Finding The Right Flights: Where You Should Look and When You Should Buy

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So let us guess! Your friend told you that it’s cheapest for you to buy your flight on Tuesday night or early Wednesday morning, so that you can get the best deal possible. You then followed said friends advice and found out that it just didn’t work this time, or maybe you kept changing browsers into incognito mode, only to further download a VPN and try to see if that worked…and well that landed you here! So we should thank that friend. THANKS FRIEND!

Are they wrong? Well No… Are they right? Well No…

“If you think you’re right, then you’re probably wrong!”

Booking a cheap flight 101

When it comes to booking a flight you have to remember you’re dealing with super computers that are collecting millions of pieces of data per minute and processing it through extremely difficult algorithms that take every single factor into account such as:

  • weather

  • holidays

  • events

  • season

  • seats left on the plane

Where to begin

It’s taken us years of studying trends while traveling and spending hundreds of hours trying to see what kinds of searches brought back the best results…and yes we failed many many times! We actually can’t emphasize how many times we’ve actually tried techniques we thought would work, only to find out they’re just not good. Now we are here to show you just how the techniques that really do work, operate. If we could explain it in one quote it would be from the brilliant Thomas Edison.

"I have not failedI've just found 10,000 ways that won't work."


    Mainly, we start every single search from 1 of two places, for Jim he prefers to start with Google Flights and for Inna she likes to start with Skyscanner. The difference being that in the U.S. it’s more popular to use Google flights, and Skyscanner is more favorable in Europe. But as we’re discovering Skyscanner is now putting a huge foot forward into marketing within the U.S.

  2. Being flexible with your dates

    Say you want to go to Bagan in Myanmar, but you want to find the cheapest time to head out that way. Both of these sites allow you to search for flights not only within a weeks time, but you can search by the month to find the price that is right for you. Now to take that a step further!

  3. Being flexible with your airport

    Luckily for you, both Google flights and Skyscanner offer you the option to pick the region you’re leaving from. In this instance let’s pretend we’re leaving from New York City, so instead of showing you the three options that’d come to your head (JFK, La Guardia, and Newark) it’ll show you every airport within 3 hours. So now you’re immediately flexible with your airport and your dates, so you’re one step closer to booking that flight…right?

  4. Let the detective work begin

    If you have to get to Santorini for example, don’t search NYC to Santorini – that’s just plain old stupid. Try looking NYC to Athens, then Athens to Santorini and compare to the price you saw for NYC to Santorini. Usually flights to major cities are much cheaper.

    From there you can figure out, “ok is it worth it to save such amount of money for this amount of time, or is it not” 9/10 times it will be!

  5. Off season

    Sure you want to go to Santorini when it’s perfect weather conditions, but that puts you on the list with every one in the world.  Jim went last fall spur of the moment from Athens and got to experience it for less than you could imagine. He went for a whole week and stayed in a regular hotel, a mid-range hotel, and a luxury penthouse with his own infinity pool. Normally the regular would cost $50-60, the mid range would could $100-125, and the luxury is $400+. He managed to walk around and since no one was there, they were willing to take half price for the hotels! Don’t worry you’ll still get your gorgeous shots of Santorini, regardless of if it’s high season or low season. The only difference is it’s cold and you’re not going to go swimming, unless you don’t mind the cold water of course.

  6. Best time to book

    Book tickets around 2 months before you have to leave for the best prices possible. Never buy more than 4 months in advance or within 2 weeks of your flight, as they’ve no reason to lower prices in that time frame since it’s supply and demand.

  7. Best days to fly

    Try to get flights on Tuesday, Wednesday, and Saturday. This is for the reason that less business people tend to fly on these days resulting in lower fares. Please do not get this confused with days to book, we’re actually saying that these are usually the cheapest days to physically fly.

    Pro Tip: Avoid flying for holidays, unless you’re flying ON Thanksgiving or ON Christmas day or ON New Years…these days have turned out to be the least expensive days to fly since no one wants to fly on them whatsoever. However, if you’re a person with a limited amount of time, you have to take into account that services/places may not be open due to it being off season or a holiday. For Inna and I we’ve gone to lots of places off season which have no big crowds…however, always tons of things under construction and weather may not be in your favor.

  8. Dates are set! Now what?

    So you know where you’re headed and you’ve got a rough time frame for when it is you’re going to be headed there. It’s time to take those final few steps that take a bit of time. You’re gonna find the price that’s right for you whether it comes from Google Flights or Skyscanner, and you’re gonna go directly to the airlines site in which you saw the cheapest price on one of those two search engines. We say this because sometimes they post cheaper prices or you’ve got some sort of coupon code, or loyalty points that have to be used and you can use them up. Now, sometimes it’s actually just cheaper to book through 3rd party sites that pop up through those search engines and that’s absolutely fine.

Now that you know how to successfully manipulate your searching tools to the best of your ability. It’s time to consider whether you want to fly a budget airline or not. If you’re a person who absolutely needs to have that extra legroom or all the bells and whistles of a luxury liner, then you can just skip this section.

Budget airlines are a bit tricky to find as they’re not gonna always show up in the searches listed up above. This is where you’re gonna have to do some digging whether it be through travel forums on Facebook or by being the worlds best Google detective.

Here are some major points that need to be made clear ahead of time.

  1. Do not book anything whatsoever until you’ve read reviews online and read that fine print!

  2. Make sure your ticket is printed out before you arrive at the airport. Trust us, Jim once had a flight from Bucharest, Romania to Athens, Greece and tried to check-in online and it wouldn’t let him do so. He thought it’d be ok to show up at the airport and they’d help him print it out. WRONG! Ryanair charged him 45euro for not checking in, and 15euro for not having a boarding pass, anyone who knows the prices of Ryanair knows just these charges alone are 4x more than the flight cost itself.

Tip: if you’re going to book the cheapest flight that you can absolutely find, it’ll always help to make Google your best friend, do your research, and know what you’re getting yourself into. Jim says this after not looking at a layover that left him in an airport for over 24hrs!

Other helpful sites to use to your advantage!

  • Kiwi.Com ( while it offers very low prices sometimes, it comes with extremely high risks! In particular they put together extremely tight connecting flights in busy airports with multiple companies leaving it almost completely up to luck and chance. Yes, if you miss your flight, they’ll accommodate you. But it’s a task and a half and we hope you don’t have anywhere to be the next day)

  • SecretFlyer – a site which makes its money off the mistakes of other companies and airlines. Some days they’ll find airlines which have flights posted for $1 by mistake and sometimes it will find you half price flights…regardless it’s one of those sites you should be checking daily!

    Pro Tip: If you download their app it will automatically send you updates instead of having to check the site every day. They also allow you to do custom notifications if you chose to pay the $1.99/month however we recommend you trying it out first before you make any commitments like we suggest everything else.

  • Finally sometimes just checking the actual airlines website for the prices is the best way to do it. They love web traffic going directly to their site just like every other one of us do, and to do so they have to offer deals as well.

    Flying with kids? No problem! Get yourself prepped before that long flight.

Bonus Content:

Looking for incredible deals for the holiday season? Don’t have the time to commit to checking all these sites for the best deals and want to days of the year where you can almost guarantee to get the lowest prices you possible can?

Each year we’re given 2 days of the year where you can purchase tickets for extremely low prices aside from the high fees and taxes that come along with ticket price. The 4th Friday of November (Black Friday) which is the day immediately following the Thanksgiving holiday in the United States, and the Monday immediately following that (Cyber Monday). Over the past 5-10 years Cyber Monday has now turned into the biggest shopping holiday due to the closure of so many shopping malls and all of the purchases coming from online retail outlets with free delivery to your home.

Pro Tip: With the exception of the peak summer season, to some degree it’s easy to find cheap flights from US cities to the European hubs like Athens, Paris, Copenhagen, Milan and Amsterdam.

Here’s a list of the top 25 airlines that’ll be offering Cyber Monday deals through Skyscanner on November 22nd:

American Airlines, Delta, United Airlines, Aeromexico, Cathay Pacific, Iberia, Alaska Airlines, Norwegian, Singapore Airlines, Southwest Airlines, WOW Air, Air China, Emirates, LATAM, LOT, British Airways, Virgin Atlantic, Virgin America, Jetblue, Spirit, Air France, Portugal, Hawaiian, Turkish Airlines, Frontier, TAP

Remember the peak time to purchase your tickets that day will be around 9:00 a.m. EST and the worst time would be 5:00 p.m. EST per the statistics of the last 2 years on Cyber Monday. Make sure you’ve got Skyscanner mobile downloaded ahead of time so you can work your way around it with no problems the day of the sale.

We will keep going back to this!

The more detective work you do, the better the outcome you’re going to have in the long run. When deciding a destination for the upcoming year, do searches like “cheapest travel destinations 2019” or “backpacking destinations on a budget 2019”. We promise you that these will do nothing but benefit you in the long-run. This is how Jim ended up finding flights to Colombia from New York City for $220/rt a few years ago, and $500/rt to Thailand from New York City.

Other Resources:

Now that you’ve booked a flight or you’ve got the resources to do so, it’s time to figure out what it is that you’re going to do for accommodation! We’ve compiled a few of our favorite and most reliable companies to book through.

Now it’s time to make sure you know how to properly utilize your time at the airport!

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