You’re broke. Your woman has left you. But bigger than your heap o’ troubles is a pile of Frequent Flyer miles, sitting in neat, invisible little stacks, to be exchanged for a trip to Hong Kong, Amsterdam or any other far-flung clime with easily accessible and cheap companions.

But with Frequent Flyer programs becoming increasingly impenetrable; with free tickets being harder and harder to come by; with airlines increasingly trying to parlay free ticket requests to be used for hotels and restaurants… how can you guarantee a posh seat on a free jumbo jet?

For your perusal, a six point How-To on securing a coveted free ticket. It’s not fool proof. You might have to steel your gaze and bluff; you may very well have to adamantiumize your sack. But this’ll get you as close to a free ticket as we can get you.

1) Remember the 331st Day Rule. When trying to exchange your Frequent Flyer miles for a free ticket, the inner-most junta of savvy travelers darkly murmur of the infamous 331st Day Rule.

What is the 331st Day Rule? Essentially, that you will be most likely to get one of the small numbers of Frequent Flyer seats on a flight on the first day bookings are available, which is generally 331 days before the flight you want. This is completely arbitrary, except that it appears to be a loose industry standard for the furthest day out possible that you can realistically book a ticket.

2) Do your research. Need we say that, whether you are turning in thick wads of your own cash or the ephemeral, easily deflated currency of Frequent Flyer points, a responsible consumer does their homework?

Your first step when trying to find that juicy, much coveted Frequent Flyer seat is the same as if you were buying it flat-out: do an Internet search for tickets. Check fare aggregators like Kayak, Farechase, Mobissimo, whatever you prefer. (For a great review of the usability of these sites, click here). Find all the flights that are within your airlines’ Frequent Flyers partner program. Print them out. Keep them on hand.

3) Now pick up the phone. According to Better Living Through Miles, “When you do a free-ticket search on the web, most airline websites will only search their own, most-direct flights, and not their partners’ inventory or quirkier connections. If you use the phone, the agent can manually search a number of alternatives, such as partner airlines, alternate connecting cities, “open jaw” itineraries, and flights with free stopovers.”

While you’ll have to pay an extra $10 or $15 for the service of talking to a human, an agent will be able to search a larger variety of connection options for you than a website can. You remember that list of possible flights you printed out? If the agent comes up with nothing, don’t be afraid to rattle off flight numbers… Better Living Through Miles knows from personal experiences that some agents slack, and can be jarred by a knowledgeable consumer.

If you can’t get a ticket even 331 days out, you’ve got three options left.

4) Book any free ticket you can get, then reschedule. It’s that simple. You may have to pay a $50 or $100 rescheduling free but if you’re scheduling an expensive trip, that’s as close to free as you can get.

5) The four week rule. Was Number Four too risky for you? The Frequent Flyer Junta have another rule, in secondary importance: four weeks before your flight is a good time to try to book a free ticket. Cancellations and reschedules happen. Furthermore, airlines usually open up their inventory as flight date approaches.

6) Just show up. This is another variation on Number Four, but if you book any old free ticket to the cities you want to travel to, then show up on the day of the flight and ask to be put on the plane. Again, you’ll be $50 or $100 shorter, but it worked for John Ewolt of the Star-Tribune.

And that’s all the advice we can give. Like most of life, it’s largely a crap shoot… the trick is in knowing when to roll.

(Much, much thanks to Better Living Through Miles, whom is knowledgeable about the ins-and-outs of the consumer end of the airline industry almost to the point of sickness. He is an absurdly helpful and informative cat, and we can’t thank him enough for his help. Read his blog, click on his Google Ads, buy him dinner!)

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