Travel Hacking 101: Turning That Dream Trip Into Reality!

Before anything, we must define what exactly “travel hacking” is and most importantly, what it is not. Travel hacking certainly does not mean that you will have to become the next Edward Snowden, or join Anonymous, or even that the CIA will be knocking on your door for doing this! Although, maybe by the time that this post is over, the NSA will have flagged it down for the number of times it says the word “hacking.” So now that I have clarified that travel hacking doesn’t actually involve somehow finding an airline’s password, accessing their database, and adding your name to a first class seat, and hoping that they don’t realize what went down: what is travel hacking? Well, travel hacking just means you are taking advantage of all the resources you have to be able to book free/heavily discounted flights, accommodations, and more! Now, doesn’t that sound wonderful? That trip you’ve always dreamt of is closer than you think! So in this post, I’m gonna share a few tips and ideas to get you started on that next trip of yours!

Tip #1: Rewards/Loyalty Programs

United Airlines back in the 70s was the first airline to have a frequent flyer program, and needless to say, that was popular and led to many airlines and other industries to follow suit. So with that being said, you should definitely sign up for as many as airline and hotel programs as possible, I mean why not? They are free, and it lets you earn valuable points that will go towards any future travel plans you may have! Now, you certainly don’t have to do it now, right at this second, but every time you take a flight with X airline and/or stay at Y hotel chain, you should be crediting those to your reward program: message of all of this is don’t let those go to waste! If you are in the US, like me, I would suggest you have a membership account for at least the three biggest US airlines: American, Delta, and United. I picked these three in particular because each of them are in one of the three major airline alliances in the world: American is in OneWorld, Delta in SkyTeam, and United in Star Alliance. If you want to read more on what exactly alliances are, and how they benefit you, here’s a link to a pretty good article that explains it: https://thepointsguy.com/guide/airline-alliances/.

Now I know that if you are a frequent traveller, or if you’re just like me who just signed up to any rewards program I could think of right then and there on the spot, you must be wondering how you’ll be able to keep track of all of these. Well, Award Wallet just may be the answer for you, like it was for me! It keeps track of all your loyalty points in one place and it even notifies you whenever when your miles/points are about to expire! (and most importantly: it’s free!)

To wrap this section up, here’s the main take you should get from this: NEVER LET POINTS GO TO WASTE! Hope that’s clear enough, and that’s the #1 rule of travel hacking!

Tip #2: Be a Loyal Customer

Now, I am not going to spend a lot of time on this point, but it’s a surefire way for some people to accumulate points and miles to be able to get free or discounted travel. For example, if the airport that is closest to me (IAH) is a United hub, then maybe it makes sense for me to fly frequently with United, as they have a lot of options in terms of travel destinations and can get me there faster. If I lived near Dallas-Ft. Worth (DFW), it would make sense to regularly fly with American for the same reasons. Now this customer, in order to get enough miles and points for free travel, would have to be flying with the same airline and staying at the same hotel chain each and every time. Personally, I don’t think it’s practical because it’s not always the most cost-effective and may not have the best availability for what you are looking for! One scenario that this actually makes sense to be a loyal customer is if you are on a work/business trip. For example, my dad has to travel for work to Seattle every month, and every month he flies with Alaska Airlines. It makes sense for him to do so in this case since the company pays for his flight, so essentially he’s earning free Alaska miles every month. Unfortunately, not every trip you will be reimbursed for like in that example, so it doesn’t make sense for you to pay extra just to be able to fly with a certain company (or maybe it does for you, not judging). This idea leads into the next section, tip #3!

Tip #3: Shop Around for the Best Prices

More often than not, it is not rewarding both financially and for quality of service to stick to airline or a hotel chain. I will talk about this more in-depth in another post, but you should definitely look up “Bonvoyed” on Google as an extreme example of how some “loyalty” programs are not exactly the most consumer friendly. That’s why some companies like Expedia, Booking.com, and AirBNB have popped up in the last few years, to allow travelers to get better rates on flights, hotels, and everything travel-related. I won’t be spending too much time on these companies (and Google Flights), because many of you are aware of how these work, but I want to show you a few other resources that I actually either use or subscribe to in order to find the best deals and prices!

Travel Websites:

Matrix ITA

Matrix ITA Homepage.

Before there was Google Flights, there was Matrix ITA. This website is often one of my go-to’s, it lets you customize so much, and it is so easy to use! It looks a little intimidating at first, but trust me, it is super easy to use and get the most out of it! It quickly searches its databases and helps you choose the cheapest options available, helping you save time and money! There are a couple things to watch out for, though, as no system is truly perfect. First, the website does not allow for direct booking. You would find the information on the Matrix, then go to the airline’s website and book directly on there. If you are still using a travel agent, whenever you select the flights you want, it’ll show the “fare construction,” that way you can just send it to your agent and he/she is able to quickly look it up! Another drawback of this, but that’s nearly every site, is that some low-cost carriers like Southwest in the US or Ryanair and Easyjet in Europe don’t appear in the search. Finally, it is a little slower than Google Flights. But if you are looking for something straightforward and that allows you to customize your trip, then look no further than the Matrix!

Momondo/Skyscanner

Momondo’s homepage.
Skyscanner’s homepage.

These next two websites should have a familiar layout to many users, so I won’t spend too much time talking about them. They are another couple of websites to check out and make sure you are getting the best deal when shopping around for flights. Unlike with the Matrix, you can actually purchase directly from these websites, so if you are in a bit of a time crunch or just looking for something a little more convenient, these two websites are definitely ones to keep in mind!

Travel Subscriptions:

The Flight Deal:

A great way to stay informed of the latest deals or to just explore some destinations you could potentially travel to, The Flight Deal is a great resource to subscribe to! As you can see, they send out a free newsletter every day of the week and summarize the best deals that they found on that day. It’s a great way to plan ahead, or just simply find new destinations to travel to that just happen to be at a decent price. These deals are usually for international travel, but if you see “The Shorthaul” they are usually domestic flights (within the US, of course). Apparently they now have a subscription service (or maybe they’ve always had it), where you can get “real-time deals,” but honestly the free daily newsletter is usually plenty of information as it is! The other day, they found a $22 round-trip flight to Puerto Rico from Boston with JetBlue, unfortunately that fare is now long gone!

Scott’s Cheap Flights:

Scott’s Cheap Flights Deal of the Day!

Much like “The Flight Deal,” you can subscribe to SCF and get the day’s best deal, maybe it just so happens that the destination you want to go to is having a great sale, or it inspires you go to somewhere like Iceland, which was having a great sale recently. Currently, all the deals being sent out daily by SCF are for at least 3-4 months from now, so you’ll be ready to go whenever we are allowed to resume traveling! The main difference between these two websites is that in the free version of SCF you only get one curated deal of the day, whereas with The Flight Deal sends out numerous deals each and every day. The reason that you only get one deal with SCF is that they have a subscription service, which costs about $49 and gives you access to their entire list of daily curated deals. I am not a member of this service, but you can certainly check it out and see on their website on what you would be getting by paying about $50/year!

Tip #4: Fifth-Freedom Flights

Onboard a Singapore Airlines A350: Houston to Manchester.

First and foremost, thank you for reading up to this point! If you’re reading this far, you must be really serious about your travel or extremely bored at home during this quarantine, but either way: THANK YOU! Now, if you haven’t come across this term before, you must be wondering: what in the HECK is a fifth-freedom flight? Well, it’s unfortunately not a flight with a screeching bald eagle that represents freedom. It’s also not a flight with a bunch of terrible jokes by the author, which you may be glad about! A fifth-freedom flight just means that it’s a flight operated by an airline whose base of operations is in neither the origin country nor the destination country. For example, Singapore Airlines has a non-stop flight from Houston to Manchester. Or Emirates has a New York-JFK to Milan flight. In both cases, these “random” flights are a connection en route to that carrier’s home. After leaving Manchester, Singapore Airlines flies, you guessed it, to Singapore. Same with Emirates, it flies from Milan directly to Dubai. These are just two examples of the many fifth-freedom flights that currently exist, if you want a bigger list for North America, click here.

Now that we talked about what exactly fifth-freedom flights are, why do they matter? Well let’s take this scenario above. I am looking for a one-way ticket to London on August 4th from Houston (IAH), which is the closest international airport to me. IAH is a large United hub, so that’s why I pulled up a United search, and the price came out to $1,794 for a 9-hour, non-stop flight to London-Heathrow. To compare, I also searched on Singapore Airlines’ website for a flight on the same day (August 4th). Let’s take a look at how the two compare:

Taking a look, it should immediately stand out to you the price difference. Flying with Singapore to Manchester would only cost you $465, that’s saving you $1,329!!! But how would you get from Manchester to London? Well, trains run from Manchester to London daily and cost about $30 in the off-peak one way, or you can fly British Airways, with prices ranging from about $60-80 one-way to London- Heathrow. So even if you paid $80 for a flight to London, you’d still be saving $1,249! That’s $1,200 that can go towards anything else from lodging to sightseeing to maybe even turning it into a longer vacation! That’s why these fifth-freedom flights matter! Not only are you saving, but you also get to have an experience on an airline like Singapore (who was voted 2019’s 2nd Best Airline in the World by Skytrax) without having to go all the way to Singapore.

Of course, there are some things to be aware of with booking these fifth-freedom flights. First, they are not always cheaper, they can be a great alternative to the big US airlines, but for example, I found a Westjet flight on the Matrix that was $20 cheaper. But then it comes down to preference on if that fifth-freedom flight would be worth for the experience! Second, they do not run every day, it may change from season-to-season. At times during the year they could be running at a different frequency, so it’s always important to check.

Closing Thoughts

If you have taken the time to read some of the tips that I have laid out in this post, I hope that you have learned at least something new today. Travel hacking can be done by just anyone, trust me, sitting here a year ago, I knew none of this stuff. I accidentally came across a fifth-freedom flight last year and didn’t even know why/how it existed! You don’t need fingerprint scans or any secret passwords to be able to travel for free or at least more affordably. If there is anything that you should take away from this post is that you should never let points go to waste, each and every point is valuable when it comes to your travel goals. By no means, is this a comprehensive guide, believe it or not! For example, if you know me personally, you must be asking yourself: did he really just go an entire post without talking about credit cards? Where are all the credit card points that he talks about? Is this really him writing this post?

Well, don’t worry it is still me! I’m still here, credit cards and all, but credit cards deserve a post of their own, maybe multiple posts of their own. This post was meant to be an introduction, to ease you into this and give a couple of tips to add on a couple of things to what you may have already been doing. This would be the slow and steady approach to travel hacking. Credit cards are a game changer, they can drastically improve both your travel quantity and quality. But that’s for next time! Let me know what you think about this post! What are some of your go-to websites for traveling? How do you plan your trips? Have you used any of the resources listed before reading this article?