If you don't have passports, you may want to go to the U.S. Virgin Islands, St. Thomas (easiest) or St. John (lush).
Or Puerto Rico. There are direct flights from ORD to SJU.
I would agree with the previous posters suggestions re SXM or AUA. But you should also consider BGI, one of my favourites.
And if you are set on having an all-inclusive vacation, consider MBJ and PLS.
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13F