The Pros and Cons of Travel Hacking – My Experience

The Pros and Cons of Travel Hacking

Over the past couple of years, I’ve been dabbling in the world of travel hacking.

Travel hacking is essentially the process of signing up for a new credit card, spending enough to earn the sign-up bonus, using the points you earn to book free travel, and basically repeating that process over and over again.

If you’re using the credit cards responsibly and only spending what you would already spend otherwise, it can be a great way to quickly earn a lot points because the sign-up bonuses are much bigger than you would typically get from regular cash back offers.

Last year I wrote about how I travel hacked my way to free flights home for Christmas for my whole family, and since then I’ve done the same thing for a number of other trips.

So it’s been great, but there have been downsides too. Especially recently as I’ve run out of easy deals and it’s gotten more complicated and time-consuming to figure out my next move.

And since I’ve been asked about this by a lot of people who are intrigued by the idea of free travel, I figured that an honest assessment of my experience would be helpful.

So here are the pros and cons of travel hacking, based on my two years of trying it out.

The pros

The biggest benefit has (obviously) been all the free travel we’ve been able to get.

It hasn’t been anything fancy, but we’ve used our points for a number of trips that would have cost us some decent money, but ended up being basically free (you usually end up having to pay like $5 per flight in fees):

  • Multiple flights to and from Boston to see my family.
  • A family wedding in Chicago. This included one free night at our hotel.
  • A flight for me to spend a weekend with my college friends.
  • A flight to DC for a funeral.
  • A couple of flights for business conferences.

Basically, all the points we’ve earned have made it easier for us to stay connected with people we care about who live in other parts of the country. That’s been awesome.

The other big pro is that it was easy to get started and find big opportunities to earn points quickly.

We already used credit cards for all our spending, so there wasn’t any change in behavior needed there.

And when you’re starting from scratch, it’s easy to find good deals.

We started with the Chase Sapphire Preferred and Southwest credit cards, each of which earned us a lot of points that could be used cheaply for the flights we wanted.

The best choices for you might be different depending on where live and where you want to go. My friend Brad runs a great site to help you get started.

So the bottom line is this: if you’re already using credit cards responsibly, it should be pretty easy to earn yourself some free flights quickly.

The cons

The biggest drawback so far is that after about a year and a half, the easy opportunities dried up.

We’d already gotten the bonuses for the cards I mentioned above, along with a few others, and it wasn’t really clear to me what our next steps should be.

I ended up spending way more time researching our options than I should have. And as I’ve moved from one card to the next, it’s all gotten more confusing and time-consuming to keep track of.

And recently I got a couple cards that earned us a lot of points, but it turned out those points were harder to use than I thought they would be.

For example, we’re flying back to Boston in a week and it’s the first time in a couple of years that we’ve had to pay for flights. We were still able to book most of the trip for free, but because I wasn’t able to use our newer points like I thought I would, it ended up costing us a few hundred dollars.

I’m certainly not complaining about traveling on the cheap. I’m just pointing out that after the initial push it’s become much harder to find the path to free flights.

In other words, travel hacking is not a never-ending gravy train. At least not without significant effort.

There have also been a few times where I’ve caught myself being excited about spending money because it meant we were getting closer to hitting our sign-up bonuses. Not a good sign. Those bonuses are absolutely not worth it if you’re spending more than you would have otherwise to get them.

Have I actually spent more money than I should have because of the allure of sign-up bonuses? I’m not sure to be honest. But it’s something I worry about.

The upshot? I’m still doing it, but…

Even though it’s gotten more difficult as I’ve gone along, I’m going to keep travel hacking.

The bottom line is that travel is important to us, especially to see family, and travel hacking makes it a lot more affordable.

But, I’m going to be more laid back with it than I have been recently.

When I started this travel hacking experiment, I got it in my head that we could travel for free forever. Now I know that while that’s probably true, it would take a LOT of time and effort. And to be honest, I’d rather spend that time and effort elsewhere.

So no more spending multiple hours researching the next credit card. No more trying to figure out all the intricate details of how different frequent flyer programs work and how to maximize every little thing.

Instead, I’m going to stick with the small number of moves that will have a big impact without requiring a ton of time researching how they work.

We’ll still get a lot of free travel. And it will come with minimal stress and more time for things that I not only care about, but that will have a bigger impact on my bottom line.

What’s your experience with travel hacking been like? Any tips or tricks for people who are still learning to do it right?

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2 Comments... Read them below or add one of your own
  • Michelle December 8, 2015

    I love love LOVE travel hacking! I churn around one card every few months and it’s like free money.

    • Matt Becker December 8, 2015

      I’m glad it’s working out so well for you! I’ve definitely enjoyed the free money as well.

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