With one exception, I have never received a hotel upgrade without asking for it. The more you ask, the better your chances become.
Don't kid yourself: those chances are fairly slim, whether you're asking at the Trump International Hotel and Tower in Chicago or a well-worn four-star hotel in a smaller city. But at times, persistence pays off.
Don't confuse persistence with pestering. Asking 21 times and annoying everyone from the hotel operator to the general manager is neither good strategy nor proper manners.
However, there are three occasions when a polite inquiry about upgrade opportunities can be effective.
The first should be made when you make the reservation. The second inquiry comes when you confirm your stay with the hotel a day or two before arrival. The third should come at check-in.
By the time you walk up to the desk, they know you want a hotel upgrade and that you've been persistent but not obnoxious. You're a realistic budget traveler. Click "next" and consider that realism in a different context.
