The secret of cheap flights? Check prices after booking.


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

I’m the person who responds to compliments on my outfit by sharing how much I spent on it. Oh that sweater? I have it on offer. I could even tell you how much I saved on that present you’re unwrapping. After all, it’s the deal that counts.

I come from a long line of deal hunters. Some of my happiest memories as a kid were weekend discount shopping with my mom and grandmother; My mother talks about doing the same with her Italian immigrant grandmother. I’m also a chronic returnee; I take something home, think about it, and return it later if it’s not right.

On the rare occasion that I buy something at full price, I monitor to see if it goes on sale and then call the store for a price adjustment. As I began to travel frequently as an adult, it made sense for me to practice these important life skills.

How do you actually get those $49 flights? When it comes to air sales, there’s always a catch.

Sure, everyone knows how to shop around for the best prices on airline tickets, hotel rooms, and car rentals. But the savings don’t have to end after you click buy. For this reason, I follow the travel prices even after the purchase, every day, several times a day, until I see the price drop – and then strike.

I felt like I found some kind of cheat code on the airline. I had never felt more alive.

With the pandemic’s flexible booking policies, it’s much easier to cancel flights to get credit than it was before 2020. (You can always cancel a flight within 24 hours of booking). Many airlines have lowered change and cancellation fees, making it easier to customize your trip. What they might not want you to know is that it’s easier to save money too.

Exhibit A: A few weeks ago I saw that the price of my Christmas flight home to New Jersey had dropped by $70 a few days after I bought it through United Airlines. Since I was on a fare that wasn’t Basic Economy, I canceled the flight, received an instant credit in my email, and rebooked the same flight – depositing the $70 credit. I quickly used the money for an upcoming trip to Belize.

I felt like I found some kind of cheat code on the airline. I had never felt more alive.

Southwest, which had no exchange fees before the pandemic, is doing this hack even easier. Your app has a “change” button and will quickly show you the cost difference for booking a new flight, both in money and in points. I use this button, wait for the price to drop, rebook the same flight and book the credit. (I also recently bought 35 percent off points to complete a flight purchase, but that’s an upgrade for another time).

Your conspiracies regarding Southwest’s boarding policy are false

This technique does not only work for flights. In fact, rental cars may be the easiest place to do this. Most bookings do not require you to pay in advance, so the risk is very low. For a trip to Las Vegas last spring – at the peak of rising rental car prices – I changed my rental car four times and ended up saving more than $200. I do not claim 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 that doesn’t mean I don’t try. I often use for hotels (yes, I know the disadvantages of booking on third-party platforms) that show 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’m just checking compulsively. I’m sure there are much more efficient ways to do this, but I am. Some people play the lottery. I play on travel prizes. The thrill might even be better than the journey itself.

And every time I save, I text my mom.

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