I’ve been reading about travel hacking since before I began this blog, but hadn’t put any of my knowledge into practice until about two weeks ago. And it’s all because of a mistake I made recently.

Too eager for a deal?

My plane tickets for Cents Positive showed up in September’s spending report; there were no good options, and I paid more for them than I was expecting to. My flight out to Denver was a $90 leg on Frontier^[*] and my flight back was $223 on Southwest.

Right after FinCon I checked my email and noticed that yet again Southwest was having a sale (it seems to happen quite regularly), so I decided for funsies to look up my Denver-DC flight. Lo and behold, it was now $17 cheaper than when I’d bought it!

My first travel hacking experience is actually flying on Southwest, period. Because getting to change your flights without cancellation/change fees is AMAZING. I am not honestly sure I ever flew Southwest prior to this year, mostly because my flight strategy is to fly the cheapest option that makes sense. I don’t have any loyalty to any particular airline, which is why I won’t be getting any kind of status anytime soon. That’s okay, since I don’t fly enough anyway to get status, even if I took the same airline every time. But earlier this year Southwest was my best option for a flight, and I wasn’t sad about that, given their generous cancellation policies. Not that I took advantage of them—until now.

A good idea in theory…

I didn’t see a $223 credit on my account when I went to rebook my flight, which meant that they’d refund my credit card that money. Right??

Not so fast. I’m gonna let you in on a little secret that may actually be super obvious to people but that I had to do a bunch of research to actually figure out: when you cancel a flight on Southwest, that credit gets added to your “travel fund” balance on your Rapid Rewards account (I don’t know how it works if you don’t have a RR account, but I figure if you’re going to fly on any airline, you might as well register an account with them so your trips count as miles earned. It’s why I have United and Delta accounts, despite hardly ever flying with them. Although to be fair, I don’t have a Frontier account…).

To use part of the $223 in my travel funds for my rebooked Cents Positive flight, I would’ve needed to choose the option at checkout to pay with that and enter in the confirmation number for the now-cancelled flight. But because I didn’t know that, I instead added another $206 to my credit card and the travel funds sat unused in my account. Which is why you’ll see yet more spending on CP flights in October’s report after they originally showed up in September, and I most definitely did not see a $223 refund on my credit card. Oops.

I’ve learned my lesson now

You have to complete any travel with your travel funds within a year of when you originally booked the flight, which for me was late September. I wasn’t worried since I was sure I’d be taking at least one trip in the first two-thirds of 2019 and could find a use for that credit before it expired. Maybe another birthday-adjacent trip to somewhere warm and sunny since having a winter birthday is awful?

Enter in my family, and the fact that as of two weeks ago I learned we’re not doing Christmas at our (nice and driveable) house this year. Which meant I needed to buy plane tickets yesterday. At least I wasn’t going to have to pay for $223 of whatever it would cost to buy tickets (way too late. Why can’t we figure out our plans earlier?) since it was already sitting in my Southwest account.

I booked a direct flight out of DC leaving around 6:00pm for $140, which I was pleased with.

But sometimes I’m obsessive about still checking flight prices just in case, especially within the 24 hour cancellation period. The next day the 7:00 flight was $127 instead of the $140 it had been before. Again, I’m not above rebooking flights to save small amounts of money. So I cancelled the first flight, got that money added back to my travel funds, and booked the later flight with my credit for $13 cheaper.

And then the next day the 6:00 flight was available for $127 instead of $140; given that I preferred the earlier flight, I repeated the cancel/rebook song and dance. All with zero charges on my credit card. Doing so has meant keeping up with the confirmation codes of each cancelled flight so that I can use that credit for rebooking, but I’m more than willing to do so if it means being able to change flights at will.

But I wasn’t terribly happy with the price I paid for for my second flight; there were cheaper options but the one itinerary that was a decent time was at least $20 more expensive. Surely I could do better than $147 (which was really the remaining $83 of my travel funds and $64 on my credit card), right?

Time to look at points!

It’s all about the points

Starting last year, I began strategically opening Chase credit cards for the sign-up bonuses; I’ve said before how my first move was to open a Chase Sapphire Preferred for the 50k bonus points, which is travel hacking 101. And if you, too would like to jump into the world of travel hacking with a CSP, you can open one here. (And yes, that’s an affiliate link, so here’s the disclaimer: following that link will give you a 50k point bonus when you meet the minimum spend and give me a 10k referral bonus. Which would be lovely if you were so inclined. But ONLY if you can pay off your credit cards on time and in full every month!)

I also have a Business Ink Cash and a Freedom card, both of which accumulate Chase Ultimate Rewards points in the form of cash back that magically become travel points when you transfer them over to a travel card instead.

So far I’d used exactly zero points for travel. They’re there and using them for travel would be their purpose, but for some reason I’ve been extremely reluctant to touch my stash. Some of it is pure habit: I’ve never booked travel with points, so going by how much flights cost in cash is just my default. Besides, I’ve gotta keep accumulating for the day in the future that’s surely coming where I’ll need a bunch of points to travel across the world practically for free, right?!

Well that day hasn’t arrived yet, but I have dipped into my points for the first time.

Actual travel hacking

I looked up how many points it would be to book my second flight and found it would be 8,998 points. With the 2,000-something I had in my Rapid Rewards account from having flown Southwest a few times this year, I only needed to transfer over 7,000 from Chase. Only using 7k Ultimate Rewards points seemed like a way better price to pay than $150 for the flight, so I made the transfer, waited two minutes for the points to show up in my Southwest account, then cancelled the flight and rebooked it with points instead (and the mandatory $5.60 9/11 security fee you have to pay for every flight). And because I cancelled within the first 24 hours, I actually got that $64 difference refunded to my card instead of added to the balance on my account.

I don’t actually know what the valuation normally is for Southwest points (I told you I’m a very baby travel hacker!), but just under 9,000 instead of $147 works out to be about 1.6 cents per point. Maybe I’m missing out on some secret (like that Southwest points should only be used if the value is at least three cents per mile), but I am incredibly pleased with myself for booking my first-ever flight with points. So don’t burst my bubble if it turns out that’s actually a horrible valuation for Southwest points.

As I told Twitter:

Just booked a flight with points for the first time ever and I feel like a deity #whatisthismagic #travelhacking pic.twitter.com/uaPkbyPkjz

— Erin | Reaching for FI (@reachingforfi) October 30, 2018

So despite accidentally double-paying for my Cents Positive return flight (but hey, I got it for $17 off!), I managed to book flights over Christmas for the low price of $5.60 plus 7,000 points transferred from Chase to Southwest. That’s way better than whatever ungodly amount I was afraid I’d have to pay for holiday flights bought less than two months in advance, even with $223 already prepaid (assuming Southwest was my best choice for the holiday flights, which it did end up being, thanks to another sale). And I’ve still got a $96 credit left on my Southwest account from the original $223 (no but really, where should I go in February?).

Clearly I’m a travel hacking genius!

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[*]Y’all, I know flying is an absolute privilege. Lots of people can’t afford to do so at all, let alone multiple times a year! But one day my goal is to be to a level of financial security where—unless I have zero other options—I don’t even consider the cheap Frontier/other budget airline flights because the money saved isn’t worth the crappy experience.