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

""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."

"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."

Dozens of roundtrip routes from major U.S. cities to Caribbean islands are available for under $300, including Puerto Rico, St. Thomas, Aruba, and other popular destinations. Airfare to the Caribbean is at multiyear lows, with the most affordable winter-season fares found for travel between January and April 2026. Purchasing tickets about four to eight weeks before departure can yield savings, and choosing outbound flights on Tuesdays or Wednesdays with Saturday returns can reduce costs by roughly 12–25 percent. Prices consistently spike during Presidents' Day week (Feb. 14–21). Recent temporary Caribbean airspace closures after U.S. military action in Venezuela caused travel disruptions, and some countries carry high State Department travel warnings while many islands remain exceptionally safe.

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