Friend: “Guess how much I paid for my flight to Europe?”
You: “$400?”
Friend: "Try again”

We all have that friend that is constantly bragging about travel exploits. Among our friend’s extraordinary feats are, of course, cheap flights.

Or maybe it’s the other way around, maybe we’re the friend that loves showing off when a good deal comes around.

Regardless of the position we’re in, we all love getting sweet deals on flights. We can also get extremely jealous (depending on personality) when others we know are having the time of their lives abroad without creating a black hole in their bank account.

Today, more than ever, we should be in a good position to consistently get the best deals on flights. In fact, airfares have fallen by 50% in the last 30 years. Furthermore, long gone is the era when your only solution was the airline ticket booth or the neighborhood's travel agent's store. Through a plethora of tools, modern travelers can now book flights online on their own and in a way that's never been simpler.

Ironically, however, sometimes it just doesn't feel that way. The average traveler (like myself) can sometimes feel that they're entangled in the webs of the online airfare industry.

Why do we sometimes feel this way?

Well, I can think of two reasons.

Have you found yourself with 10 different windows open comparing airfares from too many websites, only to close them all with a headache and frustrated that you won’t be the one bragging this time? Join the club. This is the first challenge I’ve experienced when shopping for flights online.

The second challenge for the average traveler is knowing whether the airfare they're looking at is a good deal or not. How can you know if you don't have anything to compare it to historically? What if the price spikes tomorrow? Even worse, what if I buy today and the price goes down at some point in the future? Although some booking tools offer price reduction refunds, this still isn't common practice for the majority of players in the online airfare booking industry.

We backtrack to January of 2017. I wanted to book a flight to Hawaii and was experiencing those very same challenges. Except this time, I had gone through the motions too many times to not do something about it.

An idea emerged. This one wasn't just another idea that went as fast as it came. It persisted, persevered and fought its way for a piece of my mind's real estate. It haunted me night and day.

The idea became a resolution, a goal. I was resolved to get a grip on this situation and create a process by which:

  1. I would have a proven and consistent method of booking flights online.
  2. I would know whether I'm getting a good deal or not.

The results of my research and experimentation have been a success thus far. I’ve been able to book a flight from Montreal (Canada) to Honolulu (Hawaii) for one of the cheapest prices possible given the dates I wanted.

In this article, I share my methodology and open it to the scrutiny of other airfare bargain hunters. Read on if you want a few tips that can put headaches aside next time you book a flight online.

DISCLAIMER: This article will not be teaching you how to fly for free. Most of us already have a very heavy schedule and cannot turn airfare hunting into a full-time job. This is for us "mortals" who can only dedicate a limited amount of time to finding the best deals possible. Furthermore, I do not claim to be the best at booking airfares. As much as I’m pleased with the process outlined below, there is still room for improvement (you’ll read more about this in the last section of this story).

The Good-To-Know Stuff

First off, we need to hash out some facts about how the online airfare industry works.

  • Prices are governed by the laws of supply and demand: if there is more demand (lots of customers) compared to a lesser amount of supply (airplane seats for a given route), prices will be high. Inversely, if there is a lot of supply to the point that demand is exceeded, prices will be lower.
  • Airfares are dependent on seasonality: prices will be high during high-season, and yes, you guessed it, low during low-season. Seasonality depends on the route and destination. The concept of shoulder season also needs to be defined: it’s right in between high and low-season. Shoulder season is when you’re likely to get the weather/conditions of the high-season, at low-season prices. Sounds interesting doesn’t it?
  • Airfares will vary in function of the departure and arrival date (which goes hand-in-hand with the laws of supply and demand). That’s why you’ve probably noticed that flights leaving or coming back in the middle of the week are usually cheaper.
  • Exchange rates will have an impact on how fares are priced. If you’re curious to know how that works, check out this link.
  • If you want to get an in-depth analysis of how the airline industry prices an airplane seat, here’s the link. It’s a fascinating and eye-opening read. I highly recommend it.

The Tools

Before we dive into the methodology, I will expand on the different booking tools I have found useful to book flights online. One thing to remember is that there is no such thing as the PERFECT tool/website. That's why we need to select a few tools to achieve our goals.

  1. Google Flights: I don’t know how I only found out about Google Flights earlier this year. I feel like I’ve missed out big time. Google Flights has dramatically redefined the way I shop for flights. To be honest, this tool gave me the inspiration to write this article. I love Google Flights because of its clean and user-friendly interface that gives you a rich amount of valuable information to make a good decision. It also allows you to easily track flights and gives you easy-to-read graphs that provide perspective on how prices are fluctuating through time. Something else about Google Flights: It’s a search tool ONLY. It means that you do not use it to actually book your flight. Google Flights will scour prices and then give you the link to purchase DIRECTLY with the airline (in some cases, through well-established travel websites but this is more of an exception rather than the rule). There are so many horror stories out there about travel intermediaries ripping customers off or doing everything in their power to ruin people’s trips that booking directly gives you a whole lot of much needed peace of mind. One thing to note though: Google Flights will not systematically give you the cheapest rate. Like I said before, a perfect flight booking tool does not exist. As much as Google Flights has become the cornerstone for my airfare online purchases, it is good to always keep it in check with other references. Therefore, Items 2, 3 and 4 below.
  2. Expedia: Expedia is a trustworthy and well-established flight booking site. Its reliability makes it a good candidate to double-check flights and see if there's a route/air carrier that was missing in Google Flights.
  3. Momondo: I have noticed that Momondo offers cheaper rates than the rest on average. The only downside is that it redirects you to other intermediary websites and not the airline’s website. I have yet to book through Momondo so I cannot speak neither for the quality of the service they provide, nor for their trustworthiness. However, they seem to have a very good reputation online and they're known for frequently being cheaper than the rest.
  4. Hopper: I have recently discovered this app and I love it so far. Much like Google Flights, it is very user-friendly and provides a feature that the tools above don’t: it gives you a prediction of how fares might fluctuate in the future, along with the recommendation whether you should buy the ticket now or wait a bit more. Although the accuracy of this data still needs to be verified, having this sort of analysis can prove to be very useful. Here’s a full-length review if you want to know more about this app.
  5. Local Deals Sites: this one does not have a specific name because it will vary according to where you live. In the Montreal area, I follow YUL Deals on Instagram. Whenever they find a new deal, they post about it and I've seen some pretty great deals on it.

The Process

Now we get to the nitty-gritty of how to use the knowledge and tools highlighted above.

First of all, depending on the type of person you are, either:

  1. You’re trying to decide where to go on your next vacation or
  2. You have a set destination in mind.

Regardless of the situation, your goal is to stick to your budget and find a great deal.

Person Type 1: Choosing destinations is so challenging. It can be compared to being in a restaurant where all menu items look amazing. “Do we have a taker?” Asks the server. Of course you don’t. Google Flights can be your menu for flights.

Once you log on, go to the menu tab on the left and choose “ Explore Map”. Next, choose approximate dates for when you want to travel. Now’s the time to refine your geography knowledge and look at a world map that will look something like the image below. You can zoom into the different regions of the world to see how much it would cost to go there given the approximate dates you entered. Once you get an idea of where you want to head, your scenario becomes the same as Person Type 2.

Person Type 2: If you know where you want to go, next step is to find out when’s the cheapest to go. The starting point is Google Flights once again. For example, say I want to go to Indonesia this year and want to see when’s the cheapest time to go. I log onto Google Flights, put the departure city (Montreal in my case), the destination (Jakarta, the capital of Indonesia), and for now we’ll use a random date, and a somewhat specific time interval with the wished duration of my trip. This is what we have so far for a 14-day round-trip from Montreal to Indonesia:

As you can see, Google Flights already gives you an indication of what the price is for such a trip in June and July. Lowest price is around $1,300 and highest is $2,482. Yikes. We can do a lot better than that.

Next step is to go on the “Price graph” tab, which brings up the following visuals:

The bottom-graph does show that June-July seems to be high-season in Indonesia because prices are on average higher than the rest of the year. We can see that the graph bottoms out Mid-November 2017. This makes a lot of sense because October-November usually marks the beginning of the rainy season in Indonesia. Since getting rained one is nobody’s ideal vacation, I don’t really want to buy a ticket then. The graph shows that pricing for the months of September-October ispretty close to November. We call September-October shoulder-season: right in between high and low season, when you still have high chances of beautiful weather, but less crowds and cheaper prices. Let’s take a closer look at these months by moving the cursor over in the bottom graph.

Now that looks much better. We’re way below the $1,419 price line for the original selected dates. On the first graph, we can now look at the details by seeing the way price fluctuates according to the date of departure.

The lowest fare I found is $1,030 leaving on the 30th of September (Saturday) and coming back on the 14th of October (Saturday as well). $1,030 to go literally to the other end of the world doesn’t sound so bad. Sounds like a good fare but it isn’t brag-worthy quite yet.

At this point, I select those dates and start playing with the departure and arrival date to see if I can go even lower on the price. I find out that if I come back on Friday October 13th, price drops to $1,015. Getting closer to finding a flight for under $1,000.

This is where we need to start tracking the price. We do so by enabling the toggle as pictured in the image below:

It is good practice to track a few different dates because some date intervals are much more subject to price fluctuation than others.

Now, we can head to Expedia and Momondo to double-check what our different options are. Expedia gives me the following results:

$1,067 for a United flight. Pretty much in line with what we saw on Google Flights.

Now Momondo:

Bingo! Under $1,000! Nevertheless, take into account that if you choose this flight, you’ll be booking through Fareboom, a travel intermediary. If a problem arises, you’ll have to deal with them AND the airline. Spending $100 to buy a flight directly with United is completely understandable because it can give you more peace of mind. $966 to fly a distance of nearly 20,000 miles (32,000 kilometers) round-trip sounds pretty good to me.

We’ve already made a lot of progress. We still need to have some knowledge regarding how prices will fluctuate in the future. We turn to our Hopper app.

Hopper gives us the following information for our trip:

Hopper is telling us that we should book now because prices are likely to increase in the future.

Now we have to make a judgment call. We can defy the odds and hope for an unexpected drop in prices or we can terminate the process and choose to buy the ticket.

Apparently, we’re better off buying now because this price is as low as we’ll get. Remember, this is not set in stone. It’s simply a forecast. Depending on your appetite for risk-taking and living on the edge, you can decide to defy the odds and let some time go by while tracking the prices hoping that an unforeseen change in the future will bring a drop in price.

In some cases, Hopper will tell you that it’s better for you to wait, because you’re likely to get a better price. What should you do then?

Here we stop the imaginary scenarios and we go back to the Hawaii story.

For my trip to Hawaii, when I first started looking at tickets, prices were around $850. I was convinced I could get a better price. So I tracked two different dates on Google Flights and the waiting game began. First of all, look at the graph below (pulled from Google Flights). Can you see how important it is to track different dates? Flights leaving on Wednesday seemed to be much more dynamic price-wise. Second, looking at the graph below, can you guess when I bought my ticket?

Yes, that drop 12 days after I started tracking the flights! The ticket dropped to $647 (Canadian Dollars) and stayed at that price for only two days, after which it climbed back to an average of $800. I felt really good. I knew I had gotten a good deal because it was the lowest I had seen prices since I had started tracking it and since I had been casually looking at flights to go to Hawaii (2013)! Everything was good. Periodically I would check the tracked flights, just to pat myself on the back and say: “you've done well.”

Until this happened a few weeks before my trip:


I would be lying if I said that everything felt ok. EVERYTHING WASN'T OK.

Prices had dropped to a mere $547 ($100 less than what I had paid). That's $547 round-trip to travel close to 10,000 miles (16,000 kilometers).

Of course the first thing I did was call United Airlines to talk my way into this better deal. I was only received with the customary $200 USD price tag for an itinerary change.

"But I paid a lot more for the same trip!" I said with the saddest of tones I could muster.

"Fares vary according to the demand sir, there's nothing we can do about that". Answered the customer service representative in the firmest of tones.

Who was I kidding? I knew this was going to happen the moment I picked up the phone. I was bested by one of the first elements I explained in this story: the laws of supply and demand. A tear-worthy situation if you ask me (first-world problems… I know).

The Takeaways

After a few days, I was able to think clearly again. In retrospect, I don't think I could have done much about the aforementioned incident. I wouldn't have been able to not have a ticket 2 weeks before my requested time-off from work. It wouldn't have been nice to keep my hosts hanging for accommodation until the last minute. Above all, I love having clear plans ahead of time.

Furthermore, as much as you can learn to spot opportunities in the airfare market through variations in supply and demand, it is foolish to think that you'll be able to systematically cheat the whole system. You can make the best out of it, but you cannot beat it.

So if you ask me, would I have done things differently?

My answer would be no.

Given my personality (adverse to uncertainty) and life-imposed constraints, I still believe I got one of the best prices I could.

Remember the disclaimer at the beginning of this guide? Now that you know the full story, I cannot claim that the process I’ve highlighted above will get you the absolute cheapest ticket every time. Sometimes the price will dip one day before you leave (in my case, 2 weeks before I left) and there’s nothing you can do about that . However, through this process, you’ll be able to gain a lot more clarity and knowledge to let you know when you should purchase your ticket. I’m also a big-believer that if someone claims to have the PERFECT tool or process, that claim is false because in this world, nothing man-made is perfect.

Some other takeaways to keep in mind:

  • Do not travel in high-season. Try shoulder-season, during which you’re likely to get fantastic temperatures and weather, but less crowds and cheaper prices. Do research on your destination to find out when that would be. If you must travel during high-season, you must conform to the idea that you will be most likely paying a premium. But hey, deals still exist even then.
  • The first time you book a flight for a particular destination, you’re not likely to book at the best price. That’s simply because you don’t have as much background information as you would if you had already done it before. Case in point, first time I booked for Hawaii two years ago, I paid around $850, and I thought it was a good price. Now I paid around $650. Next time, before I commit, I’ll know better and wait until the prices bottom out at $550. Once you have some experience with a particular route, that’s when you’ll start having the most success.
  • To get around the point made above, if you’ve never booked a flight to a particular destination, talk to friends/acquaintances that have gone to the same destination in the past. Ask how much they paid for their ticket. These anecdotal facts, coupled with the research tools highlighted in this guide will help you stack the odds in your favor. One word of caution: beware of the friends that love bragging a bit too much and are willing to exaggerate the facts. We all know you didn't ACTUALLY pay $200 to go to Europe Brad (meet Brad, he's our imaginary bragger friend).


As I’m sitting on the plane to go to Hawaii, I cannot contain my excitement. 10 days of solid surf and sun with a side of good company await. I take a last look at my Google Flights chart.

Not bad. Although I could have gotten a better deal, I’m definitely below average. Maybe I need to develop a bit more appetite for uncertainty and wait it out a bit longer next time. Not sure I want to go down that road just yet. Remind me, how did booking flights become so entangled with reflections on my personality?

It’s 7:11AM and the plane is taxi-ing to the departure strip. It was supposed to leave at 6:35AM. I better not miss my connecting flight. Surf’s up and I’ve missed the ocean life for way too long. I can almost taste the salty water and feel the burn on my skin.

As I'm pondering over the fun-filled days that lay ahead of me, the two ladies next to me ask if it's my first time going to Hawaii.

As the conversation progresses, I ask:

"Hey, if you don't mind me asking, how much did you pay for your flight?"

"Ugh. $850." Lady 1 replies.

"Canadian or American?" I probe further, already thinking that either way, she overpaid.

"American. How about you?"

I struggle to do the math but I finally get there.

"At the current exchange rate, that's close to $1,100 Canadian…" I think to myself.

As much as I try to fight the smirk that's lurking on the corner of my mouth, I've already lost the battle. If only I could keep a poker face.

I guess my buddy Brad and I can be alike sometimes.


UPDATE — JULY 18TH, 2017

Wanna see how our flights for Indonesia are fluctuating? Check out the graph below. Prices have gone as low as $925!