49,472 Reasons to Try Travel Hacking

Go away often!

Go away often!

Yearning to visit a bucket list destination, but held back by the exorbitant price tag? Travel hacking might be just the ticket. This new art/science allows even not-so-frequent flyers to earn valuable travel perks - without investing a lot of time, resorting to nefarious means, or risking their creditworthiness.

Travel hacking is the practice of optimizing rewards to earn free travel.  At first blush, that might invoke off-putting memories of the quagmire of complex algorithms and blackout dates of old. But don’t take off just yet!

These days, travel vendors have beefed up and simplified rewards programs. They’ve teamed up with partners to enhance benefits. And the Internet happened. These developments gave rise to a new breed, travel hackers, whose money-saving tips can add up to a bundle.

I Believe I Can Fly

Chances are your travel patterns have evolved in parallel. Indeed, that’s what started me on this journey. Historically neither a frequent nor loyal enough flyer, I’ve left a trail of expired miles across multiple accounts.

But with a recent move 3000 miles from family and an ever-expanding bucket list, the time had come to proactively pursue frequent flyer miles. In my experience, Southwest is the worst form of air travel “except for all those other forms that have been tried from time to time.” Although I LUV them less than I used to, I still fly them most, so that was my first stop.

With 40,000 points for cardholders who spend $1000 in the first 3 months (piece of cake!), the Chase Southwest Rapid Rewards VISA seemed like a good deal.  The card fared well with the travel credit card rating tool from financial blogger Mad Fientist. Research revealed other expert travel hackers agreed, so I was cleared for takeoff.

Applying online meant resurrecting my long-neglected Rapid Rewards account. Logging in, I expected to see a large balance from 5+ recent flights, but my total was exactly 0 points!  I’d assumed Southwest would automatically associate the trips with my account, but you know what happens when you assume. Although my pleas to recover all the points fell on deaf ears, I did emerge with 9,471 points. 

One Last Point

More attentive readers may have noticed that something doesn’t quite add up here.  So far, I’ve given you only 49,471 reasons (about 1.5 trips east) to travel hack, one short of the promised total. The final one, peace of mind, came to the fore in March when I lost my beloved great aunt suddenly. 

There was no question that I would return to New England to say goodbye alongside family.  The question was “At what cost?”, given the premium for last minute travel. Going forward, I’m looking to travel hacking to take that worry off my radar screen.

Get Onboard

If 49,472 reasons are enough to make you want to go away often, where do you begin? A Google search for “best travel hackers” returns 2.5 million hits!  Having completed only the first step of A 60-Second Guide to Travel Hacking, I’m in no position to judge their merit. As a CFP® prone to taking a conservative tack with things that appear too good to be true, I probably never will be.

 But in my year as a personal finance blogger, I’ve come across several people whose work stands out for its integrity and no-nonsense approach. If I ever exhaust the ideas in the 60-second guide, these will be the next stops on my journey:

 Fasten Your Seatbelt

Travel hacking is not without pitfalls, and it’s not for everybody. As the cautionary tale of my lost points suggests, inattention to detail can cost you.  It’s also possible to waste a lot of time. Those are the most innocuous of the bad outcomes.

At the extreme, the twin temptations of overspending and credit card flipping can lead to a slippery slope of late fees, high interest rates, and plummeting credit scores.  Worst case, you find yourself in a debt spiral that leads to financial ruin, all because you “needed the miles.”  Now there’s a trip nobody wants to go on! 

In the end, it turns out travel hacking is a lot like financial planning. You identify your goals, risk capacity, and risk tolerance; craft an initial plan; make course corrections over time. If you approach it this way, I bet you’ll find way more than 49,472 reasons to take a flyer on travel hacking.