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There are no direct connections. You would have to travel to Miami and then take a flight. It is very expensive to go from here to Jamaica (it costs Dominicans more than to go to Europe!).
You would have to charter a boat and that will cost a bundle. It is very possible that you may take a cruise ship that makes a stop in Jamaica and in the DR.
Double check with your travel agency, but if there are no flights from the DR to Jamaica, it is less likely there will be flights from Haiti to Jamaica. There are direct connections to Cuba or Puerto Rico.