Southwest Airlines, long renowned for its low fares and great customer service, only recently began flying internationally, and many of its first non-U.S. destinations have been in the Caribbean. While some routes were inherited from AirTran Airlines, which merged with Southwest in 2011, others represent an expansion of Southwest's own route system.
Southwest was one of a handful of U.S. airlines awarded routes when direct flights resumed between the U.S. and Cuba in 2016, so while Southwest may not always be the low-fare leader it once was, travelers still benefit from the carrier's "no baggage fees" policy and the increased competition to Caribbean destinations.
Other major carriers flying from the U.S. to the Caribbean include American Airlines, JetBlue, Delta, and United, but the best way to get around the Caribbean is to first fly into one of the islands like the Bahamas then take a Caribbean-based airline to one of the smaller islands.
Where They Fly
Although there are many connecting flights from major U.S. cities to the Caribbean, there are only five cities that provide direct flights to these tropical island destinations: Houston, Orlando, Fort Lauderdale, Atlanta, and Baltimore/Washington, with occasional Saturday service from Milwaukee.
Currently, Houston, Orlando, Fort Lauderdale, and Baltimore/Washington airports service nonstop flights to Aruba. while Cancun has daily nonstop flights from Atlanta, Baltimore/Washington, and seasonal Saturdays from Milwaukee.
You can get to the Nassau Airport in the Bahamas or San Jose in Costa Rica on nonstop flights from Baltimore/Washington Airport or to Montego Bay in Jamaica or Punta Cana in the Dominican Republic from Atlanta, BWI, Orlando, Chicago/Midway, and seasonal Saturdays from Milwaukee.
Additional flight paths connect to Havana, Varadero, and Santa Clara in Cuba as well as the Turks and Caicos, the Grand Cayman Island, and Belize City, where you can easily book a connecting flight on a regional airline that services more of the Caribbean.
There are many regional airlines that offer service to the Caribbean islands including American-based companies like JetBlue, United, and Delta; however, it's much more likely to get service to smaller islands on Carribean-based airlines.
The Trinidad-based Caribbean Airlines offers flights throughout the islands including destinations in Barbados, Antigua, Jamaica, Trinidad & Tobago, and Saint Lucia while WinAir offers service to Anguilla, Antigua, Montserrat, Saints Kitts & Nevis, Saba, Saint Barths, Saint Eustatius, Saint Maarten, and the British Virgin Islands (Tortola).
LIAT Airlines services the most islands, though it is almost exclusively inter-island instead of international with no service to United States cities excluding the U.S. Virgin Islands. LIAT offers flights between Santo Domingo in the Dominican Republic , San Juan in Puerto Rico, St. Thomas and St. Croix in the U.S. Virgin Islands, the British Virgin Islands, St. Maarten, Anguilla, St. Kitts & Nevis, Antigua, Guadeloupe, Dominica, St. Lucia, Barbados, St. Vincent & the Grenadines including Bequia, Grenada, Trinidad & Tobago.
BahamasAir also offers several intra-island flights including destinations in the Bahamas (Nassau, Grand Bahama, Abacos, Andros, Eleuthera, Cat Island, Great Exuma, San Salvador, Long Island, Crooked Island, Mayaguana, Acklins, Little Inagua, Great Inagua), Turks & Caicos, Cuba, Jamaica (Kingston), and the Dominican Republic (Santo Domingo).