How do I get to the city when the plane lands

Hint 1 of 8:

The most important thing here is to save Kate.

Hint 2 of 8:

Who is better at healing?

Hint 3 of 8:

Chi is.  Try getting Lucky to leave through conversation.

Hint 4 of 8:

Here is one conversation path that should work:

Hint 5 of 8:

2) I'm fine, but cold.