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How to Fly for Free
Power Trip · November 15, 2002

This column regularly dispenses advice about how to cut costs when you travel by air — an important public service during these cash-strapped times. But wouldn't you really rather travel for free?

Below are some strategies on how to do this, as well as tips from people who make a career of it.

First, meet Mark Talbot, a cinema advertising technician from Shelton, Conn. He hasn't paid for a plane ticket in years. How does he do it? "I work all the angles," he explains.

For example, he switches bank cards regularly in order to accumulate more frequent-flier miles. He's carried a Diners Club card, plus affinity cards offered by Hilton, Continental Airlines, US Airways and American Airlines, in the past. "Presently, I'm carrying Delta's American Express card until January, when the annual fee comes up for renewal. Then I'll apply for another Hilton card to get the enrollment bonus again," he says.

Right here is where I get into my caveats. There are many paths to a free ticket, but not all of them are appropriate for a business traveler. Talbot leverages his miles skillfully — more on his strategies in a minute — but I wouldn't recommend every freebie-finding strategy in the book if you're a road warrior.

For example, consider the case of David Phillips, a Davis, Calif., civil engineer who bought $3,140 worth of diet pudding cups and redeemed the coupons on the boxes for 1.25 million frequent-flier miles. Phillips became an overnight media star for figuring out how to beat the system. But buying diet pudding isn't practical for most business travelers.

So before we get into the "how" of snagging a free flight, let's review three rules for reaching your goal:

If it's more expensive to collect the points, pudding boxes, miles or vouchers needed to fly free, don't do it. And by expense, I mean money, but also time. You have to consider all costs when you're gunning for a freebie. Sometimes amassing all the proofs-of-purchase just isn't worthwhile, when you consider the overall price.

If getting a free flight interferes with your business — either taking you out of the way of your destination or preventing you from getting work done — then forget it. Leisure travelers and mileage-collecting hobbyists can afford to go out of their way to get a "fly free" coupon. Not you. Collecting a free ticket is a secondary consideration, not your reason for traveling. So keep your priorities straight.

If getting a gratis flight means bending the truth, telling a little white lie or embellishing the facts, don't walk away — run. True for anyone? Yes, but especially when you're traveling on behalf of your company. Because you aren't just damaging your own credibility; you could also endanger any pricing agreements your company has with the airline.

All right, so how do you get a free ticket? Here are three proven strategies for corporate travelers:

1. Get "bumped" from your next flight. The technical term for it is "denied boarding," which means that your airline booked too many people on your flight. It happens constantly. Airlines use sophisticated software that predicts how many passengers will actually show up for a flight, allowing it to overbook its planes. It usually works, but sometimes the software miscalculates, leaving some passengers stranded. Denied boarding comes in two flavors: involuntary (meaning you've got no choice) and voluntary (meaning you offered to give up the seat). The reward — or compensation — is usually a free ticket. You can find out which airlines overbook the most at the U.S. Department of Transportation's Web site. Click on "Air Travel Consumer Report" and then on "Oversales."

Brian Todd, a lobbyist in Bakersfield, Calif., maximizes his bumping opportunities when he flies on United Express commuter planes in the Golden State. "These things are constantly getting oversold, but United handles it beautifully," he says. "Passengers who agree to give up their seats each get free round-trip tickets on United to anywhere they fly in the 48 states. I just listen closely to the gate announcements, and when I hear such an offer, I pounce. It rarely means more than a two-hour delay, and they buy you a meal to boot." Todd paid for this year's vacation through "denied boarding" coupons.

2. Rack up the miles. Let's get back to Mark Talbot, our mileage collector. The key to his success isn't in doing anything for miles, but doing everything within reason in order to amass them. Miles are a fact of life for business travelers, and you either play the mileage game to win or you don't play it at all. Talbot clicks on discussion groups that reveal new mileage-collection strategies — one favorite is Randy Petersen's FlyerTalk forum — and scans through all the postings. (I've also weighed in on how to run up the points in a recent column, "5 rules for collecting frequent-flier miles.")

Some of the tactics used by road warriors are pretty elaborate. Gary Steiger, a mileage-collector in Ross, Calif., has his own favorite methods for getting free miles. Among them: Moving money within brokerage accounts (every transfer comes with a mileage bonus), acquiring free credit cards with upfront miles and using them for every purchase possible and, of course, changing long-distance phone service every six months. Do they work? "I paid no money for my last five international round trip flights, and I have over 341,000 miles, plus two tickets for domestic travel still waiting to be used," he says. I would say that's a "yes."

3. Complain — when you have good reason to. The airlines aren't going to like this one, but it works. And before I proceed, here, let me refer back to the third rule listed above: no lying! If you've had a genuinely bad customer-service experience, a carefully worded grievance can land you a free ticket. When should you ask for a freebie? Generally speaking, the airline has to really screw up in order to offer you a ticket. If you're denied boarding without a valid reason, or your valuable luggage is lost — these are freebie ticket offenses. But they're few and far between.

How do you go about asking? The best way is to write to the airline's customer service department. Write a real letter, not a fax or an e-mail. Include your flight number, your name, record locator number and the date that you traveled. Describe the problem briefly. Tell the carrier what you want in the way of severance (e.g., a free ticket). In order to underscore that you mean business, send a carbon copy to the U.S. Department of Transportation's Aviation Consumer Protection Division. (For more info, go to the DOT aviation Web site and click on "Air Travel Problems & Complaints.") These are the folks who register airline complaints. Then certify the letter so that you know when it's received.

I've described the three most popular ways to get a free airline ticket. But there's more, of course. In future columns, I'll review other strategies for securing non-revenue airline tickets. I'll also show you how to get other things for free, from hotel rooms to rental cars.

There may be no such thing as a free lunch. But travel? That's another story.

Christopher Elliott is a travel writer based in Key Largo, Fla. This column also appeared on Microsoft's bCentral site.