With “Hello Hipmunk,” Hipmunk Does Travel Planning Inside Your Email And Calendar

A dash of artificial intelligence lets you search for flights and hotels without actually searching for flights and hotels.

With “Hello Hipmunk,” Hipmunk Does Travel Planning Inside Your Email And Calendar
[Photo: Flickr user Sunghwan Yoon]

Hipmunk is my favorite travel shopping service for one reason: It has the simplest, most usable, least cluttered interface. But starting today, it’s adding a couple of features that help you start planning for trips without visiting the site or app at all.


The company bills Hello Hipmunk as a virtual assistant. I haven’t seen anything like it before, but its conversational approach to artificial intelligence and anticipatory leveraging of your personal data put it into a broad category of services that also includes Siri, Google Now, Microsoft’s Cortana, the X.AI and Clara scheduling tools, and more.

If you cc: on an email discussing travel plans–such as a message to your spouse about an upcoming vacation–it will attempt to figure out where you’re going and when, and then will cc: all with a message containing hotel and flight suggestions. (You can also just send an email to the service directly.) If it needs more information–when I tried it with a message about a plane flight, I forgot to mention a departure point–it will ask for it.

Similarly, if you give Hello Hipmunk permission to monitor your Google Calendar and are careful to plug in location information relating to upcoming plans in distant cities, the service will email you with travel recommendations.

“The idea for some sort of personal travel assistant has been bouncing around in our heads for several years,” says Adam Goldstein, cofounder and CEO of Hipmunk. But it was only this year that the company was confident enough that it could understand enough about travel intentions expressed in free-form text to implement the idea in a way it thought was useful enough to pursue.

And even though Hello Hipmunk’s is so different from Hipmunk’s core site and apps, the overarching goal–to make planning as painless as possible–is the same. “People often put off the decision to book travel because it seems like a lot of work,” Goldstein says. “I do it myself, and I run a travel site.”

It’s easy to envision the basic idea existing in multiple forms–as a bot you can reach via instant-messaging apps, for instance, or by using Siri-like voice input. “We started with email because it made things easy to test,” Goldstein says. “But the technology is designed so it could work in all sorts of communication.”


There are also lots of ways in which the service could be smarter. Right now, for instance, it has no persistent memory of your travel preferences, such as favorite hotel chains, which means that every planning session starts as a blank slate. Goldstein told me that’s because many people have varying desires depending on whether they’re travelling for work or pleasure, and the company doesn’t want to rush out a feature that might guess wrong. Over time, though, it plans to make this virtual assistant brainier and brainier–and the smarter its recommendations get, the better they could be for Hipmunk’s bottom line.

About the author

Harry McCracken is the technology editor for Fast Company, based in San Francisco. In past lives, he was editor at large for Time magazine, founder and editor of Technologizer, and editor of PC World.