New York City, New York to The Caribbean flights

Puerto Rico is typically the cheapest at $323 but deals to Dominican Republic are $198 right now.
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Best Deals from NYC to The Caribbean

Discover the cheapest current deals from 17,524 recent searches matching your trip
  • $269
    Providenciales, Turks and Caicos Islands
    7 days in Sep & Oct
    Sat
    28
    Sat
    5
  • $246
    Havana, Cuba
    2 days in Oct
    Sat
    12
    Mon
    14
  • $238
    Aguadilla, Puerto Rico
    4 days in Oct
    Fri
    18
    Tue
    22
  • $323
    Port of Spain, Trinidad and Tobago
    3 days in Sep
    Thu
    5
    Sun
    8
  • $242
    San Juan, Puerto Rico
    3 days in Oct
    Fri
    18
    Mon
    21
  • $419
    Montego Bay, Jamaica
    4 days in Sep
    Wed
    25
    Sun
    29
  • When to Fly
    Prices range from $324 in September to $613 in December
  • Turks and Caicos Islands
    $269
    This is a great deal at 35% off
  • Cuba
    $246
    This is a great deal at 25% off
  • Puerto Rico
    $223
    This is a great deal at 31% off
  • Trinidad and Tobago
    $323
    This is a great deal at 30% off
  • Jamaica
    $348
    This is a great deal at 32% off
  • The Bahamas
    $299
    This is a great deal at 30% off
  • From:
    New York City, New York (EWR,JFK,LGA)
        
    To:
    The Caribbean (80 Airports)    
        
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