Many People have a question:  Where Does Delta fly Caribbean? Flights are available from a number of Caribbean cities, including well-known ones like San Juan in Puerto Rico, Punta Cana and Santo Domingo in the Dominican Republic, Nassau in the Bahamas, Montego Bay and Kingston in Jamaica, St. Thomas in the U.S. Virgin Islands, St. Maarten in Aruba, and Grand Cayman in the Cayman Islands. Beautiful beaches, vibrant cultures, and chances for adventure and relaxation may all be found in these places. It's recommended to check the official website of the airline for the most recent details on available destinations and itineraries as Delta's flight routes to the Caribbean sometimes change.