First of all Welcome to steemit! I am here for a few days only as well and I am still discovering everything! I have read through a bunch of texts of other people and really like the vibes of this platform! I really enjoyed your story and am impressed by the amount of countries you have already visited - I am definitely looking forward to hearing more stories!!
I like the fact that you didn't finish your story and asks questions :) it feels just like being back in school in creative lessons or so...
my answers:
(1) the captain told you that you couldn't land in Chicago because of bad weather and that you had to fly back to another city were you were authorized to land? (worst case scenario - of course I would wish something else to have happened)
(2) In this case you would not have landed in Chicago but instead in another city.
(3) I guess in the end you did reach the United States, but the question is when you reached it...right?

I am excited about the second part of your story!! Keep in writing these nice stories and good luck!