Here’s What To Do When You Spot an Insanely Cheap Flight Deal

I don’t know about you, but my heart starts racing when I see a mistake fare or an unusually cheap international flight deal. I don’t gamble, but I would venture to say that the “rush” is the same when booking a flight that is selling out very FAST.



Sample flight from New York to Singapore at $328 – Round Trip


Yesterday, I shared on the Miles To The Max Facebook page, a flight deal from many major US cities to Singapore on  Japan Airlines. Staring at $319 ROUND TRIP, this was a smoking deal.

It is still a bit unclear if this was a 100% mistake fare (signs point to yes), but either way we are ticketed and confirmed. I picked up two round trip tickets, LAX to SIN, for $324 a piece! Oh yea, Japan Airlines is one of the top-rated airlines in the world.



The most important thing to remember is that time is not on your side. When you spot an insane fare, you have to consider booking within minutes. I know it isn’t fun and can even feel irresponsible, but it’s usually necessary.

On error fares/mistake fares, the airline or OTA (online ticketing agency, like Priceline), will eventually correct the issue. Once they do correct the issue, the deal is GONE. It could take them minutes, hours, or days, but don’t wait to find out.

On conventional deals that are heavily discounted, the airline will only release a select number of discounted seats. If you want desirable dates, you must book ASAP.

If you do book a mistake fare, do not make other “strict” reservations UNTIL you are ticketed and confirmed. There is always a slight chance they could cancel the flight before you are ticketed and confirmed. (it is uncommon, but within their legal right, so wait about one week)


Oh, crap

Don’t forget to select the correct number of passengers when pricing out your itinerary. I can’t tell you how many times I’ve found a flight deal, then noticed the fare jump as soon as I added a second passenger. Again, airlines only discount so many seats per flight, to get an exact price quote, choose the correct number of “adults” before you begin your hunt. (it will save you a lot of disappointment)

Per the FAA, all flights marketed to passengers in the US must offer a 24 risk-free cancellation policy. The 24 hour clock starts after booking. The only exclusion is for flights booked less than 7 days before departure. For all other flights, make sure to take advantage of this 24 hour risk free cancellation policy. Try to think of it as a free 24 hour HOLD, because that is essentially what it is. Make sure to use a credit card like the Amex PRG or Chase Sapphire card which earn additional points on travel charges.

If you see a smoking flight deal, get your credit card out and pull the trigger. You can even book multiple flights on varying dates and then cancel the ones that you no longer want. I recommend booking through Priceline as they have a quick and easy 24 hour cancellation policy. In some instances, you can book on a Friday and cancel risk-free through the weekend.


I never see any flight deals from my city!

This is one I hear all the time, and for good reason. So many medium to smaller cities will not see these insane flight deals. Many times the best international flight deals are from gateway cities; San Francisco, Los Angeles, Chicago, and New York City, etc.

You need to consider positioning flights if you don’t live near a gateway city. A positioning flight is one that is booked separately and whose sole purpose is to get you to your actual origination city. (like Los Angeles)

For example, there are $35 one-way flights between Reno, Nevada and Los Angeles. The likelihood of you finding a sub $500 R/T flight from Reno to Asia is extremely slim. With this recent flight deal from Los Angeles to Singapore for $325 R/T, it would have made sense to position from Reno to L.A.


Cheap one-way positioning flights – Reno to Southern California


Book two flights to save money?

If you spent $100 to position to L.A. and back to Reno, your total would still only be $425~ from “Reno to Singapore”. Plus, you could spend a few days in Los Angeles before departing, all for $425. If you want to hold-out for a conventional flight deal from Reno to Singapore for under $400, good luck, just don’t hold your breath.

If you live in a non-gateway city, I advise keeping an eye-out for good positioning flights proactively. I live in Phoenix, and I know that I can get to Denver, Minneapolis and Chicago for extremely cheap at the moment. If I see a smoking deal from any of these cities, I’ll give it a second glance. I like to use Google Flights’ map tool to spot cheap flights to random large cities in the US.

If you can earn Southwest Companion Pass it will make positioning even easier. For our $324 flights from LAX to SIN, we will spend a total of 7,500 Southwest points to position BOTH of us back-and-forth from Phoenix to L.A.


Flex it, baby

Rigid travel plans almost always cost more. Rule #1 of cheap travel, remain flexible. If you and two buddies have plans to travel from Dallas to Tokyo in August, you are not going to find the best deal on airfare. There is nothing wrong with picking your date and destination in advance, just don’t expect any kind of crazy deal.

— Price, Destination, Date, You get to PICK TWO!

Seriously though, these insane flight deals work best when you don’t have rigid plans. Now, if you and two other buddies said, “let’s go from Dallas to Asia at the end of Summer”, that is possible. I could all but guarantee that some flight deal from Dallas or a nearby gateway city will show up to Asia.

I have people write me and ask something like, “Caleb, have you seen any flight deals from San Jose to Austin around the 4th of July.”

My answer is typically, “Sadly, flight deals typically don’t exist when you have your start point, end point, and dates picked out already.” (and a holiday, OMG!) That isn’t to say that I won’t help people the cheapest flights available at the moment, but that is not how flight “deals” work. I still recommend using positioning flights in these circumstances, such as flying SJC to LGB on JetBlue, then heading to Austin from L.A.


That’s the way the cookie crumbles

I liken it to walking into an electronics store and asking what deal they have on a Dell 7000 series laptop with an Intel i5 and dedicated graphics. Very specific, right? The odds that your specific laptop is insanely marked-down is slim-to-none.

On the flip side, if you walked into the same store and asked, “what is the cheapest 15.6″ laptop with a dedicated graphics chip?” Well, now you have some options.

Again, I am not saying it is bad to want exactly what you want, I am just saying not to expect the best deals in those circumstances. The best deals on airfare come to those who are flexible, fast, and know how to maximize the booking rules in their favor.


Action Plan!

Step #1: Follow Miles To The Max on Facebook and choose to see notifications first (I rarely boost or sponsor my posts since I run a non-revenue blog)


Settings to receive notifications in REAL TIME


Step #2: Make sure to have you and your travel buddy’s info ready to go. (Texting and waiting for a DOB or middle name spelling can cause you to miss a deal, and yes, it must be EXACT)

Step #3: Have your credit card with you or stored in your browser’s auto-fill data. If you are away from your wallet, this could be bad if you need to lock-in an insane flight deal.

Step #4: Book a couple of flight dates if your credit limit will allow. Take the evening to figure out if any dates will work and cancel the others.



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