New York City, New York to The Caribbean flights

Puerto Rico is typically the cheapest at $340 but deals to Dominican Republic are $186 right now.
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Best Deals from NYC to The Caribbean

Discover the cheapest current deals from 43,667 recent searches matching your trip
  • $269
    Providenciales, Turks and Caicos Islands
    5 days in Nov
    Sat
    9
    Thu
    14
  • $294
    Havana, Cuba
    9 days in Dec
    Sun
    8
    Tue
    17
  • $281
    Punta Cana, Dominican Republic
    5 days in Jan & Feb
    Tue
    28
    Sun
    2
  • $223
    Aguadilla, Puerto Rico
    3 days in Nov
    Fri
    15
    Mon
    18
  • $187
    San Juan, Puerto Rico
    5 days in Nov
    Sat
    16
    Thu
    21
  • $353
    Antigua, Antigua and Barbuda
    5 days in Jan
    Sat
    18
    Thu
    23
  • When to Fly
    Prices range from $342 in January to $642 in September
  • Turks and Caicos Islands
    $269
    This is a great deal at 29% off
  • Cuba
    $271
    This is a great deal at 28% off
  • Dominican Republic
    $186
    Whoa, this is 54% off
  • Puerto Rico
    $187
    Nice! This is 45% off
  • Antigua and Barbuda
    $343
    This is a great deal at 35% off
  • Jamaica
    $366
    This is a great deal at 28% off
  • From:
    New York City, New York (EWR,JFK,LGA)
        
    To:
    The Caribbean (80 Airports)    
        
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