If a winter beach escape is on your 2026 vision board, you’re going to want to see this.
According to Dollar Flight Club’s newly released 2026 Caribbean Flight Report, Caribbean flights this winter are the cheapest they’ve been in years, with dozens of roundtrip routes priced $300.
And the data backs it up: after analyzing hundreds of thousands of routes from major U.S. airports, the flight deal experts found widespread price drops for travel between January and April 2026.
The biggest savings? Florida and Northeast routes to Puerto Rico and the Dominican Republic, plus select Southeast, Midwest and Texas departures—many clocking in well below their usual averages.
Related: American Airlines Adds a New Nonstop to One of the Caribbean’s Most Beautiful, Hard-to-Reach Islands
Here are some of the cheapest Caribbean city-pair deals showing up right now:
EWR → San Juan, Puerto Rico—from $116 (Avg. $320), Jan–MarJFK → San Juan, Puerto Rico—from $136 (Avg. $340), Feb–AprFLL → San Juan, Puerto Rico—from $150 (Avg. $330), Jan–MarMCO → St. Thomas, U.S. Virgin Islands—from $152 (Avg. $360), Jan–FebPHL → San Juan, Puerto Rico—from $157 (Avg. $350), Feb–MarDTW → San Juan, Puerto Rico—from $162 (Avg. $370), Jan–MarFLL → Aruba—from $198 (Avg. $400), Feb–AprFLL → Santo Domingo, Dominican Republic—from $200 (Avg. $410), Jan–MarFLL → Montego Bay, Jamaica—from $214 (Avg. $420), Jan–MarEWR → Grenada—from $228 (Avg. $450), Feb–AprPuerto Rico once again stands out as one of the most competitive and affordable Caribbean destinations, with San Juan seeing especially aggressive pricing thanks to heavy airline competition. Meanwhile, Aruba, Jamaica and the Dominican Republic are all delivering strong winter value, with fares running 10–25% lower than last year on key routes.
Related: The 30 Cheapest Places to Fly in 2026, According to New Data
As for timing, Dollar Flight Club recommends booking four to eight weeks before departure, with Tuesday or Wednesday departures still offering the biggest discounts. One caveat: Presidents’ Day week remains the priciest stretch, so flexibility pays.
We’ve highlighted the top routes here, but the full report—including booking strategy, destination breakdowns, and more sub-$300 options—can be found at Dollar Flight Club's 2026 Caribbean Flight Report.
Bottom line? If you’ve been waiting for Caribbean prices to cool off, winter 2026 might be your moment.
Related: The 7 Best Destinations for Women Over 50 to Visit Right Now, According to Travel Advisors
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