Fly Free

Ever heard of the Pudding Guy? His name is David Phillips and among airfare junkies, he’s a legend. In 1999, he spotted a promotion: In exchange for every 10 Healthy Choice brand barcodes it received, the company would reward 500 frequent flyer miles. So he bought 12,150 pudding cups.

A few months later, Healthy Choice sent him 1.25 million frequent flyer miles. The cost was just $3,150. To this day, no one’s ever topped the Pudding Guy and his creamy bounty. But that doesn’t mean the “mileage maniacs” aren’t trying.

I discovered their unusual airmiles discussion board and knowledge base while researching flights to Europe. A simple query brought me to the site, but the airfare expertise of these schemers sucked me in. I soon learned their lingo and some interesting, albeit time-consuming, ways to fly for free and earn perks in the air.

Mileage runners book long, inexpensive flights to maximize frequent flyer miles. So instead of flying from, say, Los Angeles to Chicago, a dedicated mileage runner might add connections in Houston and Atlanta. Or if the price is right, one might take the same flight three times in a day to rack up miles.

The ultimate goal is twofold: Accrue enough miles to travel for free. And, more importantly, vault the mileage runner into the status of airline elite, giving him access to first-class upgrades, the coveted airport lounge, meal vouchers and the pleasure of skipping the security queue.

If you have some time on your hands, figuring out the perfect mileage run is like solving a puzzle. First, head to the airmile website to learn the basic jargon. Then pick the airline frequent-flyer-miles program you’re going to use. Once you’re ready, search for cheap flights from your home city. Next, figure out the full fares and airline routing rules of the flight.

When you’ve found a flight that abides by airline rules, use ITA’s Matrix Trip Planner to build your itinerary and then book your airfare either through the airline or, which is powered by ITA. Finally, prepare to soar all the way up to elite level status.

If you’re a subscriber, you’ve already seen my article on page 12 of the August issue of International Living magazine, where I give full details on the airmiles website, plus other ways to get free flights…and how to get bumped to first class. If you’re not a subscriber, you can become one here.


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