When travel startup Hipmunk launched five years ago, its big selling point was a better interface for searching and browsing flights. Now the company is looking to help users even before they start searching for travel options, through the launch of a new set of features called Hello Hipmunk.

The company describes this as a “travel planning assistant.” Basically, Hello Hipmunk is an umbrella term for two products, one allowing users to interact with Hipmunk over email, another providing travel recommendations based on the events in your calendar.

On the email side, there’s Hello Email. You send an email to [email protected] with a question like “What hotels are available in Austin, TX from Nov 20 – Nov 23?” and you’ll instantly get an email back with recommendations — if you see something you like, you can just follow the link from the email and book directly.

I also tried out less precise queries, like asking for flights “next weekend” or hotels “around Christmas” and Hipmunk came back with more-or-less decent results. (In one case I asked for flights and instead received recommendations for hotels, but I got an apologetic customer service email offering to help a couple of hours later.) You can even cc Hipmunk on an existing email thread.

Hello Calendar, meanwhile, scans your calendar, specifically the “where” field) for events that take place more than 100 miles from your “home” airport. When it finds them, it provides links to recommended flights, hotels and rental cars. (Note: Not surprisingly, this is less reliable when your calendar entries are sketchy or downright cryptic, as most of mine are.)

If it works, Hello Hipmunk could eliminate the need for confusing or frustrating searches from your travel planning. It could also keep users coming back to Hipmunk before they even consider visiting another travel search site.

“By ‘reading’ people’s emails and calendars (with permission, of course), Hello Hipmunk instead infers people’s travel requirements and provides recommendations on the best options (e.g. flights, trains, hotels, vacation rentals), making it so they never have to type anything into a search engine,” said CEO Adam Goldstein via email.

Featured Image: Hipmunk

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Hipmunk Aims To Become Your Travel Assistant With New “Hello Hipmunk” Features