How to Book the Cheapest Flight like an Expert

My own personal cheapness and desire to travel has made me go to extreme lengths to find the best methods of booking a flight while spending the least. This is a list of every tip and trick I know, from the obvious (#1) to the ridiculously time-consuming (#23). Go down the list and see if you can find a new way to save money like a pro. For your convenience, I have also listed drawbacks if any.

Peach Airlines

1) Flight Search Engines

The most common way to save money is to not be attached or loyal to any single airline. Flight search engines like Kayak, Orbitz, Expedia, Momondo, Vayama, Edreams, Cheapoair, and BYOJet can be used to find the cheapest possible flight by cross-referencing many airlines. To elaborate on the notable ones:

  • Kayak – Its simplicity and ease to use makes it my top choice bar none (and no I wasn’t paid to say that). It also has an interesting feature called “Kayak Explore” that lets you search by price instead of destination.
  • Sky Scanner – Another great search engine. Its best feature is the ability to be able to search from one destination to “everywhere” giving you destinations by price similar to Kayak. Note: I have on occasion found its ‘cheapest flight’ to be mysteriously ‘sold out’ so use with caution.
  • Priceline – Has the ability to negotiate deals on flights and even upgrades.


2) ITA Software Matrix

This Google engine is amazing in theory, but falls short of being your “go to.” In theory, it should be able to search every possible flight, including local airlines often missed by flight search engines. The pro is that it gives you an insane amount of options to tinker with and an unbiased route code which you could then give a travel agent to book the cheapest flight OR book it yourself on a different engine (ITA does NOT sell flights). One con I have found is that it sometimes gives you results for sold out flights. Nevertheless, it’s definitely worth checking out.


3) Travel Agents

If you’re not a newbie, you probably have learned to avoid travel agents. While this is sometimes wise, it is not always more expensive outside of the US. I never fly out of Korea without checking what rate a travel agent can give me. They often reserve flights in bulk early on and sell them at a profit, but cheaper than the current going price (especially on short notice).  This is true in most of Asia and while I have not tried it myself, some of my friends vouch for the cheap rates their agents get them in the US as well. My agent of choice is  Soho Holiday (out of Korea).


4) Churning

If you have never heard of churning, you owe it to yourself to stop reading this article RIGHT NOW and read this one first. In short, churning is a method of gaming the Travel Credit Card industry by cashing out on their ‘bonus miles at signing’ and using it for nearly free flights.


5) Groupon

Groupon, along with many similar sites often have great deals on flights. Your choices may be limited, but hey, a cheap getaway is sometimes all you need. Furthermore, other countries have these too, notably Korea’s Coupang and T-mon. I personally used Coupang to find the cheapest flight from Seoul to Okinawa. I paid $200 round trip, nearly half of what Kayak was quoting me.

Wings Airlines

6) Budget Airlines

As much as search engines try to convince you, they definitely do NOT cover all budget airlines. There are two to consider:

  • Budget Airline Giants – Ryan Air in Europe, Air Asia around Asia (centered in Kuala Lumpur), and Nok Air in and around Thailand are just three budget airline giants that specialize only in budget flights. Many like Allegiant Air and Spirit specialize in and around the US too. This is especially useful if you are the type who travels very light as they separate the cost of luggage.
  • Small Budget Airlines – Given the 8 figure prices on airplanes, some airlines simply cannot afford to spread too quickly. Many own just a handful of airplanes and go to a handful of destinations, but this could mean big savings for you. Use methods #12 and #23 to find out where they are and where they operate. It should be noted that many countries have domestic only airlines which never appear in international search engines.


7) Total Cost of Baggage / Fees

Budget airlines often sound WAY cheaper than the alternative. While they do save money, they are riddled with hidden fees that can kill you if you’re not careful. Baggage is the main one. Jetstar and Air Asia are notorious for charging as much as $15 PER KILO if you do not pre-purchase baggage. Other ridiculous fees include Air Asia’s ‘fee for paying with credit card’ or ‘fee for choosing to sit together’ which has never been a problem to get for free at the counter upon check-in (so don’t be fooled into thinking you have to pay for this). Budget airlines usually do not offer anything to eat on flights, including long-haul ones either. They are still worth it, but be careful, know what you’re getting yourself into, and do the math accordingly.


8) Total Cost of Your Time

This may seem a little much, but one thing I consider during long layovers is the cost-benefit of how long I travel. You see, the more I am in transit, the more antsy I get and the more food I start buying (and maybe even a coffee or beer). If a flight is $20 cheaper, but has me on a 15 hr layover in a city I have no interest in exploring, I am going to eat and drink my way through $20 pretty easily. Again, do the math.

Note – This was worded in this way because of #13


9) Alternative Airports

What’s is the point of saving a couple of bucks if you’re going to spend it on the bus to town? Many major cities have multiple airports, and sometimes, it is cost effective to spend a little more to be much closer to the city center. One that comes to mind is Osaka International Airport, not to be confused with the larger Kansai International Airport. While the latter is more popular, the former is considerably closer not just to Osaka, but to Kyoto and Kobe, which could save you time and money. Others I have encountered are Los Angeles (5 airports), Tokyo, Seoul, New York, and Milan.


10) Skiplagged

A website that has been buzzing around the water cooler these days is Skiplagged. On occasion, it is cheaper to fly, for example, from LA to New York than from LA to Dallas. However, what if the LA to New York flight had a layover in Dallas? Skiplagged searches these loopholes for people with the intention of getting off at the layover, hoping to get a better airfare. This has been so irritating to airlines that they have tried to sue the creator (unsuccessfully) a couple of times. It is a nice option, but you should be aware of four drawbacks.

  • First, airlines don’t like it and if you do this constantly, you could be red-flagged.
  • Second, on occasion, airlines do force you to check in your carry-on for ‘security’ purposes (has happened to me from Mexico to the US). If you intended to get off in Dallas, you’re shit out of luck as your baggage is going to go all the way to New York!
  • Third, if you bought a return flight and purposefully skipped the connection, your entire itinerary will be cancelled, including the return flight. This only works on one way flights.
  • Finally, you can’t skip the first leg of your trip intending to catch the second one. That is to say, if you found a cheap flight LA>Dallas>New York and intended to only board in Dallas, it is not possible. The whole itinerary will be cancelled as soon as you miss the first leg.

These criticisms have been brought to you by my sponsors, American Airlines! Just kidding… (shifty eyes)


11) Foreign Search Engines

I am not sure how many exist, but one I recommend within China is cTrip. This engine consistently gives cheaper flights in the People’s Republic, and they now have it in English too! In addition, cTrip often has booths in main airport hubs in case something goes wrong.



12) Airport Websites

Individual airport websites gives you info on what flies in and out, which is useful if using method #23. In addition, it could also give you info on leaving the airport and your options. Using Miami’s airport website, I realized renting a car out was cheaper then taking a cab to my hotel for the night. It also allowed me to explore the Everglades National Park at no additional cost as I already had the car :).


13) Forcing a Layover

Is there a country that appeals to you enough to visit if it were free, but not enough to base your whole trip on it? Consider forcing a layover in said country. Depending on the airline, you could delay connections for 10+ hours or even a few days. Mini-trips to Amsterdam, Shanghai, and Sydney all came about because of purposefully long layovers. However, a delayed flight could put this whole thing in jeopardy. I actually had planed to spend two full days in Shanghai, but like clockwork in China, the flight was 7 hrs late. For this, you also have…


14) Multi-City Flights

Have too much vacation time (boohoo, I know) and would like to split it between two nearby locations? Try this to save some serious dough. In 2012, I got a flight from Seoul to Taipei, Taipei to Macao, and Macao back to Seoul for under $500. Backtracking would have cost a ton more, not to mention the wasted time.


Looks like its Cloudy

15) Combine #1 and #3 and #4

Sometimes, the cheapest flight is not so straight forward. When Sarah came to New Zealand from the US this last fall, we booked on Kayak one-way, then within New Zealand on budget airline JetStar, and finally on American Airlines rewards to get home. It isn’t without risk, but the savings can be staggering if you get a little creative.


16) Book Two and a Half Months in Advance

This goes against ‘expert wisdom’ but I am confident that 2.5 months is the sweet spot. I understand that 6 weeks before a flight is statistically the cheapest, but there is a cost-benefit everyone seems to ignore. IF your flight gets sold out and there are no other options, you’re SCREWED. At 2.5 months, flights are usually at a really good rate and to me, paying $10-$20 more short term saves me money from having to potentially shell out hundreds more for waiting too long.


17) Be Flexible with Your Destination

To counter #16, you don’t always have to book that far in advance. If you become a consistent traveler, you will eventually go everywhere you want to go. Have a list of the places you want to visit, and try to get to them in the order of which ever flight is cheapest at the time of the usually recommended 6 weeks prior to departure. This is a long term commitment, but worth it.


18) VPN

If you have a stubborn flight that seems to be expensive no matter what, try to start up a VPN like “Hola” to change your location to another country. The Flight Search Engine will detect this and might give you a better rate. Experts say using your location as the US is best, but from personal experience, it varies.


19) Cookies

Ever get stressed out and can’t find a cheap flight? The answer is pretty simple. Research shows that grabbing a glass of milk and eating some cookies lowers the average price of flights by 10%! If you bought that, you really have been staring at your computer screen for too long.

Seriously though…

The computer term for cookies is a marker left on your browser when you visit a website. Some search engines use these ‘cookies’ recognize that you are tracking a flight and use it against you. For example, if you search for weeks “San Francisco to Dallas” it knows you HAVE TO GO, and will systematically show you a higher rate. Clear your web browser cookies and try again.


20) Get Miles from Friends

Some of your friends might have points or ‘miles’ they can’t use before the expiration date. Have them book you a flight and make a deal where you get a cheap flight and they make some cash on the side! You didn’t hear it from me, as airlines are not very fond of this practice.


21) Double Check

Don’t take a Flight Search Engine’s word for it, go to that airlines websites and make sure it is the actual rate! If it is all the same, it is usually better to book directly with the airline as they have better terms and conditions. I should note that I’ve never had issues with Kayak, but my last cancellation was years ago.


Wings Airlines

22) Charge the Local Rate

I realized this one today actually. Some websites can give you the option of charging in their local rate, or ‘converting for your convenience.’ Your convenience is also on your dollar though. Their converted rate usually banks a pretty nice profit for themselves (3-4%), so just go with the local rate as your credit card is more than likely to do for free and at the very worst, charge 3%.


23) Wikipedia

This is probably the most advanced and time consuming tactic on the list. Search: “wiki airlines in (any country).” You will find a wikipedia page with a list of every airline in said country. After that, systematically go to each of those airlines’ websites and check out their rates one by one. Many of them will be smaller or budget airlines which don’t show up on flight search engines. The catch? Not all of them will have a website and if they do, it might not be in English. Nevertheless, it might be worth the trouble.

When I personally search for flights near Korea, search engines usually skip the 7 or so budget airlines in the country. Quite inconvenient given how the domestic flight of Jeju to Seoul is the most traveled route in the world. Another example would be Myanmar. Try booking a domestic flight within that country and you get a ridiculous flight path out of the country and back into it, and only a single domestic airline flying direct, despite there being 9 other airlines in the country.


Do you have any methods I missed? You must because I get this crazy feeling I am forgetting something. Put it on the comments.

And yes, I did just put pictures of numerous planes. Sorry I wasn’t more creative 😛

Julio Moreno
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