How Do We Get Cheap Flights?

There is no one answer or simple set of steps to get good flights. It takes a lot of research and luck to get the best deal available.

If you have a problem with words, skip to the bottom for the dirty details and links.

How much is your time worth?

There are so many articles, tricks, sites and hacks out there to try and secure the best deal. It all really comes down to how much your time is worth. You can spend hours scouring and trying all the tricks in the book to get a good price. In reality, it comes down to the time you put in and timing. There’s no one special sauce that will work every time. But a few solid techniques can help you speed up your searching and at the end of the day if you like the deal, book it!


Timing is a huge factor

I’m not talking about the “book on a Tuesday” rule but different airlines will offer rates on their own timeline and platform. Sometimes you may come across a last minute deal but generally booking early is best, at least 2-3 months ahead of time. Timing is also affected by how flexible you are.


Be Flexible

For ridiculously cheap fares you not only have to be flexible with your dates but also your locations. Sites like the Flight Deal or Scott’s Cheap Flights, publish crazy low rates from US cities constantly. The trick is actually being able to book a $137 round trip flight from New York to Milan when your brother calls you at 2am about the deal and you say yes without looking at your calendar.

Also it helps to be flexible +/- as many days as you can. Flying a day or weeks later can save a bundle. Also consider nearby airports at you point of departure as well as arrival for better deals.


Location, Location, Location

It helps to be near major airports and hubs. If you live near a small airport, don’t be surprised if there aren’t many cheap flight deals. It’s simply a matter of supply and demand. By living in the northeast, we are able to choose from a bunch of different airports. But your hub will also determine what locations are cheap. It’s much cheaper to get to South America from Atlanta and Miami or from New York to Europe. It’s a matter of the number of routes connecting these cities that force airlines to compete.


Use a VPN

Where you book from can have an immense impact on your final price. Some people say that even booking on a Mac vs PC will result in higher prices. We haven’t seen or tested this exact theory but we have noticed that where you book from has a massive impact on your price. For example a flight from Lima to Boston was over $200 cheaper by merely changing your booking location from the USA/English site to the Peru/English site. A VPN will help you match your location to the country you’re pretending to book from, just make sure you manually select a server in the country you want to book from.


Loyalty is for Losers

It never really works out to try and book only on one airline to earn more points with them.

Spending extra real dollars to earn more points will never net out unless you make a career about tracking your points and doing things like manufactured spend. Unless you fly a lot on someone else’s dime on one carrier family, always choose the cheapest flight. The exception to this rule is if the flight is on United or Spirit cause, ew, gross. With that said, you should still collect points when you can. Sign up for all the loyalty programs and try and consolidate with one airline. Most major carriers let you earn points on partner airlines but like I said earlier, keeping track of it all can be a full time job.

TLDR – The Quick Info and Links

The sites we use to search for flights:

The Flight Matrix

This one takes a bit of training and getting used to but it is probably the most powerful flight search tool available and of course Google now owns it.



Originally I thought Skyscanner was just another Kayak but they consistently have some of the best rates available. We mostly use it for their ability to show flights from my city to “Everywhere”. This gives you a list of flights anywhere in the world ordered by price. Who knew you could get to Manchester from Newburgh, NY for under $300.



When a flight search startup gets sued by an airline you know they’re probably doing something right. Skiplagged searches for flights with stops in the places you want to go. For example if you’re trying to get from New York to Miami. It will find you a flight from New York to Dallas that’s cheaper but has a stop in Miami. All you have to do is book the JFK»DFW flight and get off in Miami. Fair warning though, this only works on one way flights and obviously you can’t check a bag. Airlines also get really angry when you do this and might cancel your earned miles account in retaliation. But refer the note above about loyalty and losers. In addition to travel hacking, Skiplagged does a good job of scouring for other normal flight deals as well but isn’t comprehensive.


The Sites We Use For Booking


Orbitz is not a great tool for searching but a great tool for booking. They let you cancel within 24 hours an almost all flights, no questions asked. This is ideal for locking in a fare but still having 24 hours to due diligence search for a better deal and make sure you got the best price at the time.


Chase Ultimate Rewards

The Chase Sapphire family of cards is one of the best ways to earn points and redeem for travel. It is consistently highly rated by travel hackers and point people. The only thing Ultimate rewards is good for is redeeming for flights or cash. With the Reserve card you get a 50% point multiplier when you book a flight so your $500 flight will only cost you 33,333 points or $333 cash equivalent.


Go Direct

A lot of airlines either don’t publish on aggregators or publish deals on their own sites. It helps to search directly on airlines like Southwest, Jetblue, Emirates and a few other. If you find a great deal somewhere else, sometimes the airline might have a promo. Even if the ticket is the same price, it’s better to book directly to get a better fare class for point earning, if you’re into that sort of thing.


The Forever Search

This is all I can think of for now. At the end of the day, we try to find deals quickly for what suits our needs. Sometimes we have a specific place in mind we’d like to go and realize we have to pay a premium for the preference. There have been times that we have spent way too long and wasted precious time searching too much instead of booking and getting back to paid work and actually taking a break sometimes.


If you have any tips you’d like to share or any glaring omissions we’d like to hear about it!

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