How to improve your position in hotels and on planes

Walter, a computer salesman for a Fortune 500 company, never goes to the airport without an assortment from Dunkin' Donuts under his arm. An overreaction to airlines' stingy food servings?Hardly. The Bavarian kremes and chocolate frosteds aren't meant for personal consumption: they're for Walter's friends at the check-in desk. Walter, you see, is a very popular guy at airport counters and with airline VIP clubs around the country. When he arrives for a flight, he plops down the doughnuts (or a box of designer chocolates if he's trying to make a really good impression) along with his ticket and photo ID. The agents get to know Walter, and when flights are overbooked or there's a seat in first class going begging, guess who gets taken care of first?

It's common knowledge that airline and hotel personnel have a degree of discretion in upgrading customers. We spoke with industry insiders to find out how the game works.

Suite Talk

In previous years, when hotel occupancy rates were anemic, guests could negotiate upgrades with ease. Today, the most desirable hotels can be 85 percent full or more, so upgrades aren't handed out as readily. "We can't make a habit of upgrading, so people can't expect it," says Tricia Messerschmitt of Washington's Four Seasons Hotel. "But we do take care of our best clients: those who stay here often or pay rack rates."

The best time to ask for an upgrade isn't when you check in but rather when you book the room, and it's a good idea to call the hotel directly instead of the 800 reservations line. Informing the agent that you patronize other hotels in the chain will strengthen your request. If you once celebrated your wedding anniversary at the hotel, or held a large business meeting there the year before, let them know that, as well. "Make a case for it," Messerschmitt advises. "You only get what you ask for in this world. The worst that can happen is we'll say no or upgrade you for just part of your stay."

Skyway Bribery?

Upgrading policies vary greatly among airlines, and between international carriers and their domestic counterparts. Many domestic airlines may upgrade their elite-level frequent fliers for free or a small fee if they're flying on a full-fare coach ticket or even, in the case of Northwest, if a passenger is making a connection through one of its hub airports. International airlines are less forthcoming, but two types of upgrading go on: there's the discretionary upgrade—rarer now than in previous years—given to pet customers; and the "oversold" upgrade, given to fill available seats in business and first class when coach has been overbooked.

While airlines officially frown on employees' accepting gifts from passengers like our friend Walter, that doesn't mean it never happens. Some fliers go so far as to ask for the names and birth dates of their favorite airline's airport station manager or supervisors and send cards, flowers, or wine. Showing up with a dazzling bouquet or a box of Godivas at the club room can make a favorable impression on the reservationist there, too. After all, what's a $50 box of candy now and then when you're talking about international upgrades worth thousands?

Oversold upgrades are a different story. Here, your attire and looks may be more important than knowing someone at the desk. "We'll check out the people waiting in line and say, 'He looks really well-dressed, or he's cute,' and upgrade him," says one female agent. It helps, too, if you are celebrating a milestone—say, a 25th wedding anniversary (bring your marriage license). And sometimes it's pure whim: "I've upgraded people because we lost their luggage, or they're really tall and I feel sorry for them having to squeeze into a coach seat, or just because they're sweet and charming," one check-in agent admits. And a Lufthansa supervisor once upgraded a passenger to first class simply because she claimed to be a friend of his favorite opera diva.

Roomier Rooms

  • Bribery attempts usually don't work—which doesn't stop people from trying. One hotel reservationist admits, though, that if a guest is so desperate, she'll often return the money and issue an upgrade anyway.
  • It's easier to gain an upgrade on a shorter stay of a day or two rather than a weeklong one. And it's easier whenever the hotel isn't very busy.
  • Members of frequent-stay programs and American Express Platinum card holders sometimes get automatic upgrades and usually receive special consideration.

Superior Seats

  • People ask for upgrades all the time at check-in, some nicely, some not. Nice is better. "Courtesy gets you a long way," one check-in employee says. A good opening line: "Are you upgrading today?If so, I'd like to be considered."
  • Single travelers are much more likely to be upgraded.
  • Have your travel agent choose an airline or a flight that's chronically oversold in economy class, since that's more likely to result in an upgrade.
  • Most U.S. airlines give complimentary coupons good for upgrading full-fare coach tickets to their very frequent fliers. Anyone can buy such coupon booklets, usually applicable to non-discounted fares.