Courtesy of Scott Keyes
Keyes has become so gifted at landing supercheap tickets and getting the most out of his frequent-flier miles that he has booked an epic world trip that spans 13 countries, 20,000 miles, and 21 flights — all free.
He told Business Insider his process was a “labor of love” and that he enjoyed finding people the best deals he could. He created an email list to send friends updates on any amazing travel deals he finds while browsing Twitter or his RSS feed. When I spoke with Keyes, he even started giving me tips on how to find the most affordable ticket to a friend’s coming wedding in Scotland.
It’s safe to say he really loves this stuff.
And after spending five years dedicated to finding airline deals, Keyes now knows the best websites, tips, and hacks for getting tickets for dirt cheap prices.
Instead of heading to Priceline or Kayak the next time you’re planning a trip, try these three sites first:
“If I could recommend one website for people who want to get good deals for their flights, it’s TheFlightDeal.com,” Keyes told us.
Whether on Twitter or Facebook, through the newsletter, or on the site itself, TheFlightDeal.com posts what Keyes calls “fat-finger discounts,” or mistake fares that last for only a short time before airlines fix them.
“When there’s a really cheap price, you need to be able to jump on it in a couple of hours,” Keyes told us. “When I took a $67 flight to Milan, it only lasted a couple of hours because they didn’t mean to be selling them that way, we just lucked out that those were available and we were able to jump in before they fixed it.”
Ultimately, the key to finding affordable airfare is flexibility. According to Keyes, if you see a cheap flight that takes you somewhere even remotely interesting (or close to somewhere interesting), buy it and figure out the rest later.
“The way most people approach airfare, they do it backwards: They decide where they want to go and then try to find the cheapest flight to get there,” Keyes told us. “But if your ultimate goal is to be able to find as cheap a flight as possible and go somewhere cool for not much money, then starting with an open, blank slate and going wherever there’s a cheap flight right now is going to be your best bet.”
Skiplagged is a search engine that will find you the cheapest flight to your city, including “throwaway tickets.”
Throwaway tickets are flights you purchase to an unpopular destination. Let’s say you’re traveling from New York to Chicago — those tickets are going to be relatively expensive. But New York to Milwaukee will be less expensive because fewer people will be traveling there.
A throwaway ticket would be if you found a flight to Milwaukee with a layover in Chicago. Then instead of getting on the plane to go to Milwaukee, you would throw away that leg of the ticket and exit the Chicago airport.
“The only thing that people need to know about Skiplagged is just making sure they understand how to approach it,” Keyes said. “Never buy a round-trip, because once you skip a leg of your trip the rest of your itinerary cancels. You also can’t check any bags since they’ll arrive at the throwaway city and not your actual destination.”
With that in mind, Skiplagged can find you some much cheaper airfare, especially if the city you’re visiting is a major thoroughfare such as New York, Chicago, or London.
It’s worth mentioning that you can’t buy the tickets through Skiplagged. The website is currently being sued by both United and Orbitz, and now links out to a third-party website where you can purchase the deal.
ITA Matrix is a no-frills way to find the cheapest-possible flight thanks to its handy calendar index, which allows users to see the best possible itinerary.
All you have to do is search your destination and preferred length of stay and click on “See calendar of lowest fares.” The flexible search option lets travelers see what flying on each day of the week would cost them.
“Say you just want to go home for a long weekend and your ideal plan is Thursday to Sunday,” Keyes told Business Insider. “Even just shifting that by a day can be really, really helpful. If you can go Wednesday to Saturday instead — or even sometimes Friday to Monday — you can get really big savings.”
Keyes said tweaking a trip even slightly could make a huge difference. When one of his friends told him he planned to buy a $500 ticket to Las Vegas, Keyes was able to cut that price by over half simply by looking for a redeye that left Monday morning instead of the one Sunday night that his friend had originally chosen.
Kayak also allows users to search an entire month’s worth of fares, but ITA Matrix, Keyes insisted, is still the best.
One of the ways Keyes is able to fly for next to nothing is thanks to all the frequent-flier miles he has accrued over the years through credit cards, airline perks, and lots and lots of travel.
But those miles are spread out over many different cards as well as airlines. To manage them all, he uses AwardWallet, which tracks frequent-flier miles, hotel points, and credit-card points.
“Not only does it keep you organized — it keeps track of all of your accounts and points — but it also will check all your balances so you know how many points you have in each,” Keyes said. “Plus, it will track if and when your points are set to expire.”
You’ll never need to try 50 passwords to access your frequent-flier miles ever again.
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