Cuba, award ticket, and connections
 

I'm trying to find a award flight for a friend of mine. He is not a US citizen and wanted to go europe-Havana Havana-Chicago and chicago-europe
I found award availability but it seems booking this is nearly impossible as one ticket as all the frequent flyer programs put some limitations on the flights. Before I spend more time looking at this, is it even possible for him to fly something like Havana to Chicago now?
Other option would be getting him to Miami (Europe Miami Chicago Europe) award and just buying a round trip Miami to Havana

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.

I suggest getting an award EUR - ORD return and buy a revenue ticket from ORD to HAV return. Keep in mind that an award ticket may incur fuel surcharges that surpass the cost of the ORD-HAV ticket.

That might be the best, but probably do Europe-MIA, MIA-ORD, ORD-Europe as most awards would allow that stopover. And just get a cheap Y from MIA or FL to HAV and back

Yep whichever option works in terms of availability. Good luck.

Some FF programs allow stopovers and/or open jaws on RT award tickets and others don't. You need to follow the rules of the program where you're using the miles.

Well, yeah. Of course.