A rising trend for many Indagare members—seeking to minimize both their time at airports and their carbon footprints—is to opt for the fewest flight connections as possible. But in the last two years, airlines have reduced their routes, especially to the Caribbean, where getting to many islands already required several flights, drives and even the occasional boat ride.
Here is the latest on non-stop flights to the Caribbean from New York, Boston, Philadelphia, Washington, D.C., Chicago, Dallas and Miami, with flight times to a curated list of some of our favorite Caribbean islands, for travel after November 5, 2022.
Contact your Trip Designer or Indagare, if you are not yet a member, to start planning a trip to the Caribbean. Our team can match you with the accommodations, reservations and activities that are right for you—including reservations at these venues.
Related: Indagare’s Island Matchmaker: The Best Caribbean Islands for Every Traveler
Direct Flights from New York to the Caribbean:
- Aruba: 4.5 hours
- Antigua: 4.5 hours
- Bahamas (Nassau): 3 hours
- Barbados: 4.5 hours
- Dominican Republic (Punta Cana; Puerto Plata): 3.5 hours
- Jamaica (Kingston; Montego Bay): 4 hours
- Puerto Rico (San Juan): 4 hours
- St. Lucia: 4.5 hours
- St. Martin: 4 hours
- Turks and Caicos (Providenciales): 3.5 hours
- U.S. Virgin Islands (Saint Thomas): 4 hours
Direct Flights from Boston to the Caribbean:
- Aruba: 4.5/5 hours
- Bahamas (Nassau): 3.5 hours
- Barbados: 4.5 hours
- Dominican Republic (Punta Cana; Puerto Plata; Santo Domingo): 4 hours
- Jamaica (Montego Bay): 4 hours
- Puerto Rico (San Juan): 4 hours
- St. Lucia: 4.5 hours
- St. Martin: 4 hours
- Turks and Caicos (Providenciales): 3.5 hours
- U.S. Virgin Islands (Saint Thomas): 4 hours
Direct Flights from Philadelphia to the Caribbean:
- Aruba: 4.5 hours
- Dominican Republic (Punta Cana): 4 hours
- Jamaica (Montego Bay): 3.5 hours
- Puerto Rico (San Juan): 4 hours
- Turks and Caicos (Providenciales): 3.5 hours
Direct Flights from Washington, D.C. to the Caribbean:
- Aruba: 4.5 hours
- Bahamas (Nassau): 2.5/3 hours
- Dominican Republic (Punta Cana): 4 hours
- Jamaica (Montego Bay): 3.5 hours
- Puerto Rico (San Juan): 4 hours
- St. Martin: 4 hours
- Turks and Caicos (Providenciales): 3.5 hours
- U.S. Virgin Islands (Saint Thomas: 4 hours
Direct Flights from Chicago to the Caribbean:
- Aruba: 5 hours
- Bahamas (Nassau): 3.5 hours
- Dominican Republic (Punta Cana): 4.5 hours
- Jamaica (Montego Bay): 4 hours
- Puerto Rico (San Juan): 4.5/5 hours
- St. Martin: 5 hours
- Turks and Caicos (Providenciales): 4 hours
- U.S. Virgin Islands (Saint Thomas): 4.5/5 hours
Direct Flights from Dallas to the Caribbean:
- Bahamas (Nassau): 3 hours
- Dominican Republic (Punta Cana): 4.5 hours (available non-stop after November 19)
- Jamaica (Montego Bay): 3.5 hours
- Puerto Rico (San Juan): 4.5 hours
- St. Martin: 5 hours
- Turks and Caicos (Providenciales): 4 hours
- U.S. Virgin Islands (Saint Thomas): 4.5/5 hours
Direct Flights from Miami to the Caribbean:
- Anguilla: 3 hours
- Antigua: 3 hours
- Bahamas (Freeport; Georgetown; Marsh Harbour; Nassau; North Eleuthera): ~1 hour
- Barbados: 3.5 hours
- Cuba (Havana): 1 hour
- Dominican Republic (Puerto Plata; Punta Cana; Santo Domingo): 2 hours
- Jamaica (Kingston; Montego Bay): 1.5 hours
- Puerto Rico (San Juan): 2.5 hours
- St. Lucia: 3.5 hours
- Turks and Caicos: 1.5 hours
- U.S. Virgin Islands (Saint Thomas; Saint Croix): 2.5 hours
Some of our most beloved islands, like Mustique and St. Barth’s, aren’t reachable by non-stop commercial flight. One workaround? Consider taking a private charter flight.
Contact your Trip Designer or Indagare, if you are not yet a member, to start planning a trip to the Caribbean. Our team can match you with the accommodations, reservations and activities that are right for you—including reservations at these venues.