Let's Go, Jane!

I learned about “travel hacking” about five months ago, when I realized that my desire to see the world and my current financial picture were at odds with each other. Travel hacking, also known as “points and miles,” is the practice of opening new credit cards with sign-up bonuses and using your regular spending habits to meet the minimum requirement, paying them off in full at the end of each month. Once a bonus is achieved, you can move on to the next card. When done responsibly, it can be an amazing way to unlock international adventures on a shoestring budget.

The learning curve for how to earn points was not too bad. My favorite resources are 10xTravel and The Points Guy. What is FAR more difficult is learning how to redeem points. After clearing a few bonuses, I ended up with a mix of airline-specific miles, transferrable points from AMEX, Capital One, and Chase, and a vague idea of how the three airline alliances and transfer partners work.

As I believe all good trips begin with a spreadsheet (not joking), I made myself a list of all the airlines that accept my transfer points and started running searches. I immediately got overwhelmed by all of the variables. The dates, the starting location (I have five airports within an hour of me, not to mention the option of “repositioning” to another city), and the final destination. I needed to narrow my search WAY down if I was going to book my first award flight.

Award travel is best done in one-way tickets booked directly with the airlines. The alliances mean that you can book a British Airways flight through American Airlines, or a TAP Air Portugal flight through Air Canada, etc. It’s enough to make your head spin.

I settled on Madrid as my first destination because I love the food, and I have 8 years of classroom Spanish collecting dust in the darkest recesses of my brain. Grad school is about to start up again in a couple weeks, so I chose New Year’s as the next time I can manage a 5-day trip.

It took a LOT of trial and error, but I finally found a great one-way nonstop fare on United Airlines flying out of Newark, NJ. I had to wait several weeks to book it because I’m in the process of changing my last name after getting divorced. While United made the name change right away, Chase had to send me a paper form in the mail (or by carrier pigeon, those were the only options). Once my name matched in both places I could transfer the points, and luckily the flight was still available. I found a return flight on Iberia Airlines flying back into JFK airport for a combination of points and cash.

All told, my round-trip ticket to Madrid for New Year’s cost me $126 (and 58,100 points). While there is certainly room for improvement, I feel like my first redemption was a success. Now I just need to figure out where to stay. Luckily, there are dozens of great options on Airbnb and some interesting hotels to check out. That is what I will tackle next.

I can practically already taste the tapas. ¡Buen provecho!