SU 150 would normally take him over US airspace. I will be interesting to see if this flight deviates from its usual route to stay out of it or if it will be tempting the government to force it to land like it did with the Achille Lauro hijackers in 1985.
Indeed. Currently over northern Quebec. I don't know how accurate that link is, but zoom in and check out how it follows the west coast of Florida before dropping into Havana. Hope he has a window seat.