One of the easiest ways to minimize airport time is to opt for the fewest flight connections as possible. For many East Coasters, that makes the beaches of the Caribbean a convenient option, with dozens of nonstop flights between major hubs and the islands.
This winter brings some notable route additions: United is reviving Newark to St. Croix service for the first time in three decades, BermudAir is launching nonstops from Boston and Newark to Anguilla and Turks and Caicos, and Delta is adding a second daily flight from Boston to Aruba. (There are also a few missing flights: JetBlue will not fly to Antigua this season, and Spirit's shutdown in May 2026 removed several budget routes from the map.)
Here is the latest on nonstop flights to the Caribbean from New York, Boston, Philadelphia, Washington, D.C., Chicago, Dallas and Miami, with flight times to some of our favorite islands for the 2026/27 winter season.
A Note on Seasonality
Multiple routes shown below operate only during the peak Caribbean season, with scheduled service beginning in November or even December.
Direct Flights from New York to the Caribbean
Anguilla
- Flight time: 4.5 hours
- Airlines: BermudAir
Antigua
- Flight time: 4.5 hours
- Airlines: American, United
Aruba
- Flight time: 4.5 hours
- Airlines: Delta, JetBlue, United
Bahamas (Nassau)
- Flight time: 3 hours
- Airlines: Delta, JetBlue, United
Barbados
- Flight time: 4.5 hours
- Airlines: American (over the holidays only), JetBlue, United
Dominican Republic (Punta Cana; Puerto Plata)
- Flight time: 3.5 hours
- Airlines: American, Delta, JetBlue, United
Jamaica (Kingston; Montego Bay)
- Flight time: 4 hours
- Airlines: American, Caribbean Airlines, Delta, JetBlue
Puerto Rico (San Juan)
- Flight time: 4 hours
- Airlines: Delta, Frontier (over the holidays only), JetBlue, United
St. Lucia
- Flight time: 4.5 hours
- Airlines: American, JetBlue, United
St. Martin
- Flight time: 4 hours
- Airlines: American, Delta, JetBlue, United
Turks and Caicos (Providenciales)
- Flight time: 3.5 hours
- Airlines: American, BermudAir, Delta, JetBlue, United
U.S. Virgin Islands (Saint Thomas; Saint Croix)
- Flight time: 4 hours
- Airlines: American, Delta, JetBlue, United
Direct Flights from Boston to the Caribbean
Anguilla
- Flight time: 4.5/5 hours
- Airlines: BermudAir
Aruba
- Flight time: 4.5/5 hours
- Airlines: Delta, JetBlue
Bahamas (Nassau)
- Flight time: 3.5 hours
- Airlines: Delta, JetBlue
Barbados
- Flight time: 4.5 hours
- Airlines: JetBlue
Dominican Republic (Punta Cana; Puerto Plata; Santo Domingo)
- Flight time: 4 hours
- Airlines: American, Delta, JetBlue
Jamaica (Montego Bay)
- Flight time: 4 hours
- Airlines: Delta, JetBlue
Puerto Rico (San Juan)
- Flight time: 4 hours
- Airlines: Delta, Frontier, JetBlue
St. Lucia
- Flight time: 4.5 hours
- Airlines: JetBlue
St. Martin
- Flight time: 4 hours
- Airlines: JetBlue
Turks and Caicos (Providenciales)
- Flight time: 3.5 hours
- Airlines: American, BermudAir, Delta, JetBlue
U.S. Virgin Islands (Saint Thomas)
- Flight time: 4 hours
- Airlines: Delta, JetBlue
Direct Flights from Philadelphia to the Caribbean
Aruba
- Flight time: 4.5 hours
- Airlines: American
Bahamas (Nassau)
- Flight time: 3 hours
- Airlines: American
Barbados
- Flight time: 4.5/5 hours
- Airlines: American
Dominican Republic (Punta Cana)
- Flight time: 4 hours
- Airlines: American, Frontier
Jamaica (Montego Bay)
- Flight time: 3.5 hours
- Airlines: American, Frontier (over the holidays only)
Puerto Rico (San Juan)
- Flight time: 4 hours
- Airlines: American, Frontier, JetBlue
St. Lucia
- Flight time: 4.5/5 hours
- Airlines: American
St. Martin
- Flight time: 4/4.5 hours
- Airlines: American
Turks and Caicos (Providenciales)
- Flight time: 3.5 hours
- Airlines: American
U.S. Virgin Islands (Saint Thomas)
- Flight time: 4 hours
- Airlines: American
Direct Flights from Washington, D.C. to the Caribbean
Aruba
- Flight time: 4.5 hours
- Airlines: United
Bahamas (Nassau)
- Flight time: 2.5/3 hours
- Airlines: American, United
Barbados
- Flight time: 4.5/5 hours
- Airlines: United
Dominican Republic (Punta Cana)
- Flight time: 4 hours
- Airlines: United
Jamaica (Montego Bay)
- Flight time: 3.5 hours
- Airlines: United
Puerto Rico (San Juan)
- Flight time: 4 hours
- Airlines: Frontier, JetBlue, United
St. Martin
- Flight time: 4 hours
- Airlines: United
Turks and Caicos (Providenciales)
- Flight time: 3.5 hours
- Airlines: United
U.S. Virgin Islands (Saint Thomas)
- Flight time: 4 hours
- Airlines: United
Direct Flights from Chicago to the Caribbean
Aruba
- Flight time: 5 hours
- Airlines: American, United
Bahamas (Nassau)
- Flight time: 3.5 hours
- Airlines: American, United
Dominican Republic (Punta Cana)
- Flight time: 4.5 hours
- Airlines: American, United
Jamaica (Montego Bay)
- Flight time: 4 hours
- Airlines: American, United
Puerto Rico (San Juan)
- Flight time: 4.5/5 hours
- Airlines: American, Frontier, United
St. Lucia
- Flight time: 5.5/6 hours
- Airlines: United
St. Martin
- Flight time: 5 hours
- Airlines: American, United
Turks and Caicos (Providenciales)
- Flight time: 4 hours
- Airlines: American, United
U.S. Virgin Islands (Saint Thomas)
- Flight time: 4.5/5 hours
- Airlines: American, United
Direct Flights from Dallas to the Caribbean
Aruba
- Flight time: 5 hours
- Airlines: American
Bahamas (Nassau)
- Flight time: 3 hours
- Airlines: American
Dominican Republic (Punta Cana)
- Flight time: 4.5 hours
- Airlines: American
Jamaica (Montego Bay)
- Flight time: 3.5 hours
- Airlines: American
Puerto Rico (San Juan)
- Flight time: 4.5 hours
- Airlines: American, Frontier
Turks and Caicos (Providenciales)
- Flight time: 4 hours
- Airlines: American
U.S. Virgin Islands (Saint Thomas)
- Flight time: 4.5/5 hours
- Airlines: American
Direct Flights from Miami to the Caribbean
Anguilla
- Flight time: 3 hours
- Airlines: American
Antigua
- Flight time: 3 hours
- Airlines: American
Bahamas (Bimini; Freeport; Georgetown; Marsh Harbour; Nassau; North Eleuthera)
- Flight time: ~1 hour
- Airlines: American, Bahamasair
Barbados
- Flight time: 3.5 hours
- Airlines: American
Cuba (Havana)
- Flight time: 1 hour
- Airlines: American, Delta
Dominican Republic (Puerto Plata; Punta Cana; Santo Domingo)
- Flight time: 2 hours
- Airlines: American
Jamaica (Kingston; Montego Bay)
- Flight time: 1.5 hours
- Airlines: American
Puerto Rico (San Juan)
- Flight time: 2.5 hours
- Airlines: American, Frontier
St. Lucia
- Flight time: 3.5 hours
- Airlines: American
Turks and Caicos (Providenciales)
- Flight time: 1.5 hours
- Airlines: American
U.S. Virgin Islands (Saint Thomas; Saint Croix)
- Flight time: 2.5 hours
- Airlines: American
Plus: Seamless Tradewind Aviation Transfers with American, JetBlue and United
Tradewind Aviation, which handles private and scheduled charter flights to islands like Virgin Gorda, Anguilla, Eleuthera, Tortola and St. Barth's (via its fleet of Pilatus PC-12s), partners with American, JetBlue and United, allowing for seamless connections from more than a dozen U.S. airports, including New York's JFK, Boston, Providence, Philadelphia and Washington, D.C.
What About the West Coast?
West Coasters have few fast options in 2026/2027 to reach Caribbean islands. Seasonal nonstops from Los Angeles and Seattle came and went after the routes proved less profitable than airlines hoped, and today Cayman Airways' weekly flight between Los Angeles and Grand Cayman is the only nonstop link between the West Coast and the Caribbean.
Published onOctober 13, 2022
Updated onOctober 4, 2026
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