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Flight Travel Hacking 101: Finding Cheap Flights…For Beginners

Flight Travel Hacking 101: Finding Cheap Flights…For Beginners

This is literally for the newbies out there. You know that there are better ways of finding cheap flights but you haven’t had the time to dig in and do the research. Don’t worry, these quick steps will get you started straight away on your path to flight travel hacking master status!

It’s a 101, so it’s surface level, uncovering the top of the dark depths of the rabbit hole, enticing you to dig deeper. And it’s a wicked deep hole my friend! Flight travel hacking gets really fun, and addicting, once you start digging in and getting the hang of it!

To any trolls out there, this is NOT a next level ninja flight hacking tip compendium. Please take your cranky and dish it out somewhere else. Hugs.

I’m a total nerd for research and trying to understand things. Spend about an hour reading this article and just testing the waters. It will likely open your world up and make finding cheap flights so much easier, even if you just use one or two tips. In no time you’ll have it down to an art!

Flight Travel Hacking 101: Finding Cheap Flights…For Beginners

Flight Travel Hacking 101: Join Many Frequent Flyer Programs

Sign up for at least the 5 major frequent flyer programs for major airlines in your region…like now. This is the bare minimum! You probably want to make sure you have accounts for more. In reality, your life is long, and you can earn a slow amount of points on all of these even if you’re not working the credit card bonuses. Don’t pass up free flights and perks!

Don’t worry, this should really only take you about 10-15 minutes, tops, since if you’re reading this you’re likely already a member of a few.

Here are a few from the top of the heap, in case you haven’t signed up for them: American, Delta, United, Southwest, Lufthansa

Reason: You’re going to be surprised to find that just because you live in a “hub city” doesn’t mean you should be swearing by that hub airline. So you’ll likely look at different carriers a lot more often from here on out! More on that later!

Finding Cheap Flights: Flight Search Engines and Flight Aggregators

DO NOT swear by one particular flight search engine! I was a HUGE dill hole for so long, only swearing by one or two major flight search engines. Unfortunately, that was usually because one particular engine had dumped a sh!tton of money into marketing!

I now usually use 2-3 at the start of a search, which really only takes a few minutes to narrow down. I start with finding the cheap days and airlines with something like Skyscanner or Orbitz or Google Flights, then I’ll jump to a combination of actual airline/carrier sites.

Go rogue and open a private browsing window so they can’t track your search habits and possibly change flight costs later!

You wouldn’t swear off all kinds of ice cream or relegate to one or two hot sex positions would you? Then why would you assume only one or two flight search engines is all you need!?

Reason: Different engines have different strengths and weaknesses! I’m not busting balls on any one particular. Just saying that they’re all beneficial for different reasons. You personally might like different interfaces that make finding cheap flights that much more easier or enjoyable for you.

Flight Travel Hacking 101: Don’t Forget The Airline Sites

I think that a lot of folks feel that the airline-specific sites (like aa.com, or united.com…) are the devil! For some reason, I always thought that buying through a search engine was the way to go.

Reason: If you’re in the frequent-flyer program, unfortunately, a lot of time you can’t get points attributed to your account if you use a discount site! No bueno for me! Also, if you’re using airline-specific credit cards, you’ll often get compounded points over and above for using that card when purchasing through their airline portal. Yes, sometimes the tickets are a couple of bucks more expensive, but you typically make a big win on the points side, and that’s the long-term play.

Flight Hacking Tip: Get the Airline Credit Card

Did you know that 50%+ of people keep their first credit card for years and years!? That’s just out of some flaccid idea of nostalgia or “loyalty”! They’re not even paying attention to whether they’re getting great perks!

Not gonna lie, I had my first for like 10 years! Once I started learning a little bit about flipping credit cards and getting massive mile bonuses, earning free flights became my new normal!

The only thing better than finding cheap flights is finding free flights!

Reason: Most credit cards that are connected to a certain carrier and their site give killer initial miles bonuses, upwards of 30-50k. Additionally, most offer a free checked bag or two when used, along with other perks. Even if there’s a yearly fee, you’re usually getting at least your money’s worth with a single flight in a year. Once you start working these bonuses you can get baller cheap flights or almost free flights like these!

Note: The key to credit cards is not carrying a balance! If you aren’t financially responsible or debt-free, or are not paying off every revolving account monthly, then don’t go getting in this game until you are!

Sign Up For Free Flight Alerts

Most flight search engines allow you to put in your email address and they’ll let you specify airports, regions, destinations, etc. Then they’ll send you catered emails with deals you might be interested in! Yes, I hate junk mail as much as the next person, but when that “junk mail” can introduce me to options that I’m not necessarily on the lookout for, I’m in. Guess it’s no longer junk mail!

Reason: Finding cheap flights in your sleep and waking up to an email laying the options out for you friggin’ rocks! These are really good opportunities to wanderlust a little too! You also start to passively learn which airports have the best deals for different regions. You’ll get better and better at flight travel hacking as that knowledge stacks up over time!

Don’t Swear By Round Trip Flights—One-Ways Are Your Friends

Yep. Somehow I think we’re led to believe that round-trips or even multi-point flights just make the most sense, but that’s just not always the case. This flight hacking tip is a little bit odd, since actually, most people don’t even realize that multi-point flights (city to city to city…) or stopovers are a thing! (I talk a little more about this at the end of the article.)

I was looking at a $7-800 flight from CLT to AUS to DEN and back. Looking at one-ways on different carriers changed that to just over $300. Boom goes the dynamite.

Reason: Because different airlines do have hubs between different cities, you might find it cheaper to take different 1-way flights to multiple airports if you’re doing a multi-city trip. Another thing to look for is which days are cheaper than others for different carriers. Flexibility here is key.

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Flight Hacking Tip: Pay To Play For Finding Cheap Flights

Many years ago a small business owner said some words that are music to a graphic designer’s ears: “You have so spend money to make money.” This actually had nothing to do with the fact that I was invoicing him! It had to do with the fact that I truly believe that spending smart money can pay huge dividends in the end!

This is actually a flight hacking tip that I don’t think people take that much advantage of. The problem is that it’s all about perspective. Spending $30-40 a year for an app or service that will literally have you saving upwards of $250-1000 per flight makes sense…even if you only use it once a year!

Finding cheap flights takes time! What is your time worth?!

Reason: Most of these services scour super deep and they’re really good at finding cheap flights and error fares. They’re ninjas at pinpointing specific airport or region “equations” that you personally won’t find, or don’t even know to look for.

As much fun as I feel flight travel hacking is, I’m happy to let someone else do the work for me! Check out apps/sites like Scott’s Cheap Flights (or so many others). Spend a little, get a lot.

carry on luggage travel hack travel tip

Go Carry-On Only And Get Creative: Skiplagged

I fly with only a carry-on backpack and a personal item for like 99% of my flights. Mostly because if you get bumped you can score big with free flight or credits—or lose big like I did here! I use the Tortuga Outbreaker series packs, which are friggin’ amazing. There’s a reason they’ve won tons of awards! Once I did that my options opened up quite a bit, and I really started cutting some corners.

FYI, this is next level stuff here, so it might take a bit for you to get this into your comfort zone.

The site Skiplagged is a great tool, and I often use it as my starting point for finding cheap flights and carriers in general. I love their little wavy line graphs and how simple they are to explore days and costs.

Skiplagged made its name on showing you the flights that actually have your personal final destination as the layover of a flight. Turns out, you can try all you want to find directs, but they may be way more expensive than getting a 2-3 point flight and just skipping the last destination! Note that you can’t check your bag, since that would make it end up at your final ticketed destination!

That might be a bit confusing. Essentially my first Skiplagged flight was coming home from Mexico.

The direct flight to Charlotte was well over $300, but a flight from Mexico City to Orlando with a stopover in Charlotte was less than $100!?

Since I was flying carry-on only, I took the bait. The worst thing that could happen was that I would end up in Orlando for a day or two, get another $100 flight home, and I’m still #winning! But all went well, I got off my “layover” in Charlotte and didn’t board my next flight. I just went home!

Note: This method clearly has a bit of risk, and I assume eventually the airlines might catch on. They may start charging people for dropping off a flight. But for the time being it’s a nice flight travel hacking workaround!

 Don’t Forget Travel Insurance

I would be remiss if I didn’t mention travel insurance. There are many companies out there to choose from and there are tons of different reasons why one insurance or the other might be right for your next trip. Personally, I don’t travel without at least travel medical insurance. Especially if you have a pre-existing condition like I do!

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OK. Hope that gets you started down the road! Let me know if you score a new flight or a big win by hitting up the conversation over on Facebook!

Cheers!

— Jason

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Travel Planning Tips

Figure out where you are going & how are you getting there…
I suggest using at least 2 to 3 different travel search sites. Start with Skyscanner or Orbitz or Booking …or whatever aggregator site you prefer. Then when you see what airlines to use, check their respective sites for better deals or rewards flights.

Figure out where you’re going to stay…
If you’re interested in hostels, search Hostelworld or Hostelling International. For longer-term or more private digs, look at Airbnb, VRBO, or you can look for hotel rooms in the links from the search engines listed above. 

Get comprehensive travel insurance, or in the least, travel medical insurance if internationally…
Especially with Covid not going anywhere, get covered. Start an insurance aggregator like Insure My Trip, or with SafetyWing, World Nomads, Travel Guard, or TravelEx. Then decide what is important to you; trip cancellation, baggage coverage, medical, or all of the above. 

Need more resources? Click here!

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