Originally Posted by Winkdaddy

In the past, USA based airlines could obviously not fly over countries like the Soviet Union, but much has changed since then and now I suspect almost all airlines can fly over Russia. So, what countries are left that do not allow USA based carriers, or any other foreign based airline to violate their airspace? I am pretty sure North Korea is one, but who are the others?

Do we fly over Cuba to get to Jamaica and the Caymans, or do we go all the way around??