(1) The smuggler’s route
Probably the riskiest but most Hollywood-friendly option would be for Snowden to sneak onto an already scheduled flight from Moscow to Havana to Caracas and simply hope he doesn’t get caught. Maybe that means flying under a false name if it’s a commercial flight or boarding a cargo flight. The flight path would probably take him over U.S. airspace, as well as that of several U.S. allies: Canada, Norway and Sweden. The map above shows the route of Monday’s Moscow-Havana flight, which spent several hours over the United States.
Pros: Fastest route, cheap and simple. Option for a cool disguise, possibly borrowing from the Russian security services’ wig collection.
Cons: As Snowden knows, the United States has significant espionage capabilities. And he was initially supposed to fly to Havana but bailed; it’s not clear why, but it’s possible he had reason to believe the flight would not be safe for him.