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How to Grab Cheap Airfares with These Best-Kept Travel Secrets

Rob Nightingale 11-09-2015

It’s impossible to argue against Lao Tzu’s famous quote, “the journey of a thousand miles begins with a single step”. But it’s very possible to argue against the idea that the journey of a thousand miles begins with a wad of cash. In fact, travel need not cost you any cash at all.


There are a band of “travel hackers” out there, gaming the system. They’re pouring over small print, finding strategies, deals, and loop-holes that provide them with nigh-unlimited, free (or extremely cheap) hotel stays, flights, and travel experiences.

We spoke to two such travel hackers to offer you an overview of what travel hacking is all about, what you can expect from it, and how you can get started yourself, stress free Stress Free Travel: How to Prevent Mistakes and Minimize Anxiety Wouldn't it be nice if traveling could be a blissful affair? With a healthy dose of technology and a few tweaks to your traveling mindset you can banish all anxiety. Read More .

Meet The Travel Hackers

Travel Hackers

Matt Bailey

In his own words, Matt Bailey — see the photo on the left — is a “regular Joe from a small oil town who wanted something more”. Matt’s numerous trips, and his quest to visit every UNESCO World Heritage Site in the world, can be followed on his blog, Live Limitless.

A long-time addict of traveling, Matt’s first long-haul trip was back in 2009. Since then, he’s used travel hacking techniques to collect hundreds of thousands of frequent flyer miles, while helping many other Canadians do the same at Canadian Free Flyers. These miles have enabled Matt to (among other things):

  • Take his parents on a trip to Mexico city
  • Fly business class around the world. This included flights from Calgary to London, then on to Istanbul and Tanzania (with stopovers in Ethiopia and Japan) for just $750 in taxes. This trip alone is worth more than $15,000 CAD
  • Book an upcoming diving trip Indonesia, including a free, one-week stopover in Macronesia. After this, a visit to Mexio and Brazil is on the cards.
  • Book a six-month jaunt to Europe, Turkey, and India. This will see Matt and his wife, Carla, fly home First Class with Emirates. In travel hacking, this is as good as it gets. And it only cost Matt $80 in taxes.

Chris Guillebeau

Chris Guillebeau — photo on the right — is a renowned blogger, bestselling author, public speaker, and the mind behind the ever-popular World Domination Summit. On top of his many other commitments, he also runs the successful Travel Hacking Cartel: a site that shares travel hacking deals with its many world-wide members.

During the past 10 years, Chris’ Travel Hacking strategies have seen him visit every country in the world before the age of 35. The first 100 of the 193 countries visited cost Chris less than $30,000, all in. His overall savings from choosing to travel hack have totalled more than $150,000 USD.

It’s clear that “Travel Hacking” has a lot to offer. but what exactly is it? What does it involve?

How Does Travel Hacking Work?

Travel Hackers 2


Travel hacking in its simplest form is, says Guillebeau,

“[…] using air miles, points, and other creative strategies to see the world for less, and to have experiences that are normally cost prohibitive”.

Bailey agrees, pointing toward the “purest form” of travel hacking as using “the frequent flyer industry to your advantage”, along with “anything [else] that makes travel more accessible”.

In short, for many years now, companies have been offering rewards to their customers for doing certain things. Often these rewards come in the form of air miles or frequent flyer points. Once earned, these miles/points are credited to your frequent flyer account.

Travel hackers search high and low for these offers, and do what’s needed to top up their frequent flyer account. When there’s enough points in those accounts, they can be redeemed for luxury air travel, free flights, or discounted travel experiences.


Bailey explains that there are plenty of small rewards on offer such as “earning 500 points for liking a Facebook page, and big promotions like a new credit card with a 60,000 bonus upon signup”.

Other times, you may choose to “stay in hotels during promotional periods” or “transfer your points between reward programs”, all in the spirit of increasing the points/miles in your account(s).

Can It Really Offer That Much?

Travel Hackers 3

In a word, yes. Aside from the incredible experiences that both Guillebeau and Bailey have amassed, there’s an entire online movement that’s using the same techniques to great effect.


A quick visit to FlyerTalk, the top forum for travel hackers, will show you what I mean. With over 600,000 members, the site is awash with jargon-filled talk such as that below. But given a bit of time, Bailey assures me that it’s not too hard to get to grips with.

“Outbound: 7500 Krisflyer miles, SGD50 promotion, SQ Y, A333, DPS-SIN” (FlyerTalk Discussion)

In fact, Guillebeau only spends around “10 hours per month on [travel hacking], which is a lot for the average person”. Much of this time, he says, is spent geeking out on airline schedules, and maintaining a dozen different mileage accounts.

“But the greater point is that the average person doesn’t need to earn a million miles per year, like I do. Even with 10% of that, they can do a ton”.

If you’re prepared to put in even more time than Guillebeau, the sky’s the limit (excuse the pun). Take 25-year-old, digital nomad Life on the Road: The History of Digital Nomadism Read More Ben Schlappig for instance. As described by Ben Wofford in Rolling Stone: last year, Schlappig “walked into the Seattle airport and took the next flight to anywhere — and he hasn’t come down since”. For months now, Schlappig has been using his elite status with various airlines, and hotel companies, to take flight after flight, and the occasional hotel room, foregoing any permanent place to rest his head.

He manages this with an intense compulsion to find the hottest deals and undiscovered loopholes to take advantage of. This (along with a couple of related paid-for services on offer), has become Schlappig’s full time job.

How Bailey and Guillebeau tackle travel hacking, in light of Schlappig’s approach, may be seen as “moderate”. But this moderate approach is nothing to turn one’s nose up at. Their skills and accomplishments in this industry have taken years to hone. There’s a reason why people pay them both to help them into this game. They are living proof that these techniques work.

These are techniques that offer both of these guys an incredible amount of freedom and the ability to, as Bailey says, “get three trips for the price of one”. To travel to places that would otherwise be out of reach. And to do it consistently, month in, month out.

Get Started with Travel Hacking

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During our chat, Bailey shared with me tons of tips and advice for the beginner travel hacker. If you’re tempted to dip your toe into the warm, alluring waters of travel hacking, you’ll be well-advised to follow his lead. As Guillebeau maintains “the average newcomer is simply overwhelmed with information and doesn’t know what to do first, second, or third”.

The advice below will hopefully set you in the right direction.

Advice #1. First off, knowing where you can find reliable, timely information on the best deals to take advantage of is a must. Spend a few days poring over some discussions and articles over on FlyerTalk. Then, keep up to date with industry news by following blogs such as The Points Guy and View From The Wing.

Advice #2. Consider joining a relevant membership site such as Bailey’s Canadian Free Flyers, or Guillebeau’s Travel Hacking Cartel. Both of these membership sites offer step by step tutorials, and advice on getting started. They also offer real-time updates on new deals that you can take advantage of to top up your frequent flyer account. And they both have fantastic guarantees to ensure you succeed in your travel hacking endeavors.

Advice #3. Once you start to understand some of the more technical terms, and begin to see how the different frequent flyer programs work, you need to figure out what you want to achieve.

Do you want to go on a round-the-world trip? Do you want to fly around the Caribbean? Do you want to visit Europe? Your travel ambitions will largely dictate the frequent flyer program(s) you choose to join.

Screen Shot 2015-08-31 at 16.08.54

Research the major programs out there. Then, see which ones have partner airlines that will help you get to where you want to go. Working on collecting points for just one or two programs will be much more manageable than trying to collect points on all of them, so choose wisely.

Often, each program will allow you to use your miles not just on the major airline that runs the points program, but also on smaller, partner airlines. So if you choose to collect British Airways Avios points, you can also use these points to fly with Iberia, Monarch, and Air Malta, among others. Bailey explains:

Aeroplan is the reward system for Air Canada. For Canadians, this is by-far the best loyalty program to use. Other popular options include Alaska Airlines Mileage Plan, United MileagePlus, American Airlines’ AAdvantage and Delta SkyMiles. Then there’s Avios, Cathay Pacific Asia Miles and Singapore KrisFlyer.”

Once you’re following the relevant industry news, and are able to tackle some of the smaller “tasks” to earn a few points, you’ll want to start working toward some big wins. In travel hacking, these big-wins are almost always related to credit cards. Often, the more you do spend, the more points you receive, but the point is not to spend more than you normally would. The point is to choose the best credit card for yourself.

Screen Shot 2015-08-31 at 16.11.44

“I would say that you need at least one quality travel credit card. This means finding one that hopefully waives the first year fee but that also comes with bonus points. It should also earn at-least 1 point per dollar and the points should either be transferrable (such as AMEX) or be affiliated with an airline reward system that you want to use.

The more you spend, the more points you would have but I would never advise to buy things you don’t need. The balance has to be paid off every month. Otherwise, the points become devalued.

I don’t spend heaps of money but I do apply for many different credit cards at a time to get as many bonus points as I can. When it comes to groceries and gas and other everyday spending, I put it all on the cards.” (Bailey)

By following the sites mentioned above, you’ll hear about credit cards you can apply for, and any conditions you need to fulfill to earn those bonus points.

As time goes on, and you follow the relevant hints, tips, and suggestions on those sites, you’ll see your points balance increasing. Those points will increase even faster if you begin make your purchases either on your credit card, or through stores that are affiliated with that program.

For example: You can see stores affiliated with the AAdvantage program here.

Redeeming Your Rewards

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Once you’ve amassed a decent number of miles in your account, by signing up for various credit cards (without getting into debt) etc., you can then redeem these for flights, hotel stays or experiences. Usually, you’ll find the biggest savings in long-haul, Business Class, or First Class flights.

“[Redeeming points is] actually quite simple. Depending on the loyalty program of choice, you can usually just login to your account, search for flights and book online with points. If you’re desired itinerary isn’t available online, you can call in and pay a fee of approximately $25 to have the agent do it.

There are also professional services that do this for $75 – $150 per booking if you’re going after extremely difficult itineraries”. (Bailey)

Once you start becoming a more seasoned travel hacker, there are, of course, additional things you’ll learn to look out for. For example, if there’s a seat sale on the destination you’re visiting, it’s better to pay cash, and use the points for a later, more expensive flight.

Similarly, if you can find the flight for a decent price 5 Rules to Finding Cheap Airline Flight Tickets Who says you can’t fly for cheap? Sometimes it comes down to whether or not you click the right links, search the right terms, or pick the right times to search the web. Read More anyway (using sites like SkyScanner, Kayak and AirfareWatchdog), you should save your points for a later date.

As you can see, there are plenty of nuances to travel hacking. Enough to write several books on, in fact. But the basics are relatively simple.

  1. Find a frequent flyer program that works for you.
  2. Then find creative ways to earn points on that frequent flyer program.
  3. Redeem those points sensibly.

The sites mentioned throughout this article are all updated regularly, and we’ve been assured are all trustworthy. If you’re inclined to take advantage of these offers in your spare time (just a few hours per month is needed), these are all great places to start, and should, with some persistence, save you a healthy amount of cash.

Mix this with some Android apps to help you save money while on holiday, Save Money on Your Next Vacation with These Android Apps Summer is right around the corner, so you these Android apps to get a cheap vacation for you and your family. Read More  and tips on saving on your next vacation package How to Save Money on Your Next Vacation Package We all need a proper vacation now and then. If a holiday is on your horizon, you consider booking a vacation package. Here are some options. Read More , and you’ll be living the adventurous life Follow 10 Inspirational People & Their Personal Journeys Online They are not swashbucklers or cut from the silver screen cloth. They are normal everyday people who live extraordinary lives and in the process inspire us to never give up on our dreams. Read More in no time.

Is travel hacking something you would consider trying out? Where would you choose to fly using these techniques? And, do you think it’s worth it overall?

Image Credits: flying white model airplane via Shutterstock, A Globe by Mark Doliner (Flickr), Credit Cards by Got Credit (Flickr).  courtesy of Matt Bailey (Candaian Free Flyers) and Chris guillebeau (Travel Hacking Cartel)

Related topics: Save Money, Travel.

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  1. Matthew Bailey
    February 16, 2016 at 12:39 am

    Hey everyone!

    Just thought I'd chime in here now that I'm back from Micronesia.

    Travel hacking is not just for people looking to leave for 6 months or more. Some of my trips have been only a couple of weeks and I've also used it to bring my parents to Mexico, which was only a 10-day holiday. In that specific scenario, I got them a return flight to Mexico with a free stopover in Las Vegas for three nights. This trip not only saved $1000 on the tickets but also came with a "Free trip". You can't do this with normal discounted airline tickets.

    Secondly, I don't spend heaps of money. In fact, I'm probably one of the "poorest" Canadians around. For the moment anyways. I just spend my normal amount of gas and groceries and other expenses on the credit cards. Just this alone should amount to around 25,000 points per year (About $12K in spending) and cards usually come with a minimum 25,000 bonus points. In total, 50,000 points can get you a return trip anywhere in North America, Hawaii and most parts of South American and the Caribbean. Not a bad deal!

    Hope this helps!


  2. Anonymous
    September 15, 2015 at 2:55 pm

    These tips are great, and they do work. Often without spending any more money than you're currently spending. It's just switching payment methods all the time. The time it takes is far more than what most of these guys are reporting.

    Also, how are they making an income? The article doesn't address it - you can't vacation for 6 months at 30 years old without some type of income. What are the other parts of these people's lives? That's what we're curious about.

    • Rob Nightingale
      September 21, 2015 at 6:25 am

      Sure, these guys have their own income. As mentioned in the article, Chris is a best selling author. Both also run their own online businesses. They have both built a life that enables almost unlimited travel. I have also done the same thing, but haven't got into travel hacking all that much, but do find it fascinating.

      This is still possible for people working 40 hours per week in a cubicle, though. Everyone gets some holiday time, even if it's just a single week. Travel hacking could help to make this single week a once in a lifetime trip without the disporportionate rise in expenditure that would usually require.

  3. Anonymous
    September 14, 2015 at 11:50 pm

    This would work if one had the vacation time for all those trips. I only have two weeks a year and a mortgage, which is really limiting. That said, rather than using frequent user credit cards, I use cash back reward cards to defray expenses.

    • Rob Nightingale
      September 21, 2015 at 6:21 am

      Unfortunately, travel hacking isn't for everyone, though by collecting enough points, you could still help to make sure those two weeks off are incredible- upgrades to business class, or to hotel suites instead of rooms. Or simply to save some cash when booking that long-awaited holiday...

  4. Anonymous
    September 13, 2015 at 6:58 pm

    What if I use my Amazon, Paypal, and Amex points to pay for things I need, and use the savings to pay for vacations? That would give me the flexibility to use that cash saved on more pressing matters that might pop up (Like when our septic system failed!) Is it still worth perusing these blogs for savings if I don't have any airline miles?

    • Rob Nightingale
      September 21, 2015 at 6:20 am

      Everyone starts off without any airmiles, but travel hacking is predominantly centered around building your airmiles accounts. If you're someone who loves to travel, usually the savings you can make by utilizing your points for travel rewards, instead of material rewards, is financially much greater. It's all about learning where to spend your miles to get the best return...

  5. Anonymous
    September 12, 2015 at 3:17 pm

    I often find the titles of the articles on these kind of sites a little misleading. A lot of it is how to save money travelling if you can afford to travel anyway; rather than how to get to places you are struggling to afford to visit.

    For example, frequently spending is just moved into a different budget. If I spend loads of money generally then switching that spending to a card with air miles will reduce the cost of flying. On the other hand, a lot of places give discounts for cash so I could just do that and use the 'saved' money to buy the air tickets.

    • Rob Nightingale
      September 21, 2015 at 6:19 am

      Generally, from what I've seen, the savings from travel hacking are oftentimes greater than could be found by following through with alternatives. As you get futher into the rabbit hole of travel hacking, you can work on finding deals which result in "Manufactured Spending" (i.e. being able to spend on your credit card, earn TONS of miles, and then pay off the credit card, without being even 1c down. This is hard to do, and is quite complicated, but can save people a small fortune in travel costs...

      As mentioned, this article covers the very basics. There's also an entire rabbit hole you can delve into...