Hacking the Travel System, An Interview With Matt Bailey

Travel Hacking
Travel hacking doesn’t have to be stressful or confusing thanks to Matt Bailey of Canadian Free Flyers.

Many people tend to look at travel as a luxury, one that requires a lot of money. I’ll be the first to admit that I’ve found myself thinking this exact same way from time to time. But what I’ve come to realize over the years is that it doesn’t have to be as expensive as one thinks and there are a number of ways to save money before and during your travels. Reducing your overall costs are one thing, but what if I said that you could be earning free flights and accommodations just by going about your everyday life? It’s true!

Recently, I came across this concept called ‘travel hacking’ and found there’s a whole subculture of travelers who have discovered ways to score free trips just by using their everyday spending habits to their advantage. I wanted to learn more about this practice, so I contacted one of my fellow Canadian Travel Bloggers, Matt Bailey, to explain what ‘travel hacking’ means and how his site Canadian Free Flyers has been providing its members incredible deals and travel opportunities since 2012.

First off, tell us a bit about yourself and some of your travels.

I’ve been traveling almost full-time since 2009 when I took my first long-term trip to New Zealand and Australia. It was a long-time dream of mine to visit Australia since I was a teenager and it took me six years to finally live it. Once I experienced solo travel, I was hooked. Since then, I’ve met my soon-to-be-wife and we have traveled all over Canada, the United States, Mexico, China, Myanmar, Malaysia, Thailand, Indonesia, Cambodia, Laos and the Philippines. I’m big fan of really exploring a country. I tend to visit cities for a short time before heading out to explore more remote areas and beautiful landscapes.

My first ‘travel hacking’ trip was to Mexico City. My fiancé and I wanted to go visit her family (she is from Mexico City) but we also wanted to visit some friends in Texas and see Chicago for the first time. After spending only six months earning points, we managed to travel to Mexico City along with a four-day stopover in Houston and a 23-hour layover in Chicago all for the price of one.

Collecting frequent flyer miles for travel.
Matt, his fiancé and her family of their first travel hacking trip to Mexico City.

One of the travel sites you run is Canadian Free Flyers, which aims to help Canadians hack the travel system and get more bang for their buck. For those who aren’t familiar with this term, what does ‘travel hacking’ mean?

Travel hacking is basically the art of low-cost travel. The “bread and butter” of travel hacking is figuring out methods for earning hundreds of thousands of frequent flyer miles and learning how to redeem them for high-value trips. Travel hacking also deals with finding low-cost or free accommodation and even rental cars and other methods of lowering the cost of a trip.

Where did the concept for Canadian Free Flyers come from?

I first learned about travel hacking from different eBooks I purchased online. After applying some of the tactics to Canada, I earned enough for a free flight to Mexico. However, after joining other travel hacking membership sites, I realized all of them were geared towards Americans.

I got frustrated with offers after offers that were only available for Americans.  With that in mind, I began searching for my own Canadian-specific deals, which lead me down the road to what eventually became Canadian Free Flyers; an online travel hacking membership site specifically for Canadians.

How does the site work?

Canadian Free Flyers is a paid membership site that sends all the deals right to member’s inbox. After talking with many people that were interested in earning more points, it became clear that many didn’t want to spend the time to search multiple blogs and websites to find deals for earning flight and hotel points.

Members of Canadian Free Flyers don’t need to do any research whatsoever. I do all that for them and when I find a deal for earning frequent flyer miles or hotel reward points, I send it out to everyone. Members can then choose if the deal is suitable for them or not.

Aside from the real-time deal alerts as mentioned above, members also have access to dozens of tutorials that explain everything there is to know about Canadian travel hacking including the various methods for earning miles, how to redeem them for the best value, how to get two or three trips for the price of one, how to get half-price 4-star hotels, how to find free accommodation all over the world and much more. These tutorials are available 24/7 and are constantly being updated whenever new methods are found.

Travel hacking deals for Canadians.
Feeling excited on Komodo Island, Indonesia.

What is the biggest advantage of being a part of a community like Canadian Free Flyers?

The biggest benefit is learning and earning enough frequent flyer miles for free trips all over the world as well as saving time by not having to do any research at all. It’s also a great way to stay motivated and not forget about earning points.

By having all the research done for you, you don’t need to worry about missing a deal or wondering whether it’s legit. It’s like having your own personal assistant scanning the web for frequent flyer miles and hotel reward promotions!

What kind of individual would get the most out of Canadian Free Flyers?

Anyone who wants to travel and is willing to spend a little bit of time to go after the deals I send will benefit from Canadian Free Flyers. It also helps to be willing to apply for at least one credit card. Another thing I should mention is that members should be willing to remain a member for at least one year to see the full benefit. Obviously, I hope they remain much longer. Deals come and go on a consistent basis but sometimes there might be three deals in one week and other times there might be just one deal over two weeks.

After doing this for years, I know that the deals do come and anyone can earn enough points for at least one free trip every year, if not two or three. They just need to be willing to commit and be patient.

What has been the biggest or greatest reward the site has featured?

Some of the greatest rewards come from credit card offers, which are fast and lucrative. One of the best credit cards was a 30,000-point offer with no fee for the first year.  There are many great credit cards out there and they can really help with earning frequent flyer miles on a big scale.

I also remember a promotion that Aeroplan was hosting at Sobeys. Basically, customers had to make around 30 transactions during a specific time frame. After reading the fine print, I realized there was no dollar amount specified. This meant that customers could buy something as small as a chocolate bar and do it 30 times. For about $50 or less, you would have earned 15,000 points, which is enough for a short-haul flight. Not bad if you ask me!

Scoring free flights with credit card reward programs.
The ancient city of Bagan in Myanmar.

So really, what’s the catch?

There’s no catch. All that is needed is the willingness to actually capitalize on the deals and the patience to stick with it over time. The ability to apply for a credit card or two will certainly speed up the process but isn’t an absolute requirement.

And lastly, what if I’m not sure if this is for me? Can I try it out first before committing?

Right now, Canadian Free Flyers actually has a new $2 two-week trial, which makes it easy to test it out and see if it’s right for you. If you’re not pleased with what you see, simply cancel the membership before the two-week mark. You can cancel any time with no penalty. I hate contracts as much as the next guy.

After the trial, Canadian Free Flyers comes with a one free flight guarantee. After one year of membership, if we haven’t sent enough deals that would add up to the equivalent of one free flight, we will refund every last cent. We know we’ll send more than this but members need to actually capitalize on the deals if they want the points.


Matthew Bailey is a vagabonding entrepreneur and writer who is currently traveling around the world with his wife. You can find his writing at LiveLimitless.net and his photography on Instagram (MatthewGBailey). You can also follow him on Twitter @MatthewGBailey.