Easiest island to get to?
 

Generally speaking what do you think are the cheapest and easiest islands to get to from the U.S.? (From major airports on east coast or Midwest.)

Well,
Cheapest really depends on what airline you choose and what type of specials they may be running. This changes all the time.

Easiest would be anything close that has direct flights, like Puerto Rico, Grand Cayman, T&C, Bahamas, etc.

From the East Coast (since that's where I live).
Puerto Rico first comes to mind.
Dominican Republic.
Nassau and GBI in the Bahamas.

As ScottB says, airfares vary greatly from airline to airline and from day to day. A lot will depend on when you plan to travel, where you go and where you are leaving from. Simply saying "from major airports on the east coast or mid-west" won't help you very much. For example, both Miami and New York are east coast cities but airfares from those places to the same island will be significantly different. You really need to be more specific about your departure city for anyone to be of real help.

That said, in addition to the destinations mentioned by ScottB, Jamaica and the Dominican Republic are easy to get to by non-stop flights from many east cost or mid-west cities and they have an abundance of economically priced hotels and resorts. You also have Cozemel and Cancun (although the latter is not technically an island). Both are close to the US and therefore an "easy flight" plus there are some of the lowest priced reorts and hotels in the Caribbean.

Give us some more specifics about your departure city, where you are thinking of going and what you like in a destination and what you want to do when you get, there then perhaps we can give you better advice.

Bahamas, Jamaica ....