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Should You Pay Someone to Book Your Flight With Points?

Are your credit card points taking you as far as they could?

For the past year, you’ve been buying truckloads of toilet paper, hoarding paper towels, and stocking up on canned goods for the apocalypse. And if you were smart, you did all of that using a rewards credit card that accrues thousands and thousands of airline miles.

If you are, in fact, one of the smart ones who plays with cards to earn points for those long-haul flights overseas, there’s a new company that wants to help you spend them—and spend them very wisely.

That company is Chatflights, started by entrepreneurial brothers Alexis and Malte Barnekow.

“The concept is very simple,” said Malte Barnekow, president of Chatflights. “When it comes to award travel, we have this app experience where you’re chatting with a human being as opposed to a bot. And that human being is an expert at flight travel. We know everything about mileage runs and award redemption, open jaw complex travel, multiple destinations, multiple classes, all of that stuff, we go really, really deep in-flight travel, in particular.”

“When it comes to award travel, we have this app experience where you’re chatting with a human being as opposed to a bot. And that human being is an expert at flight travel.”

The nuts and bolts of the business go a little like this: the company charges a fee to book business and first-class flights using your miles. But what they do is check specifically for award seats that are actually different than the seats you might buy using miles on an airline’s website. These are seats that airlines don’t typically sell for cash and usually disappear quickly. Chatflights monitors these seats and alerts customers when they’re available for a flight the customer might have been looking for.

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“If you are flying from New York to Tokyo, a saver class seat, like an award seat that we find can be 80 or 90,000 points in business class. That exact same seat bought on is 830,000 points, it’s 10 times more. These seats are few and far between, so you have to know how to find them,” Barnekow explained.

1. Qantas International First Class Lounge at the Sydney Kingsford Smith airportEQRoy/Shutterstock;
Matej Kastelic/Shutterstock;

The fees for these services are $350 per person for a business class seat or $450 per person for a first-class seat. And for people asking why they should pay for a service they can do on their own? The answer to that question ultimately comes down to what you think your time is worth. The experts at Chatflights will work with you through their app (no bots) and find the best deal for you without any of the hassles.

If you do want to use a service like Chatflights, the way to make it the most beneficial for that steep fee is to have the maximum amount of flexibility in your schedule. If you give Chatflights a single day in which you can leave and return, your results might not be that great. But if you give them a week to play with on both legs of your journey, the benefits could be enormous. The other thing to be aware of, Chatflights will tell you that it’s almost never worth using points on an economy class ticket and especially not worth using points unless you’re on a long-haul flight.

Is this worth it? That’s a question you’ll have to answer for yourself. Again, what is your time worth? But if you’re planning a trip abroad, with a lot of flexibility, and you want to travel in style, give Chatflights a try and see how far you can push those pandemic miles you earned this past year.