I have heard the Obama administration is planning on easing flying restrictions between the USA and CUba in the future but I believe that right now it is still only possible to fly there if you are a Cuban American and flights (charter flights) are only available from a few cities in the USA. Most Americans who want to visit Cuba do so by flying to another country,ie.Canada or Mexico and getting a flight from there.
I'm not totally up to date with current regulations but I'm pretty sure this was the situation in 2010.

It won't be easy! USA to Cuba flights are still very restrictive. You could look at routing via Toronto (YYZ) and picking up a Canadian charter flight to Cuba. These will often be the cheapest way to fly between Canada and Cuba.