Portland, Oregon to The Caribbean flights

Deals to Puerto Rico are as low as $344 right now.
Not ready to book?
Download Hopper to watch.

Best Deals from PDX to The Caribbean

Discover the cheapest current deals from 389 recent searches matching your trip
  • $347
    San Juan
    5 days in Jan
    Sat
    26
    Thu
    31
  • $344
    San Juan
    8 days in Jan & Feb
    Tue
    29
    Wed
    6
  • $587
    Nassau
    10 days in Nov
    Tue
    6
    Fri
    16
  • $523
    Oranjestad
    5 days in Jan
    Sun
    6
    Fri
    11
  • $642
    Nassau
    6 days in Jun
    Fri
    14
    Thu
    20
  • $597
    Oranjestad
    8 days in Nov
    Thu
    22
    Fri
    30
  • When to Fly
    Prices range from $524 in January to $868 in December
  • Puerto Rico
    $344
    Nice! This is 42% off
  • The Bahamas
    $587
    This is the best available price
  • Aruba
    $523
    This is a good deal at 21% off
  • United States Virgin Islands
    $406
    Whoa, this is 50% off
  • Barbados
    $767
    This is a good deal at 13% off
  • Turks and Caicos Islands
    $875
    This is the best available price
  • From:
    Portland, Oregon (PDX)
        
    To:
    The Caribbean (77 Airports)    
        
    Apply Changes