One of the things I enjoyed the most during my time at Hipmunk was Fly Club. It was a service for really cool flight deals delivered by a chatbot. The bot knew the users’ interests and home airport, and using a data model we jerry rigged together, it sniffed out upcoming flights to places that were interesting. On average, the prices were 35-60% below normal.
The cities — origin and destination — were totally human curated. But the search was powered by automation. Fly Club illustrated a strong belief of mine that automation supporting humans can create truly delightful experiences.
For example, we found roundtrip flights from San Francisco to New York for $88. To Stockholm for $350. They didn’t last long, but the chatbot would push you a notice into your messaging app when it found these deals.
It’s a bit sad to discontinue Fly Club due to other focus, but it’s an idea I’d like to come back to.