Frequent flyer award tickets are one thing, you can get amazing value. But when airlines and hotels give away their product nearly for free, you can do even better — and usually without having to constrain yourself to dates that are available on points.

here are some of the best deals that have come along, and what to do when they appear.

There have been some amazing opportunities to fly and stay due to fat finger mistakes

There were $28 rooms at the W Times Square and $2 fares to Lebanon, New Hampshire.

Hilton used to have a booking engine glitch where a reservation made about a year out for check-in on December 31 would cause many hotels to price all room nights after that, in the next calendar year at $0. I stayed at the Hilton Barbados, in a suite at the Hilton Nassau, and made a booking I ultimately cancelled for a villa at Arizona Biltmore this way.

The Crowne Plaza Venice East had rooms for 1 euro cent. They honored it, and offered you points if you would cancel it.

I stayed in a junior suite at the Renaissance Seattle for less than $30.

Air Pacific sold Los Angeles – Fiji flights for $51 roundtrip.

In 2005 I picked up that Travelocity was pricing Tickets departing Tahiti at 10% of their normal price. It was a currency conversion issue, and the following day it was discovered that you could take advantage of this flying anywhere, in any class of service. With paper tickets many people started off with Air Tahiti Nui from Tahiti to Los Angeles, tossed the first flight coupon, and originated their trip in LA.

Airline mistake fares are far less common today than they used to be

Back in 2009, the Air Tariff Publishing Company which distributes international airfares, added an “are you sure you really want to load this fare?” screen for international fares. When fares are exceptionally low relative to existing fares in the market, they flag that for the person keying in the fare and that gives them a chance to say ‘whoops.’

And that likely goes a long way to explain why it’s so much more rare than in the past that we find mistakes that are 90% off usual price.

Most mistake airfares, now, come from:

• Misfiled routing rules. There’s not a check that I’m aware of to make sure that customers aren’t going to be able to fly an unlimited amount on a fare (that the person entering the fare forgot to include maximum permitted mileage, specific routings, or a rule to bump up the fare based on the fares from a connecting city to the destination aka a HIP check or higher intermediate point check).
• Dropping fuel surcharges off the price of the ticket. When n ticket is issued on ticket stock of a carrier that doesn’t have an interline fuel surcharge agreement with one of the airlines in the itinerary, and the tables haven’t been properly updated in IATA’s system to handle the split, the pricing engine may drop the charges when pricing the ticket. Incidentally, it was ATPCO that helped United close the loophole of adding a flight to Canada onto the end of an itinerary when Airfare Watchdog wrote about the ‘trick’ in March 2010.
• Less sophisticated airlines who don’t understand the tools they’re given and aren’t willing to seek help. That’s why we still see the occasional mistake fare originating in South or Central Asia, frequently on airlines like Thai, Air India, and Malaysia.
• Currency conversion errors, either an error in a pricing system’s logic or as a result of a currency devaluation.

The most important principles for handling mistakes

When a mistake fare does come up, don’t call the airline under any circumstances until the deal is no longer available.

And if a deal isn’t ultimately honored, don’t threaten to sue.

When a mistake comes along, don’t be greedy. Book what you’ll use. When the Tokyo Hilton had executive floor rooms bookable at $3 per night, there was someone that booked it for a year — figuring they could have breakfast near their office every day and then evening cocktails after work. Driving up the cost of honoring a deal can make it less likely that the travel provider will honor that deal.

Finally, after making your booking take a pause. Wait a couple of days to see if it’s honored. Don’t book non-refundable travel associated with your mistake immediately.

This last advice may be controversial. For air travel originating or terminating in the U.S., you can usually expect it to be honored and if it isn’t at a minimum the Department of Transportation will likely require that any non-refundable costs incurred in reliance on the fare be covered by the airline. But that process will be a hassle at best and I think it’s better to wait.

That’s true even though booking for immediate travel, before an airline can decide to cancel and notify travelers, may be one of the best ways to leverage these fares — when United didn’t honor its 4 mile awards to Hong Kong and beyond they did let travelers booked within a week travel.

Here are the very best mistakes there have been in my time in this space

Here’s my top 10:

1. Alitalia $33+tax business class fare to Larnaca, Cyprus (April 2006). The fare permitted stopovers in Italy in both directions and required departing from Toronto. The intention was to file a $3300+tax business class fare. Initially Alitalia refused to honor the fare and began cancelling itineraries. They got pushback from some Orbitz lawyers, presumably over the unilateral handling of the situation. They agreed to honor the fare, but reconstructed itineraries to remove stopovers. In some cases travel dates were changed significantly. Then they conceded that was problematic, and began restoring itineraries to their original, but in some cases there was no codeshare availability on the flights between Italy and Cyprus (which were operated by Cyprus Airways) so people were rebooked on different dates, in a different class of service, or found themselves without any flight between Italy and Cyprus at all. Or flying to Cyprus with no way back (such folks were dubbed “the swim team”). This mess was given to one amazing staffer in Alitalia’s New York office named Nicolo to fix. The deal became that these tickets were fully changeable — once. You could change your dates (time of year even). You could change your routing. Add or delete stopovers. The only requirements were that you actually had to fly to Cyprus (a handful of folks circumvented this early on dealing with Alitalia’s Canadian office) and once reissued your ticket became non-changeable.

2. Premium cabin fares originating in Yangon, Myanmar There were three rounds of this mistake. You had to originate in Burma, route however you wished and wind up in Canada. Swiss told people who booked these fars on their ticket stock that they were bad people

3. Colombo, Sri Lanka to New York JFK one-way for $1100 in business class (Fall 2007) This was a great fare, but tickets departing Colombo were often cheap. What made this an amazing mistake fare was that it lacked any routing or maximum mileage restrictions, which meant that folks could fly on a ton of different airlines, all over the world, as long as they started in Colombo and the ticket concluded in New York. Folks flew well over 20,000 miles one-way.

4. The Le Meridien $33 Khao Lak Oceanfront Villa (December, 2006). The hotel published its 3 and 4-night discount rate plan in Ugandan Schillings instead of US dollars. That made a ~ $1500 a night 3100 square foot 2-bedroom Oceanfront Resident with Private Pool 60 cents per night. The hotel determined that they wouldn’t honor the rate, but offered $50 per night (with third night free, thus effectively $33.33/night) insead. And the rate included tax and breakfast, the latter normally costing more than the room rate itself. Some lucky souls timed their Khao Lak Ugandan Schillings trips to coincide with Bangkok travels, combining a an Oceanfront Villa stay with a Conrad Bangkok Presidential Suite stay for $51 per night.

5. $3 Hilton Tokyo/Osaka (November, 2005) Expedia displayed rooms at the Tokyo and Osaka Hiltons without the last two zeros in yen, so instead of ~ $200 a night for a standard room and $300 a night for an executive rooom (complimentary breakfast, evening cocktails, internet) the rooms became $2 and $3 respectively. Expedia did cancel some bookings but honored a good many as well. This was the first hotel mistake rate I benefited from.

6. Hilton Moorea Lagoon Resort $120 Overwater Bungalow with Breakfast and Dinner (January, 2009) When Hilton took over management of three French Polynesia properties from Starwood (the former Sheraton Tahiti, Sheraton Moorea, and Bora Bora Nui) I wasn’t surprised that they had currency conversion issues. Bora Bora Nui itself had currency issues when it first went online, creating a famous mistake rahe that wasn’t honored (when the hotel sent a mass email to notify guests of its decision, they failed use the Bcc: filed and violated Starwood’s privacy policies so everyone that booked the rate received 10,000 Starpoints as an apology if I recall correctly). Hilton priced the Moorea property in Congolese Francs (CDF) instead of French Pacific Francs (CFP or XPF). That made a $1000 a night overwater bungalow a bit over $100 with meals included. Initially Hilton refused to honor, but then relented for those willing to convert their cancellable stays into prepaid stays (the prepayment naturally scaring away those not certain to use their reservations).

7. United Business Class to Auckland via Sydney for $1100+tax (Spring 2007) United loaded a C fare, which means full business class, so availability wasn’t an issue. And it was a weekend, so the fare lasted for days. It was also upgradable to first class for the US-Sydney flights, with onward travel to Auckland on other airlines.
   
8. Intercontinental Bali Imperial Villa as a reward night so just 30,000 Priority Club points. (2006) Priority Club long had an issue with hotels loading all room types available for award redemption, and this was certainly one of the very best ones in that overall mistake genre.

9. Mexicana ~ $55+tax business class fares from their US gateways to Puerta Vallarta (summer 2002). This was the very first mistake fare I jumped on.

10. British Airways $20+tax World Traveler Plus fare from several US cities to several points in Europe (fall 2002). I missed this one while I was on the beach in Puerta Vallarta.

What other mistake fares deserve to be on this list?

When you hit the comments, please be sure not just to list other mistake fares, but make the case for its inclusion — explain the value and why it merits being on the list instead of one of the items I preferred.

There are plenty that didn’t make the list, such as ones I mentioned at the top of the post and others like the $200 first class fares on US Airways to St. Croix (I used this as a jumping off point to St. Maarteen and San Juan) and the $61 Iceland fares. But this is a top ten list, after all!

---

You can join the 40,000+ people who see these deals and analysis every day — sign up to receive posts by email (just one e-mail per day) or subscribe to the RSS feed. It’s free. You can also follow me on Twitter for the latest deals. Don’t miss out!