I think you are way off on your money. look in the sunday chicago travel sections to see what is available.
read the fine print of the plus plus plus.
jetskis and sailings are usually not included, and at a resort cost the better part of $100 a crack.
look into mexico. the flights are probably better, and mexico on the caribbean is one of the least expensive these days. jamacia used to be real cheap also.
check travelzoo for specials.