A new report from Dollar Flight Club found flights to the Caribbean this winter are cheaper than they’ve been in years. The report looked at airfare between major U.S. airports and Caribbean destinations, for travel between January and April 2026, contrasting those fares against long-term patterns.
One of the standout destinations? San Juan, Puerto Rico. Right now, travelers can head to San Juan from multiple major U.S. hubs, including Newark (EWR), New York City (JFK), Fort Lauderdale (FLL), Philadelphia (PHL) and Detroit (DTW) at fares averaging around $300–350, though flights start as low as $116.
Other destinations proving budget-friendly this winter? Flights to Nassau are starting at around $240, compared to the $460 average from last year around this time. Similar fare differences can be seen in flights to Jamaica, the Dominican Republic, Aruba, Barbados and St. Lucia.
Dollar Flight Club advises, if you are going to take advantage of some of these seasonal deals, to attempt to book your flight four–eight weeks out. Additionally, the brand noted travelers can see significant savings by booking a Tuesday or Wednesday departure with a Saturday return, as opposed to a weekend roundtrip.
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