Originally Posted by
YVR Cockroach
At this point, it will still be cheaper and easier to fly from Canada. Flights from the US are still charters and require licensing and are fairly expensive (not to mention not available to non citizens/permanent residents).
You should be o.k. going to Cuba and re-entering the U.S. if you are not considered a U.S. person.
One doesn't need to apply for a license for a charter now as you can travel under a general license using one of the twelve broad categories. As far as returning to the US there hasn't been an individual fined for traveling to Cuba in the last several years, and I would be surprised if that changed under the current adminstration. Of course who knows what will happen in the future.
Cheers
Howie