A comprehensive guide to skiplagging — a travel hack that isn't for the faint of heart

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One afternoon a few summers back, I sat on a friend’s couch in New Orleans feverishly searching Kayak for flights back home to New York. I was on vacation but had landed an important job interview and had to return sooner than anticipated — in two days — which meant absurdly pricey last-minute fares. That was the day I learned how to skiplag.

Skiplagging — or “hidden-city ticketing” — is a flying hack where you book a flight and get off at the layover instead of the final destination because the layover city is the one you actually need to go to. It works when the fare directly to the city you want to fly to is too expensive, but connecting through that city is not. Make sense?

For example, when I needed to rush home to New York, the cheapest one-way flight cost $370. But lots of flights connect through New York (it’s a popular airline hub, which is key to skiplagging). So I searched flights to other cities in the northeast that would likely pass through New York and found a $99 flight to Boston with a connection at LaGuardia. And boom — I got off at LaGuardia, never got on that connecting flight to Beantown, and went on living my best life, $270 richer. Oh, and I got the job.

Skiplagging is a controversial hack, and it violates most airlines’ rules. "Rules," however, are different than the actual law (more on this below), and it is legal. But if you ever find yourself needing a cheap flight to a hub city, here are five things you should know in order to work the system like a frugal boss.

Travel light.

Don't check your bags if you want to skiplag. You’ll be getting off halfway there and you don’t want your bags going to another city. Also, make sure your carry-on is minimal because if the flight attendant says the overhead bins are full and decides to check your bag(s), you’re toast.

Use a general travel site to search for flights instead of your preferred airline.

The search results from an aggregation sites such as Kayak or Expedia, versus an airline’s will ensure you more options. If you want to fly on the super cheap, they’ll pull up budget airline options as well.

Don’t skiplag too often, especially on the same airline.

While skiplagging is not illegal, there have been cases where the airline caught on and threatened repercussions such as fines. So use the technique only when necessary. Honestly, airlines have bigger fish to fry than you playing hooky on a flight but don’t try your luck by doing it several times in a row with the same company.

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"Rarely do they go after people in court but it has happened, and the courts so far have sided in favor of the passenger," says Tracy Stewart, content editor of Airfarewatchdog.com — a travel deals site that doesn't, for the record, endorse skiplagging.

This should be obvious, but definitely don’t let it slip to any of the airline personnel. It's hard to get caught skiplagging if you don't do it often, but if that does happen the airline can punish you. "Needless to say, the airlines are not thrilled about all the attention to this flaw in their hub and spoke system," Stewart says. "If caught, the airline might boot you out of their frequent flyer programs and revoke your points."

Prepare for mishaps.

"Flights do sometimes get rerouted at the very last minute. In the event of bad weather or equipment issues, a flight could be suddenly be changed to connect in a new city, leaving you in a real pickle," Stewart says. "And don't expect much sympathy from the airline."

At the end of the day, my fellow travel fiends, many outlets will urge you not to break the rules. But if you’re going to do it anyway, we’re here to make sure you’re doing it as safely as possible. Good luck and keep your game face on.