I Let a Bot Plan My Vacation, But the Next One I'll Book Myself

Hipmunk’s new AI travel assistant works, but can you trust it enough to not check other sites anyway?

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Nov 17 2015, 7:10pm

Image: Josh Beasley/Flickr

I despise traveling. Not the part where you get to explore a new place, or maybe visit a friend, or relax in a gorgeous setting—the part I hate is the part where you have to go to the airport and get on a plane.

So I'm always looking for ways to make the process easier and more efficient, and I was intrigued when I learned that travel service Hipmunk is launching a new feature called "Hello Hipmunk," where an AI can suggest flights and hotels based on entries in your calendar, or if you CC it on an email.

In a Hipmunk blog post, senior product manager Alex Quintana explained the inspiration behind Hello Hipmunk. "I thought that if we could enable people to copy Hipmunk in on the message, they could get a head start on travel planning. We would eliminate that dreaded 'to-do' by enabling people to delegate to Hipmunk as a travel assistant." On the surface, this is a great idea that addresses a common consumer pain point—but anything involving an AI can be tricky, and that's why I gave it a spin.

Luckily I have a car and don't have to fly home for the holidays, but I pretended I did. My hometown is just outside of D.C., but the AI didn't recognize "D.C.," and instead returned flights to San Diego. I reached out to Hipmunk to ask what was up, and the company told me in an email that it had looked at my query and put it on a "stumped the munk list." "We'll need to investigate it a bit more to see what elements of the inquiry made The Hipmunk think that you were flying to San Diego."

Image: Rachel Pick

The AI did successfully recognize "DC" and "Washington, D.C.," but curiously in all the tests I conducted it only returned flights on American Airlines. I thought this was weird, but it turned out to be the result of a useful feature. As Hipmunk explained: "We return the top three least agonizing results. We are known for our agony score that takes into account price, duration and number of stops. It just so happens that American Airlines has the top three least agonizing flights."

I tried the hotel feature as well, and it worked just fine. But I found myself wishing you could break it down further, requesting hotels in a certain neighborhood or at a certain price point. It also only returns three hotels, though you can click through to the main site to see more.

It's worth noting that Hello Hipmunk is still in beta testing, and the AI will improve over time as more people use the service. It's worth giving it a shot and seeing if it works for you, but I wonder if enough consumers will trust an AI to make important travel decisions for them, without first comparing results on sites like Kayak and Priceline.

As for me, I'll try anything once if it promises to make flying easier—but I'll probably plan my next trip on my own.

Update: After this story was published, a human being at Hipmunk reached out to Motherboard offering some neighborhood-specific hotel search results.

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