New York City, New York to The Caribbean flights

Deals to Puerto Rico are as low as $127 right now.
Not ready to book?
Download Hopper to watch.

Best Deals from NYC to The Caribbean

Discover the cheapest current deals from 67,885 recent searches matching your trip
  • $274
    Providenciales, Turks and Caicos Islands
    3 days in Mar
    Fri
    6
    Mon
    9
  • $127
    San Juan, Puerto Rico
    2 days in Dec
    Fri
    6
    Sun
    8
  • $127
    San Juan, Puerto Rico
    2 days in Jan
    Sat
    25
    Mon
    27
  • $274
    Providenciales, Turks and Caicos Islands
    5 days in Feb & Mar
    Fri
    28
    Wed
    4
  • $309
    Antigua, Antigua and Barbuda
    5 days in Jan & Feb
    Thu
    30
    Tue
    4
  • $244
    Havana, Cuba
    4 days in Jan
    Thu
    23
    Mon
    27
  • When to Fly
    Prices range from $325 in January to $584 in December
  • Turks and Caicos Islands
    $269
    This is a great deal at 38% off
  • Puerto Rico
    $127
    Whoa, this is 61% off
  • Antigua and Barbuda
    $309
    Nice! This is 42% off
  • Cuba
    $244
    Nice! This is 43% off
  • Cayman Islands
    $272
    This is a great deal at 34% off
  • Jamaica
    $332
    This is a great deal at 36% off
  • From:
    New York City, New York (EWR,JFK,LGA)
        
    To:
    The Caribbean (80 Airports)    
        
    Apply Changes