These Are the Most Affordable Flights to the Caribbean This Winter—With Roundtrip Rates Starting at $116

Cold weather spikes may have travelers dreaming of a Caribbean getaway. And this year, airfare to the region is actually cheaper than it has been in years.

That’s according to the Dollar Flight Club, which found dozens of roundtrip routes for under $300 from major cities like New York, Fort Lauderdale, Detroit, and more. These deals include jaunts to popular islands like Puerto Rico, St. Thomas in the U.S. Virgin Islands, Aruba, and beyond.

“Airfare to the Caribbean is trending lower than it has in years and not just a little,” Dollar Flight Club wrote in its report, adding travelers planning an island getaway this winter should consider purchasing their tickets about four to eight weeks before their planned departure. Outbound flights on Tuesdays and Wednesday and return flights on Saturdays can also result in a savings of about 12 to 25 percent compared to weekend roundtrips.

To come up with the winter season’s most affordable flights, the company said it analyzed hundreds of thousands of airfare data points from major airports in the United States to popular Caribbean spots between January and April 2026.

However, timing matters. Dollar Flight Club noted the holiday week of Presidents’ Day (from Feb. 14 to 21) “remains the one stretch where prices consistently spike.”

The inexpensive flights also come on the heels of the temporary closure of airspace in the Caribbean following U.S. military action in Venezuela earlier this month, leading many travelers to scramble to get home. However, while some destinations in the region are classified under the State Department’s highest travel warning, like Venezuela and Haiti, others are considered exceptionally safe from Antigua and Barbuda to Aruba, Barbados, the Cayman Islands, Dominica, Saint Lucia, and beyond.

These are the 10 cheapest flights travelers can score for the winter season, and when to go, according to Dollar Flight Club.

1. Newark Liberty International Airport (EWR) to Puerto Rico’s Luis Munoz Marin International Airport (SJU)
   Rates starting at $116; average price previously $320
   When to go: January to March
2. New York’s John F. Kennedy International Airport (JFK) to SJU
   Rates starting at $136; average price previously $340
   When to go: February to April
3. Fort Lauderdale-Hollywood International Airport (FLL) to SJU
   Rates starting at $150; average price previously $330
   When to go: January to March
4. Orlando International Airport (MCO) to St. Thomas’ Cyril E. King Airport (STT)
   Rates starting at $152; average price previously $360
   When to go: January to February
5. Philadelphia International Airport (PHL) to SJU
   Rates starting at $157; average price previously $350
   When to go: February to March
6. Detroit Metropolitan Wayne County Airport (DTW) to SJU
   Rates starting at $162; average price previously $370
   When to go: January to March
7. FLL to Aruba’s Queen Beatrix International Airport (AUA)
   Rates starting at $198; average price previously $400
   When to go: February to April
8. FLL to the Dominican Republic’s Las Américas International Airport (SDQ) near Santo Domingo
   Rates starting at $200; average price previously $410
   When to go: January to March
9. FLL to Jamaica’s Sangster International Airport (MBJ) in Montego Bay
   Rates starting at $214; average price previously $420
   When to go: January to March
10. EWR to Grenada’s Maurice Bishop International Airport (GND)
    Rates starting at $228; average price previously $450
    When to go: February to April