[takinola]

Booking a flight is the type of thing you think you want to dedicate your full attention to. Largely, the issue is one of trust that whatever is making the bookings will take into account the nuances of your schedule and preferences. Here's the typical flow for how my (human) assistant books my flights. I tell them I want to go to $LOCATION from $START to $END. They have my calendar, my travel preferences (airlines, hotels, etc) and the company travel policy. A couple hours later, they slack me a couple of options. If there is one I like, I tell them to book it. If not, I tell them why none of the options work. The process repeats until I see something I like or we run out of options and I have to choose the least bad option. There is nothing about this process that needs a human. It's all done on Slack and for all I know the person at the other end is actually an AI (they're not, but for arguments sake, they could be).