Southwest Airlines Caribbean Flights

With Nonstop Flights to Aruba and Beyond

Jamaica, Negril, People jumping into ocean from footbridge

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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

Currently, Southwest Airlines services flights to Aruba; Belize City; Grand Cayman; Havana; Montego Bay; Nassau, Bahamas; Punta Cana; San Juan, Puerto Rico; and Turks and Caicos.

Although there are many connecting flights from major U.S. cities to the Caribbean, there are only 11 airports that provide direct flights to these tropical island destinations: Baltimore-Washington International Airport (BWI); Chicago Midway International Airport (MDW); Denver International Airport (DEN); Fort Lauderdale-Hollywood International Airport (FLL); Hartfield-Jackson Atlanta International Airport (ATL); Nashville International Airport (BNA); Orlando International Airport (MCO); St. Louis Lambert International Airport (STL); Tampa International Airport (TPA); and Houston's William P. Hobby Airport (HOU). Read on to see which U.S. cities offer nonstop flights to each Caribbean destination served by Southwest Airlines.

Cities that service nonstop flights to Aruba:

  • Baltimore-Washington
  • Fort Lauderdale
  • Houston

Cities that service nonstop flights to Belize City:

  • Denver
  • Fort Lauderdale
  • Houston

Cities that service nonstop flights to Grand Cayman:

  • Baltimore-Washington
  • Fort Lauderdale
  • Houston

Cities that service nonstop flights to Havana:

  • Fort Lauderdale
  • Tampa

Cities that service nonstop flights to Montego Bay:

  • Baltimore-Washington
  • Fort Lauderdale
  • Houston
  • Orlando
  • Chicago
  • St. Louis, MO

Cities that service nonstop flights to Nassau, Bahamas:

  • Baltimore-Washington
  • Fort Lauderdale
  • Houston

Cities that service nonstop flights to Punta Cana:

  • Atlanta
  • Baltimore-Washington
  • Fort Lauderdale
  • Houston
  • Chicago
  • St. Louis, MO

Cities that service nonstop flights to San Juan:

  • Nashville
  • Baltimore-Washington
  • Fort Lauderdale
  • Houston
  • Orlando
  • Chicago
  • Tampa

Cities that service nonstop flights to Turks and Caicos:

  • Baltimore-Washington
  • Fort Lauderdale

When you reach cities like Havana, Turks and Caicos, the Grand Cayman Island, or Belize City, you can easily book a connecting flight on a regional airline that services more of the Caribbean.

Other Airlines

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 Caribbean-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), Havana, and the Dominican Republic (Santo Domingo).

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