The secret to cheap flights? Check prices after booking.



Welcome to The Upgrade, By The Way’s new series on travel hacks and hot takes. See how to submit here.

I’m that person who responds to compliments about my outfit by sharing how much I spent on it. Oh, this sweater? Got it on sale. I might even tell you how much I saved on the gift you’re unwrapping. After all, it’s the deal that matters.

I come from a long line of deal-hunters. Some of my happiest memories as a kid were weekends spent discount-shopping with my mother and grandmother; my mom talks about doing the same with her Italian immigrant grandmother. I’m also a chronic returner; I’ll take something home, think about it and return it later if it isn’t right.

In the rare case I buy something full-price, I’ll monitor whether it goes on sale, then call the store for a price adjustment. So when I started traveling frequently as an adult, it made sense for me to apply these important life skills.

How do you actually get those $49 flights? There’s always a catch to airline sales.

Sure, everyone knows to shop around for the best prices on airfares, hotel rooms and rental cars. But the savings don’t have to end after you hit “purchase.” This is why I stalk travel prices even after I buy, every day, multiple times a day, until I see the price drop — and then pounce.

I felt as if I’d found some sort of cheat code with the airline. I’d never felt more alive.

Thanks to the pandemic’s flexible booking policies, it’s much easier to cancel to get a credit on flights than it was pre-2020. (You can always cancel a flight within 24 hours of booking.) Many airlines dropped change and cancellation fees, making it easier to adjust your trip. What they might not want you to know is this also makes it easier to save money.

Exhibit A: A few weeks ago, I saw the price on my Christmas flight home to New Jersey drop by $70 a few days after I purchased it through United Airlines. Because I had a fare that wasn’t basic economy, I canceled the flight, immediately received a credit in my email and rebooked the same flight — banking the $70 credit. I quickly used that money for an upcoming trip to Belize.

I felt as if I’d found some sort of cheat code with the airline. I’d never felt more alive.

Southwest, which didn’t have change fees before the pandemic, makes this hack even easier. Its app features a “change” button and quickly shows you the cost difference for booking a new flight, both in money and points. I use this button, wait for the price to go down, rebook the same flight and bank the credit. (I also recently bought points at 35 percent off to complete a flight purchase, but that’s an Upgrade for another time.)

Your conspiracy theories on Southwest’s boarding policy are wrong

This technique works on more than just flights. In fact, rental cars may be the easiest place to do it; most bookings don’t require you to pay upfront, so it’s very low risk. For a trip to Las Vegas in spring — at the height of surging rental-car prices — I rebooked my rental four times and saved more than $200 in the end. I don’t pretend to have invented this method; deal master Scott Keyes of Scott’s Cheap Flights is also a fan.

I’ve had less success with hotel rooms, but it doesn’t mean I don’t try. I often use for hotels (yes, I know the drawbacks on booking on third-party platforms), which shows rooms with free cancellation and “pay at the property” rates.

The whole thing is a game for me: I don’t set price alerts; I just obsessively check. I’m sure there are more efficient ways to do this, but this is me. Some people play the lottery. I gamble on travel prices. The thrill might be even better than the travel itself.

And every time I save, I always text my mom.

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