August 11, 2022

What Is Travel Hacking And How Do I Start?

Over the last decade, travel hacking has become a mainstream phenomenon, largely thanks to social…

What Is Travel Hacking And How Do I Start?

Over the last decade, travel hacking has become a mainstream phenomenon, largely thanks to social media. Influencers show off exotic destinations on Instagram, reached by clever use of rewards. And the appeal is widespread. Families can significantly bring down the cost of a Disney vacation, while the aspirational crowd can book first-class tickets for pennies on the dollar.

As someone who has been travel hacking for over a decade, I’ve seen and done it all. It’s a rewarding hobby that can open up a world of travel opportunities. What is travel hacking, exactly? It’s a series of methods used to earn points (often without flying or staying at hotels) and redeem them for travel. By hacking flights and hotels, you can save substantially on these expenses.

How to start travel hacking

If all of that sounds exciting and you’re eager to get going, here is the quickest path to get started with travel hacking:

Set a goal

The first step in your travel hacking journey is to set a travel goal. Earning points without knowing what you’re using them for can be an exercise in futility. When I started back in 2011, I made the mistake of mainly accruing Delta SkyMiles and American AAdvantage miles for a trip to Europe. I learned pretty late that American Airlines had a weak route network to Europe and that United miles would have been a much better option back then.

Think about where you want to go (well before you start earning points) and research the best rewards programs to get you there.

Get a good rewards credit card

The easiest way to boost your points balance is with a rewards credit card. You can typically earn 50,000 or more points after completing a spending requirement over three or more months. While welcome bonuses are a significant draw, you can also take advantage of category bonuses and annual spending bonuses to maximize everyday spending.

Most people will benefit from credit cards that earn transferable rewards like these:

These currencies offer the most flexibility because you can transfer them to several airlines or hotel programs at a 1:1 ratio. If one transfer airline doesn’t have award space on your desired travel dates, then you can transfer them to one that does. It gives you options and protects you against possible program devaluations.

Once you have a general sense of which credit cards to apply for, make sure you’re ready to score them by:

  • Having good credit. As you might expect, the best travel rewards cards require good credit. To incorporate credit cards into your travel hacking strategy, you’ll need a score of at least 700. Hopefully, you’re already there or working on it.
  • Knowing the application rules. Every bank has its own rules pertaining to credit card approvals. Chase has the infamous 5/24 rule that restricts welcome bonuses if you’ve applied for five or more credit cards in the last 24 months. Amex’s once-per-lifetime restriction means if you’ve earned a welcome bonus for one card, you likely won’t be approved for another. There are many more credit card application rules to be aware of. Knowing them before you hit “apply” improves your chances of being approved for a travel rewards credit card.
  • Paying your balance off every month. If you struggle with paying your credit cards off every month, travel hacking with credit cards is probably not for you. That’s because the interest rates on these credit cards are high and will negate any rewards you earn. If you’re not confident you can pay off your balances, you’re better off skipping the credit cards and using alternate methods to earn points and miles.

Use shopping portals

Shopping portals are the way to go if you want to add another tool to your travel hacking repertoire. Nearly every major loyalty program has a shopping portal you can earn rewards with. You’ll earn at least one extra point per dollar spent, plus the points from your credit card.

The easiest way to ensure you’re earning the most points possible is to use a shopping portal aggregator like Cashback Monitor. Type the name of an online merchant and you’ll get a list of shopping portals alongside their earn rates.

Many shopping portals also offer spend-based bonuses around the holidays and right before the school year starts. These can be pretty lucrative, helping you reach your travel goals faster.

Sign up for dining rewards

Dining reward programs are similar to shopping portals in that they require minimal effort to earn extra points. You can join one of seven airline and three hotel-affiliated dining programs to earn up to 8 additional points per dollar spent.

These programs even offer first-dine bonuses and extra points when you write reviews or meet certain spending thresholds every year. They provide elite status for frequent diners, with elevated earning rates.

You can join all of these programs, but since they’re all part of the same network, you can’t register the same credit card with more than one program at a time. That shouldn’t be too challenging, even if you only have one credit card. Simply register your card with the program of your choice, earn the first-dine bonus and repeat with the other nine programs until you’ve earned them all. Don’t forget to use a credit card that earns bonus points on dining to maximize your earnings.

Get creative with earning miles

Once you’ve gotten into the habit of maximizing your everyday purchases, it’s time to get creative. What else can you charge to your credit card? I once convinced my boss to let me pay a $35,000 supplier invoice with my credit card. I’ve earned thousands of points on rent and mortgage payments through Plastiq. I’ve used retail arbitrage to flip dresses worn by Kate Middleton and earn spending requirements.

Think outside the box and you could be well on your way to discovering new ways to hack travel.

Learn the rules

Familiarizing yourself with award program rules is paramount to beeing a successful travel hacker. Knowing whether a program allows stopovers, one-way awards and other intricacies can help you piece an award ticket together when traditional methods fail.

What are the best travel hacks?

There are countless travel hacks out there and the best ones are top-secret (for good reason). But if you’re just getting started and want to keep things simple, here are the most valuable hacks to be aware of:

Card sign-up bonuses

Credit card sign-up bonuses are by far the best travel hack. You can piece together a luxury vacation by strategically applying for credit cards. It that can help you achieve your travel hacking goals faster.

Double (and triple) dipping

Double- or triple-dipping is one of the best travel hacks out there. Stacking travel hacking methods can help you earn significantly more miles. For example, let’s say you’re in the middle of a home renovation project—you’ve got expenses and they’re big. If you can do some shopping online, you can double-dip by earning rewards on your credit card and an online shopping portal.

If you happen to have an Amex card, you could triple dip by taking advantage of Amex Offers. I’ve managed to do this for large expenses like travel bookings and furniture purchases. Think about all the possible ways to earn points and find opportunities to combine them.

Mistake fares

There’s more to travel hacking than just earning and redeeming points. One of my favorite ways to hack travel is through mistake fares. Sometimes airlines mess up and publish fares well below market value. I’m talking about a $450 round-trip business class ticket to Shanghai or a $120 economy class ticket to Abu Dhabi. Over the years, there have been dozens of great mistake fares that travel hackers have taken advantage of.

In most cases, airlines have honored these mistake fares, which has been great for savvy travel hackers who managed to book them. A great way to stay on top of mistake fares is to sign up for alerts with Airfarewatchdog and The Flight Deal. These sites sparse the web for amazing deals and share them on social media and their websites when they come around.

Maximizing award redemptions

When you’re ready to book that dream vacation you’ve been saving for, there are three types of awards you should look into: Sweet spots, off-peak award charts and award sales. Sweet spots, in particular, can help you save significantly on award flights.

Many airlines and hotel chains offer peak and off-peak award pricing. By being flexible with your travel dates, you can stretch your hard-earned points further.

How can I travel for free?

Despite what travel influencers like to put into their photo captains, there’s no such thing as free travel. You will almost always pay a fee to earn or redeem points. Whether it’s your credit card annual fee, award flight taxes or resort fees, there will always be costs. But by leveraging credit cards, points and loyalty programs, you can book incredible travel experiences at a fraction of the cost.