Online Travel Annoyance #2 – The Dark Art of Flight Book­ing

[Note from editor: The Dark Art of Flight Book­ing originally published on]

I probably don’t have to tell you this, but booking flights – especially international flights – is a shadowy and mysterious process.

There are plenty of sites like KAYAKSkyscanner, and Hipmunk that try to make it easier and the information more digestible. They’re great. But the underlying process of finding flights and figuring out the itineraries that give you the most bang for your buck is something I constantly struggle with.

Why does KAYAK show one price but Delta’s site show another? Why do some sites show only certain routes or only some carriers?

Look at this example between KAYAK and Travelocity. Same exact flight, time, day, everything. But a huge price difference. (I didn’t go out of my way to find this example. It was the first test search I tried.)

I don’t understand the economics or politics between these companies and airlines or between the airlines and each other. It’s completely opaque to me.

But there’s more than just complex relationships that make this hard to figure out. Airline websites are notoriously bad. They’re riddled with clumsy user interfaces, obscure step-by-step processes, and even dark patterns.

Look at this example from American Airlines.

Here is a flight from Beijing to Chicago to be booked as a one-way ticket. The price is 1225.60 USD.

Here is a flight from New York to Beijing, a one-way ticket. The price is 1450.70 USD.

Here are the same two flights but this time, they are booked as a multi-city ticket:

You can buy them both for 1556.50 USD! Why?

Again, I’m not sure what’s going on here behind the scenes. Is it a “bird-in-the-hand-is-worth-two-in-the-bush” situation? American Airlines would rather have a guarantee you’ll fly twice rather than only once, even if it’s for nearly the same amount of money. Is that what is really going on? Maybe not, maybe it doesn’t actually benefit American Airlines. It might just be an unintended consequence of complexities of the flight booking world. Who knows?

And, like I said before, this is coupled with poor interface design. Interface design that feels almost intentionally bad. It is entirely believable that some ordinary user would go to, click “one-way” and buy two tickets. They might never realize that by clicking the “multi-city” link and using that form, they could save more than a thousand dollars.

The multi-city link: it’s not exactly a “click here to save a thousand dollars” button, is it?

Raise your hand if you think American Airlines would send that user an email alerting them of their mistake.

One more example, and this one is going to blow your mind. Below is a flight to be booked as a one-way ticket and the exact same flight to be booked as part of a multi-city ticket. Look at the price difference:

It’s insane. You would literally save 3000 USD by buying two tickets and throwing one away than you would by buying the first flight individually.

World of international flights: what is wrong with you?

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Will Moyer

A web designer, consultant, and photographer living in Beijing, China. More at

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