York Times piece on hotel room upgrades offers some basic advice. My favorite:

Randy Petersen, publisher of Inside Flyer, a magazine that covers travel-loyalty programs, suggests making a joke of your request. “You can say, ‘By any chance, is that big presidential suite available? I just feel important tonight,’ ” he said. But, he added, “You shouldn’t demand it or tell them it’s your entitlement.”

It happens most frequently though when you

check in very late when all the other rooms might just be gone.

A single night stay, late check in, often means that they can give you the upgrade without tying up the room that they might otherwise sell to a higher paying guest. When the room would otherwise go empty, it’s a costless perk for the hotel to deliver. So that’s when it’s given away most frequently — but ironically that’s when there’s no time to enjoy it!