An Airfare Junkie’s Guide to Flying for Free

How to find great airline ticket deals online.

by Darius Fisher
how to find great airfare deals online
Photograph: International Living

Ever heard of the Pudding Guy? His name is David Phillips and among airfare junkies who lurk on FlyerTalk.com, 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 these mileage maniacs aren’t trying. And FlyerTalk.com is their home.

I discovered this 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 Running

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 FlyerTalk to learn the basic jargon (Flyertalk.com/glossary). 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 Orbitz.com, which is powered by ITA. Finally, prepare to soar all the way up to elite level status.

Accrue Credit Card Miles

If flying from airport to airport is not how you want to spend a weekend, an easier option is to accrue miles with your credit card. You already know how the system works. You spend money on your card. You earn miles. You redeem the miles for flights. Pretty simple, right?

That’s what I thought until I explored deeper. I found people buying coinage from the U.S. Mint with their frequent flyer credit card. Others were churning cards—opening a card for a specific promotion and then weeks or months later cancelling it and then reopening the card to again cash in on the promotion. And some doing all of the above!

If this sounds appealing to you, check out the FlyerTalk forum “Miles Buzz.” There you’ll find over 250,000 posts about promotions available, all updated by airfare junkies in real time. Nothing gets by these guys.

Getting Bumped Intentionally

Airlines often overbook flights. Their statisticians predict how many passengers will show up at the gate, and they overbook flights to maximize revenue. But when these number gurus fail, airline staff scurry to find passengers willing to board the next flight.

In exchange for this inconvenience, airlines compensate flyers. On a recent flight to London, Virgin offered me a free round-trip ticket to anywhere in the world, a night in a hotel, and meal vouchers if I took a flight the next day. Here are a few tips to getting bumped intentionally.

• Arrive early, be flexible, and ask politely if any volunteers are needed.

• Choose the airline carefully. According to the U.S. Department of Transportation’s February 2010 Air Travel Consumer Report, Delta, Southwest, American, United, and US Airways have the highest instances of voluntary bumpings.

• Travel in the mornings, Sunday evenings, or during holidays to popular destinations. Historically, this is when you’re most likely to get bumped.

First Published January 30, 2012

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