Originally Posted by
jason8612
.... is it even possible for him to fly something like Havana to Chicago now?
Now? As in the time period after 45's announcement about what he hoped would happen and the issuance of any new guidelines by US government offices at some unknown time in the future?
As of this writing,
nothing has changed.
Some people are concerned that their trips may be audited at some unknown time in the future by an agency (OFAC) which currently does not have funding for staff to do so, for activities in a country they really can't check up on details for, or worried about being questioned by CBP at the return airport, so they are hesitating to travel.
A foreign passport holder like your friend likely has much less chance of ever being tracked down to be audited IMO.
He does, however, still have to travel under the current rules, which means he must choose one of the official OFAC reasons for travel, possibly even only for a return flight only if the airline chooses. Many now are choosing the vaguely defined "support for the Cuban people". He should never say the word 'tourism'. Travelers are told to keep "proof" of their activities for 5 years.
Happy travels to him. You should go and enjoy the country with him.