Portland to The Caribbean Flights

Deals to Puerto Rico are as low as $320 right now.
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Best Deals from PDX to The Caribbean

Discover the cheapest current deals from 416 recent searches matching your trip
  • $343
    San Juan
    5 days in Oct
    Thu
    11
    Tue
    16
  • $320
    San Juan
    12 days in Oct & Nov
    Mon
    22
    Sat
    3
  • $384
    Havana
    7 days in Oct
    Wed
    10
    Wed
    17
  • $462
    Punta Cana
    4 days in Jan
    Sat
    12
    Wed
    16
  • $469
    Nassau
    5 days in Nov
    Sat
    10
    Thu
    15
  • $540
    Oranjestad
    3 days in Sep
    Sat
    15
    Tue
    18
  • When to Fly
    Prices range from $484 in September to $837 in December
  • Puerto Rico
    $320
    This is a great deal at 34% off
  • Cuba
    $384
    This is a good deal at 24% off
  • Dominican Republic
    $462
    This is a great deal at 30% off
  • The Bahamas
    $465
    This is a good deal at 20% off
  • Aruba
    $507
    This is a great deal at 27% off
  • Barbados
    $428
    Nice! This is 43% off
  • From:
    Portland (PDX)
        
    To:
    The Caribbean (77 Airports)    
        
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