How I Scored $22 Plane Tickets to Puerto Rico

I’m not typically the world’s most spontaneous person. When I buy something significant, it’s usually after a long hard look at my finances, and there’s a fair bit of price comparison that goes into it as well. A vacation? I’ll stew on that for months. So if someone came up to me and said, “Do you want to go to Puerto Rico at Thanksgiving?” but said I had to make my mind up that instant, it would be a pretty easy pass.

Except last week I bought plane tickets to Puerto Rico twenty minutes after I first had the idea to go there for Thanksgiving. Why? Because they were $22 each, round trip. I bought tickets for my family of five to fly at Thanksgiving for a total of $110, including tax. (Technically, the tickets were $1 each way. The rest of the cost was airport fees.)

I posted about this on Facebook, hoping some friends might be able to nab the same deal. Within an hour or two, however, the deal was gone. So how did I manage to get such ridiculous airfare?

Honestly, I got lucky. But that said, I did a few things ahead of time to put myself in a position where luck could help me out.

First off, I have a travel deals blog that I check most days. The Flight Deal lists great prices on airfare from a number of American cities. I’ve been watching them for about two years. Boston is the largest close city that they cover, so I just skim the deals for mention of Boston, and then perk up if I see anything good. I’ve seen tickets to Asia for $400, for example. But often the prices are contingent on things I just can’t do right now. With kids at home, Denisa and I can’t just up and go to Tokyo two weeks from tomorrow. (Well, assuming anyone was going anywhere, that is.) So it’s been more an exercise of “someday maybe I’ll be able to buy one of those tickets . . .”

In light of all the garbage happening in the world right now, I’d stopped even looking at the blog for the last while. Then last week I saw a news story in the morning about how cheap airfare was right now, and how now was the time to buy. It was enough to make me curious. I poked around on Kayak some for European fares. They were low ($450 at the right times), but none of the times worked for me, and it wasn’t as if I was going to pick now to plunk down $2,500 in plane tickets for something six months from now.

I shrugged off the idea and moved on, but when it came time to check my daily blogs, the article was enough for me to check my travel blogs again. And that’s when I saw the rate: Boston to Puerto Rico for $20.

It had to be something weaselly, like you could only fly on the third Wednesday of a month on a red eye. Or maybe it was with some sketchy carrier. I checked it out, though. Jet Blue. And when I checked the travel dates, it was for anytime until the end of the year. Summer still seems like it might be iffy for travel, so the next window my family could go would be Thanksgiving. Surely that would be more expensive.

I checked. It wasn’t. I read the fine print. The tickets are fully refundable, meaning if the world hasn’t settled down by then, I could get my money back. I sent the price to Denisa, we talked about it for a couple of minutes, wondering what the angle was we weren’t seeing. How in the world could it be that cheap?

We bought the tickets.

As I said, a few hours later, the deal was gone. Those same tickets I had bought for $110 now would cost $3,800. I waited for JetBlue to contact me and explain it had all been a pricing error. A week later, the trip is still good to go. All signs point to yes, assuming flying is allowed by then.

So like I said, I was lucky with this airfare. But if I hadn’t been checking travel blogs, I wouldn’t have gotten lucky. Will I do it more often? Probably about the same as I’ve always done. There’s only so often I can pick up and head out on a big trip.

But it never hurts to check . . .


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