The Complete Guide for Booking the Cheapest Flights (Part II)

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Part 2 of the guide for booking the cheapest flights is finally here.

The 1st part of the guide was just a warmup for the real deal – and here it is.

Some of the tips in this article may seem a bit unconventional (and a little crazy), but they work. 

So enough with the babbling. Let’s jump right in.

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  1. Deconstruct your itinerary

    Who said you should blindly trust the airline’s proposed flight?

    It’s true that online flight aggregators & airlines do a pretty good job finding cheap flights for us. But did it ever occur to you that you might be overpaying, just because the airlines’ flight search algorithm is designed to simplify your booking process? 

    Let me give you an example. Let’s say you’re searching for a flight from NYC → London, and you found a relatively cheap flight with a layover in Iceland. Obviously the airline or flight aggregator will show you the full itinerary, and it doesn’t require you to book these 2 flights separately. Why would they make you go through this hassle, right?

    But wait a minute…
    “What if i booked those flights separately? Will it cost the same?”

    Actually, in many cases, it will be cheaper.

    Kind of funny huh? Same airline, same flight, same hours – for less money, just because you deconstructed the flights and booked them separately. I’d say that’s a pretty good deal for the average bootstrapper.

    Key Takeaway: Going the extra mile of deconstructing the flights you find online & clicking your mouse a few more times can land you a cheaper deal than just blindly clicking “Book Now” on the suggested flight.

  2. Extend your layovers

    Here’s a pro tip for you Travel Freaks out there.

    We talked all about flying indirect, combining multiple airlines and flying low cost. Now’s time to go one step further.

    Usually when we fly indirect – we automatically look for the shortest layover available, and the flight search engines does it’s best to filter them for us.

    But wait, let’s take a step back. What if there’s a cheaper connecting flight a few days later (and there usually is)?

    Let’s take the same NYC → London flight example, with a layover in Iceland (i’m a sucker for Iceland). Instead of spending a few hours staring at the beautiful landscapes of Reykjavik from the terminal windows, why not extend your layover for a few days (or anywhere else for that matter) & go pay the volcanos a visit?!

    And here’s the funny thing – even if there are cheaper connecting flights a few days later, you probably won’t even see them pop up in the search results, because flight search engines and airlines try to give us the shortest layovers possible. They don’t bother showing us a connecting flight that departs 4 days later.

    But they don’t realise we’re TravelFreaks – we don’t mind spending a few days in the layover country (in some cases).

    Key Takeaway: Layovers can be more than just pit-stops on the way to your final destination. Longer layovers can dramatically reduce your flight costs, and you can end up having a lot of fun in the process.

  3. Use a travel credit card

    Travel Credit Cards

    Credit: frankieleon

    There are so many travel credit cards out there it’s ridiculous… Credit card issuers & airlines try to entice new customers with special perks and giveaways, sometimes HUGE giveaways.

    Some of these benefits include:

    • Frequent flyer bonus miles (sometimes it’s A LOT, and you can book a flight just by signing up)
    • Reduced or NO foreign transaction fees
    • NO annual fees
    • Cash-back
    • Extra points for each dollar you spend (some offer 3 points per dollar)
    • Low spending minimums
    • In-flight upgrades: first/business class upgrade, priority seating, free luggage and more
    • Special deals and bonuses with airlines, hotels and travel activities
    Pro Tip: To choose the best travel credit card that meets your needs, i highly recommend you check out Brian Kelly’s (aka The Points Guy) list of recommended airline cards. 

    Key Takeaway: Signing up for a great travel credit card is one of the best things you can do to fly for cheap. The best thing for us mere consumers is that competition between credit card issuers is fierce, which results in better deals for us! So keep an eye open for special deals and offerings. They appear pretty often.

  4. Is Tuesday really the cheapest day to book your flight?

    There is a common belief that Tuesday is the best day of the week to book your flight.

    Well, is it true?

    The answer to this question isn’t really a “Yes” or a “No”. It’s sort of a it’s a “it can be, but it
    doesn’t have to be” kind of answer.

    Sure, if you’re booking a ticket for the upcoming weekend (which you should avoid doing in the first place), then yes, booking your flight on Tuesday might give you a better chance to catch the cheapest flight fare, compared to the rest of the week..

    But people make the mistake of thinking that Tuesday is some magical day where tickets suddenly become cheaper. Sorry to burst the bubble – it’s not.

    The reality is that there are way too many factors that cause flight fares to fluctuate, regardless of what day of the week it is. That’s why I don’t recommend spending your entire Tuesday on booking sites hoping to find sweet deals. It’s an amazing way to waste your time.

    “Well then Mr.Genius, what do you suggest i do?”

    Take a look at the next tip!

    Key Takeaway: Flight ticket prices are affected by a lot of reasons, not simply by what day of the week it is. There might be a correlation between the two, but not necessarily a causation. Therefore, don’t blindly think Tuesdays will land you the best deal. Flight prices are way more complicated than that.

  5. Sign up for price change alerts

    A much better approach to keep an eye on the market & spot price drops is to sign up for flight alerts.

    Flight aggregators such as Momondo, Skyscanner & Hipmunk do the monitoring for you, and update you when a flight price you’re interested suddenly drops.

    Skyscanner Price AlertHipmunk Fare Alert

    Pro Tip: When you get a price drop alert, make sure you do a quick check on other flight aggregators as well. It might be that they also updated their flight fare, but they don’t have a price alert service to let you know about it.
    Key Takeaway: Register for price alerts for the flights and destinations you’re interested in. Stop refreshing your browser like a mad man!
  6. Use student discounts

    Are you a student? Maybe it’s your lucky day. There are several websites out there that care about you & offer special flight deals to students. The most popular ones are STA TravelStudent Universe & Generation Fly. 

    Key Takeaway: If you’re a student, that makes you special! Try checking if a special someone like yourself can get a student deal on one of the websites above.

  7. “Same airline, same flight – different price?!”

    Yep, that’s what happens most of the time actually.

    You see, different flight aggregators work with different travel agencies, and therefore display different prices.

    Let’s take a look at a live example of this.

    Take a look at this Norwegian Airlines flight from NYC → London.

    On SkyScanner:

    Skyscanner London - New York Flight

    On Momondo:

    Momondo New York - London Flight

    As you can see – Momondo gives us a cheaper fare for this flight from BravoFly,which doesn’t show up in SkyScanner. Plus, you can see that Momondo has +22 more options to offer us for this flight, while SkyScanner only has 5 other offers. One flight aggregator might be working with a 3rd party travel agency, that doesn’t work with another flight aggregator.

    Pro Tip: Sometimes flight aggregators collaborate with 3rd party travel agencies on a per-flight basis. Meaning that for some flights the travel agency may appear in the search results, while for others they may not necessarily appear.

    Key Takeaway: Different flight aggregators work with different agencies, which ultimately affects the flight prices we are offered. 

  8. “Same airline, same flight, same agency(!) – different price?!”

    Here’s a puzzle:

    “How come flight aggregators show different prices when it’s the same flight, AND it’s the same agency!”

    WTF right?

    Well, not really if you think about it…

    When an airline or a travel agency collaborates with a flight aggregator – both sides close the deal and agree on their own terms & agreements. And as you all know – no deal is ever the same in the business world. Different deals between flight aggregators & airlines/travel agencies result in different flight fares for the exact same flights. Kinda makes sense doesn’t it?

    Let’s take a look at the following example (did you notice it’s the same flight every time?)Skyscanner New York - London Flight 2Momondo New York - London Flight 2

    Same airline, same flight, same agency (eDreams in this case) – different prices.

    Key Takeaway: Different flight search engines show different prices, even for the exact same flights sold by the exact same agency. That is why it’s best to compare flight fares on different flight aggregators before booking your ticket.

  9. Don’t rely solely on flight aggregators’ pricesCache Solves Many Problems

    You search for a flight, and then BOOM – in just a few seconds you get a huge list of flight options from a huge list of airlines & travel agencies.

    Ever wondered how come flight search engines are able to retrieve all these flight fares from all these different travel agencies & airlines so quickly?

    Let me tell you how.

    They cache the flight fares.

    This is what Gareth Williams, CEO of Skyscanner said when asked how they keep the prices up to date:

    “We cache all the prices that we get, but some will still be out of date by the time they appear in search results on Skyscanner.”

    You may be wondering what the hell all that means, and why do this weird thing if prices are out of date? Let’s ask the geek for his opinion:

    The Geek Explains: Flight aggregators don’t retrieve all the prices in real time. The reason is because doing so means that every time a user searches for a flight, they will have to depend on every website they are querying to return the flight details extremely fast so that the customer (you) doesn’t grow old by the time he gets back the search results.

    This simply isn’t scalable, and it will simply take too long.

    Instead, they query the 3rd party websites periodically,  and save the prices on their own servers (aka caching). Then all they have to do is return the last-updated flight details from their own servers, which is a lot faster and a lot more scalable.

    Search aggregators prefer paying a (relatively) small price of showing outdated fares for increased speed & performance.

    Let’s see it with our own eyes:

    Note: I used SkyScanner for this example, but this holds true for any flight aggregator (that i know of).

    A round-trip flight search in SkyScanner from New York → London returned the following result:

    Outdated Flight - Skyscanner

    As you can see, the good thing about Skyscanner, is that they tell you whether the listed flight quote is up to date. In this particular case, you can see that the price they are listing is not – it hasn’t been updated for the past 3 hours, which is pretty long, considering the volatility of flight prices.

    I ran the same flight search later, but this time i chose a one way trip.

    Skyscanner New York - London Flight 2

    Sure enough, it found the same Norwegian Airlines flight. You can see that now it claims to be a live quote. Is it really?

    Let’s proceed to the booking page in the seller’s website (eDreams in this case) to find out.

    eDreams New York - London Flight 2

    Would you look at that! The price is even cheaper than what SkyScanner quoted me! (£151 = $229 the day i wrote this post).

    You can see that eDreams were smart enough to tell me that the price differs from the price i was
    originally quoted with, but not every website does that.

    Note: Obviously outdated prices can go the other way and cost more. I just got lucky with this one, but so can you if you dare go down the rabbit hole!

    Key Takeaway: Prices displayed in search aggregators can be cached, and therefore outdated. Flight prices are extremely volatile. You should validate what the true price is by proceeding to the actual booking website.

  10. Cheaper ≠ better

    Don’t be 100% money-oriented. 90% is also fine.

    If you find a non-stop flight that costs just a few bucks more than a flight with a layover
    – pay the few extra bucks. Your time is worth more than that.Skyscanner Flight New York - London 3VSSkyscanner Flight New York - London 4

    PAY THE DAMN $8!

    Another example is low cost airlines VS traditional airlines. Sure, low cost can be great. But is it always better than “normal” flights?

    It depends. A lot of times it’s not. We’ll see why next.

    Key takeaway: Don’t be too hasty when you spot a cheap flight – there might be a better option out there. Better can be a direct flight VS indirect, a good airline VS a sucky airline, low cost airlines VS regular airlines, better available seats VS no free seat choice (i’m willing to pay a few extra $$ for a window seat in a 10 hour flight).

  11. DYFH: Read the small letters

    DYFH = Do Your F*cking Homework.

    Doing your homework means paying attention to the small details.

    When you book your flight, you need to be aware of all the hidden costs, paid services, and
    premium addons. Avoid any unpleasant surprises that might arise.

    Flying low cost? Well, ain’t sh*t for free. Read the small letters to figure out exactly what costs extra:

    • Does the price include taxes?
    • Does the price include services you don’t need? Some airlines try to automatically include
      things you don’t need (like travel insurance) that bump up the price. Make sure there are no marked checkboxes that increase the price, and uncheck them if not needed.
    • Carrying extra weight? (Don’t!)

      If you do – check the airline’s luggage & carry on guidelines. Low cost flight prices usually don’t include checked in luggage, and carry-on also has weight limitations. Make sure you’re aware of them and take them into consideration when comparing flight prices.

      Pro Tip: Yes, i’m reminding you again – P.A.C.K L.I.G.H.T
    • Most low cost flights don’t include a free meal. Make sure you read what is served on the
      flight, and prepare accordingly.
    • Does seat selection cost extra?
    • When flying low cost – there is a good chance you will be flying from/to an alternative
      airport. Arriving at these airports can take more time & money. This extra overhead can make the deal look not so appealing anymore.

    Key Takeaway: Remember: DYFH. This includes reading the small letters and uncovering hidden costs. Always be prepared and don’t get caught of guard.

  12. Did you pay too much for your flight? You can still save your money

    It's Not Too Late Yet

    According to Fairfly, 88% of us don’t check flight prices after we book. Why bother, right? It’s probably too late…

    No it’s not! You can still save your money if a cheaper alternative happens to come along – even after you booked your flight!

    A mobile app like FairFly helps you do just that.

    You simply send them your flight ticket, and they keep looking for cheaper alternatives after you booked your flight. If they find a significantly cheaper alternative for you – they help you cancel the original booking and help you book the new one instead.

    The great thing about FairFly is that they only make money if they’re able to find you a cheaper flight, in which case they take a small percentage of the money they saved you. Win-Win.

    Pretty cool huh?

    Key Takeaway: Use a service like FairFly to help you keep an eye open for cheaper alternatives after you booked your original flight. They might save you a nice chunk of money, even after you purchased a more expensive ticket.

  13. Look for air passes

    What the hell is an air pass? It’s actually pretty similar to a buss/train pass – except it’s in the air.

    The idea is simple – if you’re planning to visit multiple cities in a specific region or country (South America, Europe, Australia, Brazil, Japan etc’), instead of purchasing tickets individually for each flight, you can purchase a discounted air pass that is tailored to your itinerary.

    Air passes are not widely marketed by the airlines offering them, probably due to it’s complicated structure. That’s why you can’t book most of them online. You usually have to contact the airlines directly to check whether they have an air pass available and what the conditions are. 

    Airlines & alliances that offer regional/domestic air passes include:

    Oneworld – Worldwide 

    Star Alliance – Worldwide 

    Sky Team – Airlines

    Qantas Airways – Australia

    Gol Airlines – South America

    TAM Airlines – Brazil 

    Aerolineas Argentinas – South America

    Nature Air – Costa Rica

    Japan Airlines (JAL) – Japan 

    Note: Air passes are available only for residents outside the region you plan on visiting. For example if you live in the U.S, you can’t buy a North American air pass.

    Pro Tip: Air passes aren’t always worthwhile. Every airline has their own terms and conditions regarding the flexibility of the air pass, the duration, the region coverage etc’. You should contact the airline directly to discuss the terms and conditions of their air pass.
    Pro Tip 2: Don’t be afraid to negotiate for better prices and terms. Air passes are flexible in their nature. There’s no reason why the price should be any different.

    Key Takeaway: Air passes are a great solution if you’re planning a trip to multiple destinations or across an entire region. Doing your homework is especially crucial when booking an air pass. Make sure you understand the terms and conditions of each air pass. It will help you negotiate for cheaper prices.

  14. Use a travel agent

    You’re probably thinking:

    “What? are we back in the 90’s? Why the hell do i need a travel agent?!”

    Stop being so negative!

    Sure, we live in the internet era. But that doesn’t mean you should rule out traditional travel agencies, especially if you’re planning a multi-destination trip. It’s worth getting a quote from travel agents as well to get a bigger picture. They can probably give you some insights and tips you didn’t know about.

    However, that’s actually the not the main reason you’re calling them. What you want is for them to try to and beat the price you have found yourself during your research (you’ve done your research, right?).

    Let’s go over the process and see how travel agents can help us find cheaper deals:

    1. Do your own homework. Search for the cheapest flights you can find online. Use this guide as your reference.
    2. Call up some travel agents, but don’t mention any prices you’ve found yet. Let them do the talking and tell you what they’ve got to offer.
    3. If the fares they give you are way above what you’ve found – thank them politely, and call the next one.
    4. If they give you prices that are not that far from what you have found, tell them that you actually found cheaper alternatives yourself – and ask them if they can offer you something better. This makes them realise you’re for real, and that you actually put in the time to do your own research. They will take you more seriously, and you will motivate them to close a deal with you. And believe me – they want their commission.
    5. If they’re able to beat the price you’ve found, book with them. If not, call the next agency.

    Key Takeaway: Don’t ignore traditional travel agencies. They still have their place in the 21st century, but now they have to hustle to get their money. Use it to your advantage to try and squeeze a better deal.

  15. Book directly with the airline

    If you know where you’re headed – then you should always book directly on the airline’s website.

    The good thing about flight aggregators (at least the ones i recommended in the previous post) is that they don’t sell the tickets themselves. They let you choose where to book your flight. You can choose to book from travel agencies, but also from the airline itself, and therefore avoid paying extra fees the travel agency might charge.Skyscanner - Book with Airline

    Of course don’t forget that most of the low cost airlines don’t even show up on flight aggregators. The reason is they prefer not to pay the flight aggregators a commission & cut their profits even lower than they already are. This allows them to sell for cheap, and still retain pretty decent profit margins.

    Pro Tip: In most cases the airlines themselves will offer the cheapest flight fares. But even if not, the difference is usually marginal and worth the extra few bucks for your peace of mind.

    Key Takeaway: Always try to book your flight with the airline directly to avoid any middlemen, even at the expense of a few more bucks.

  16. Bonus Tip: Traveling with friends? Book each ticket separately

    Usually airlines sell a limited amount of tickets at the lowest rate. When those tickets get all
    booked, the lowest rate ticket price rises.

    So let’s say you and 5 other friends are traveling to Buenos Aires together. There is a chance that if you try to book 6 tickets, the total price will be higher than if you had selected 1 passenger at a time.

    Why is that?

    Let’s say the airline had 2 tickets left at the lowest rate of $250 each, and the next lowest rate is $300 (with a lot more available seats) – you will pay as a group 6 X 300 = $1800 instead of 2 X 250 + 4 X 300 = $1700.

    Pro Tip: First check that the flight even has 6 tickets available before attempting to get a better
    price by booking individually. Then check to see if selecting 6 tickets individually results in a cheaper price.

    Key Takeaway: Break the group to score lower prices. If some of you got cheaper prices than the rest, don’t be **sholes and pay them the price difference so they don’t get screwed.

Wrapping up + Next Steps

“I fear not the man who has practiced 10,000 kicks once, but I fear the man who has practiced one kick 10,000 times.” – Bruce Lee

Even though this guide is packed with information on booking the cheapest flights, i don’t recommend you start implementing all of them. Instead, focus on the ones that make sense FOR YOU, and learn to master them.

Use this guide as an arsenal of tools, not as Batman’s utility belt. 

To make it easier for you to return to this guide when in need, i combined the 2 parts into one extensive PDF guide you can download & carry with you offline.

So go ahead and:

  1. Download the full guide for booking the cheapest flights from the big download button below.
  2. Save it in your Evernote/DropBox/Email account.
  3. (Recommended) On your phone/tablet –  make it available for offline access so you can return to it when you’re traveling.
  4. Leave a comment & let me know which tips you found the most useful, and what other tips you have for booking cheap flights i haven’t covered here. Who knows, there might be a part 3 🙂
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