The 10 Most Insane Travel Deals You Probably Missed

The Trip Sherpa recently wrote about DealRay, an incredibly useful mobile-based service for staying on top of travel deals, and it got me thinking of the great mistakes fares of yesteryear. I’ve been playing this game for a decade now and we have perennially seen incredible fare mistakes. Many I have capitalized on, some I have missed. Here’s a look at my personal top ten.

#10 Seattle to Newark via San Francisco, Kona, Los Angeles, Washington, São Paulo, and Chicago for $233

While not as monumental as many of the mistake fares below, I had so much fun on this trip. United forgot to impose routing rules and for a brief window you could get just about routing to book on united.com using a multi-city search–I flew from Seattle to Newark via San Francisco, Kona, Los Angeles, Washington, São Paulo, and Chicago and it only cost me $233. I netted nearly 20K elite miles and 40K award miles and even got a free hotel night out of it when my Washington – São Paulo flight went mechanical.

#9 Free Trips to Las Vegas and New York via Expedia

Expedia’s Canadian website foolishly offered $300 off any hotel + air booking to a handful of destinations without stipulations. Wise users took advantage to book cheap travel, primarily to Las Vegas and New York.

I booked several trips while the deal was still alive and helped friends and family book too — Scott Mayerowtiz, then of ABC News, even wrote about it:

Matthew Klint might have just landed one of the best travel deals ever.

Next month, Klint, his brother and his uncle are all flying to Las Vegas and staying in two rooms at a five-star hotel. The total cost: $44. Throw in a $200 food and drink credit and they are actually making $156 off the trip.

How did Klint score such a deal? The 24-year-old Philadelphia law student saw a promotion — possibly an error — on Expedia’s Canadian website and snagged it quickly…

Besides his one-night Vegas trip, Klint is taking two mileage runs from his parents’ house in Los Angeles to New York, just to get the frequent flier miles needed to re-qualify for elite status next year. The cost: completely free.

“This deal was so lucrative. There was no minimum stay,” he said. “It just seems that Expedia dropped the ball and should have put a minimum night requirement.”

Expedia declined several requests for an interview and only would say that it is honoring all bookings.

Then he started booking other trips for friends and family. Ultimately, Klint purchased 15 tickets, most of them for free.

“I always recommend to people: book now and ask questions later,” said Klint, who also has a blog about flying called Live and Let’s Fly.

A few hours after Klint booked the tickets, Expedia caught the error and changed its promotion requiring all trips to start in Canada.

This was more four years ago, but I can clearly remember these trips — mileage running to New York, fleabag hotel for the night, and back the next day. For the Vegas trips, there was no fleabag hotel — I stayed at the Wynn and with the $200 food/drink credit made money off the deal and enjoyed a spectacular dinner at the Wynn Buffet. 

#8 Washington to Beijing for $436 r/t in Business Class

I stumbled upon this deal while traveling 30,000 feet over the ground between New York and LA — thank goodness the flight had Wi-Fi. I had never flown AA First Class and used a SWU to upgrade the Chicago to Beijing leg. While AA’s very outdated first and business class on the 777-200 was a disappointment, the miles alone made it worthwhile and premium cabin mileage running never grows dull. 

#7 Air Canada Chicago to Mexico City fares

This was my the first mistake I actually took advantage of — way back in December 2007: ORD-YVR-YYZ-EZE-GRU-MEX in business class for $514.

• Chicago to Vancouver on United
• Vancouver to Toronto on Air Canada
• Toronto to Buenos Aires on Air Canada
• Buenos Aires to Sao Paulo on British Airways
• Sao Paulo to Mexico City on Aeromexcio

I booked this in December for travel at the end of February. The reservation stayed ticketed and confirmed until early February when Air Canada unilaterally cancelled my ticket then called my house to let me know what they had done. By then, I had already booked positioning flights (to Chicago, from Mexico City) and as a young and rambunctious aspiring law school student, I decided to fight it…and settled with Air Canada in an agreement still under a non-disclosure agreement. Trust me — it was worth it.

#6 Three Rounds of Cheap Burma Fares

Whatever the cause of this thrice-recurring error fare, I invested hours into constructing elaborate routes to travel from Rangoon, Burma back to North America in the comfort of business and first class. I first wrote about it here and ended up booking three tickets–one on Delta for about $400, one one Singapore Airlines for about $550, and later (during “Round 3”) a first class ticket on Swiss Air for about $1800 that included Singapore Suites and points-elusive Swiss First Class.

Swiss cancelled that fare and I opted not to fight it — some spent months working with the U.S. Department of Transportation and Canadian Transportation Agency to get their fares honored and still failed. Delta and Singapore did honor the business class fares I booked, though I ended up cancelling the Singapore Airlines fare. My Delta ticket included business class from Rangoon to London via Bangkok on Thai and then Delta to New York — not bad for $400 and change.

#5 United Business Class to Auckland via Sydney for $1100+tax

As I recently said on Fox News, “He who hesitates, loses.” I remember sitting in my office, 19 years old, when I noticed this fare on Flyertalk. Business Class on United to Sydney, then a connection to Auckland on Emirates, Qantas, or Air New Zealand. So excited, I consulted my calendar, called up my brother, called up my uncle, agreed upon travel dates, then went into book…all looked good! I could not decide which carrier I wanted to fly Sydney to Auckland…I started googling reviews of each carrier’s business class and though it only took five minutes, by the time I went into book the fare had been pulled and I missed out. So much for a fully-refundable business class that was easily also upgradable to first class. I still kick myself for missing out on this one!

#4 Colombo, Sri Lanka to Dallas in Etihad First for $1450 r/t

It could not have worked out more perfectly — first class from Colombo to Dallas on Etihad on exactly the dates I needed for my honeymoon: we were going to the Maldives! Ticketed and confirmed, Etihad said it would honor the fare and I gleefully announced to my wife where we were heading for our Flitterwochen. She wanted to go horseback riding in the German countryside instead… That’s okay, these tickets were fully refundable. We actually ended up going to Paris, but we will finally get a chance to travel to the Maldives again this winter. This time, sadly, not for $1450, but 180K AA miles each…

#3 Hilton Moorea Lagoon Resort $120 Overwater Bungalow with Meals Included

Tahiti is not usually the place to go with your uncle or brother, but my uncle has always wanted to go and when Hilton goofed up a currency conversion, overwater bungalows with breakfast and dinner included were available for $120/night. 

I booked five nights and after some back and forth the hotel did agree to honor the rate. I had to cancel this trip too, unfortunately — we were too cheap to buy tickets from Auckland to Tahiti and back — but this was truly a once-in-a-lifetime deal for this amazing property.

#2 Swiss Business to New Delhi for only the Taxes

I am a fighter, to my credit or detriment, and also had a strong desire to visit India. When Swiss filed a $0 business class fare from Toronto to Delhi in late December 2008, I jumped on it and with the help of the Canadian Transportation Agency and a refusal to backdown to Swiss’s lawyers, the fare was eventually honored and my brother and I traveled to India in style — though not without some drama. You can read my pre-blog Flyertalk trip report here. With taxes, the round-trip business class ticket to India came out less than $500.

The Washington Times even picked up on the story–

…Some passengers, however, rejected Swiss’ decision and, armed with e-mail confirmation of their purchases, got ready for a fight. Arguing that the airline should bear the consequences of its mistake, some even threatened litigation.

“I entered into a binding contract for air transportation,” Matthew Klint wrote in a letter to Travelocity, on whose Canadian site he’d bought a ticket to New Delhi. “Swiss’ and Travelocity’s efforts to modify, vary or call into question the terms of the contract more than two days after its execution is not acceptable and will be considered a material breach of contract.”

Mr. Klint’s repeated attempts to reason with representatives of both companies proved futile. Travelocity blamed Swiss, saying that “because 78 reservations were made, it would not be willing to pay for a mistake that Swiss made,” he said. But Swiss sent him back to Travelocity, because, “as a travel agency, it’s ultimately responsible for honoring a fare that they confirmed.”

Finally, Mr. Klint’s luck changed when he contacted the Canadian Transportation Agency, which asked Swiss to resolve the issue.

The airline relented, agreeing to fly Mr. Klint in business class from Los Angeles to Zurich and on to New Delhi at no extra cost. The new routing meant it didn’t have to pay Air Canada for flights between Toronto and Montreal in the original itinerary, and it worked out well for Mr. Klint, who lives in Los Angeles and had booked a separate “positioning” flight to Toronto.

“All four flights were wonderful,” he said after he returned home last week. “Swiss’ trilingual cabin teams are superb, and I enjoyed every minute of the roughly 38 hours of flying time.”…

#1 Alitalia $33+tax business class fare to Larnaca, Cyprus

This was the first error-fare I was ever stumbled upon (I did not book) and I think it is also the most entertaining mistake fare of all time. The deal was Toronto to Larnaca in Alitalia business class, but generous routings were permitted and unlimited stopovers were also permitted. Thus, stops in several U.S. and European cities were possible. Alitalia first cancelled the tickets, then caved in and reinstated the tickets, even allowing changes and the addition of stopovers. Bellissimo!

All of these deals above I could have jumped on, but only because I was teenager or in my early 20s hovering over Flyertalk like a hen over her eggs. That’s not possible any more — most of us have better ways to spend our time, as fun as checking the “Mileage Run Deals” forum on FlyerTalk 180 times a day is.

That truly is the beauty of DealRay. You don’t have to worry because DealRay is tracking space for you — and when that great deal pops up, you’ll simply receive a text message and if the deal looks good, you can rush in to try to book it.

Remember that DealRay is not not just about “mistake” fares, but about great deals too. You can check out some past DealRay notifcations here. For $9.99/month this service is totally worth it — even if you only take advantage of one deal every couple years, that money you save on a mistake fare or a great sale more than pays for the memberships. I consider it a small insurance policy.

Due to the robust response from Kyle’s post, DealRay is extending its special offer UGPRD readers through August 17, 2015. Sign-up here and you’ll start with two-months free. 

If monitoring FlyerTalk is still your thing great, but by the time I post about a great deal, it will only be after I have booked all the tickets I need and that means you won’t read about any great deal on this blog as soon as it breaks. That seems to be the MO among others as well. Take advantage of DealRay and never miss a great fare.

What are your favorite mistake fares? Did I miss any?

^{Pictures from Wikimedia Commons / Post sponsored by DealRay}

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