> I don't want it to decide to send me to a 37 hour trip with three stops because it is 3$ cheaper.

This sounds hard; as in: if you can define and enforce what a good enough response from an LLM looks like, you don't really need the LLM

> what is the intent.

For the HR person you have a human with intents you can ask; for an LLMs it's harder as they don't have intents