Last updated: 01:00 PM ET, Fri November 27 2015

Tech of the Week: Hello Hipmunk Brings Awesome AI To Your Email and Calendar

Travel Technology | Gabe Zaldivar | November 27, 2015

Tech of the Week: Hello Hipmunk Brings Awesome AI To Your Email and Calendar

Images courtesy of Hello Hipmunk

Hello Hipmunk has arrived like an all-knowing pal who has the skinny on airfare and hotel accommodations.

The new innovation from travel site Hipmunk acts like a crafty artificial intelligence travel agent that springs into action when copied on an email or when the service is allowed access to your calendar.

It’s really that easy. You essentially ping Hello Hipmunk on, say, an email chain with friends and family as you discuss a future vacation.

And from there the group gets information on myriad possibilities.

Hipmunk describes the two innovations as the following.

Email: “Users ask Hello Hipmunk questions by emailing hello@hipmunk directly, or adding hello@hipmunk into the CC line when writing an email about travel plans. (e.g. “Hey, Jane, let’s get a hotel in Miami Beach Dec. 4 to 6?”). Hello Hipmunk will email back the best flights (or trains) and the best hotels or vacation rentals for that trip, instantly. Users can then click through to or the Hipmunk app to review options and book.”

Calendar: “Hipmunk’s powerful patented calendar integration anticipates travel plans, bypassing the need to reach out to Hipmunk in the first place. Users give Hipmunk permission to access their Google Calendars; Hipmunk periodically scans them to find events users are attending in another city. Then, Hipmunk emails flight, train, and hotel or vacation rental search information for those travel dates. On Hipmunk’s website, customers can then see which flights fit into their schedules, and which hotels are located near their meetings.”

We had the pleasure of touching base with Roxy Young, Hipmunk's Vice President of Marketing.

Young let us in on various aspects of the technology, including its privacy and infrastructure.

TravelPulse: Where did the idea for Hello Hipmunk come from?

Roxy Young: Hipmunk's mission is to make travel planning simple and delightful. The concept of Hello Hipmunk has long been a vision for the company, and the technology is finally at a point where we are able to deliver accurate and actionable travel suggestions.

TP: Can you describe a bit what happens on the back end of the technology? What is taking place behind the scenes to get quick and efficient recommendations sent via email or placed on the calendar?

RY: In the case of Hello Email, we use an AI engine that deconstructs the contents of an email into components that we can respond to with actionable travel recommendations. These components include items such as identifying destinations, dates and type of travel need such as flight or hotel. In developing the feature, we trained the engine to interpret the components using our Customer Service inquiries, as many of them are for travel planning assistance. Additionally, we will continue to use humans to fine-tune how the engine interprets the components, so that it better understands the nuances of natural communication.

When people opt-in to Hello Calendar, they provide their home airport. Hello Calendar is looking for events that are >100 miles from person's home airport based on events and their corresponding locations on the calendar.

TP: Of course, we live in an age where people are stingy with their privacy settings. What might you say to allay those fears when using Hello Hipmunk?

RY: When people opt in to Hello Calendar, they see a Request for Permission modal from Google that lists the items Hipmunk has access to for Hello Calendar. It's similar to other Google connect services. If someone isn't comfortable granting access, they can simply "deny" access. It is an opt-in service only, and you can opt out at any time.

TravelPulse: So if the user allows for Hello Hipmunk to search say the Google Calendar, what is actually being scoured? What are the tech's limitations on one's privacy?

RY: Google lists the items Hipmunk has access to for Hello Calendar... The information Hipmunk has access to is disclosed on the Request for Permission modal upon signup.

TP: I guess the same question goes for email. Will Hipmunk only see what it is being cc'ed on?

RY: Yes. Hello email can only "see" emails that are directed to

TP: Let's say a traveler is eager to get up and running. Is it as easy as plunking in your email address?

RY: That's our mission — to make travel planning simple and delightful. People can start using Hello Email by including and start using Hello Calendar by going to

TP: Lastly, is there anything you think travelers might need to know about this new innovation?

RY: We think Hello Hipmunk is the future of travel planning. We've integrated into channels people already use like emails and calendars and our products are anticipating people's needs with relevant, actionable results.


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