People frequently ask Where Does Delta fly Caribbean? Several popular Caribbean locations are serviced by Delta Air Lines, including 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. These locations provide chances for adventure and leisure, as well as stunning beaches and varied cultures. Since Delta's flight routes to the Caribbean sometimes change, it is always advisable to visit their official website for the most recent details on possible locations and schedules.