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.
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.
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–AprRelated: The 30 Cheapest Places to Fly in 2026, According to New Data
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.
Related: The 7 Best Destinations for Women Over 50 to Visit Right Now, According to Travel Advisors
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