Cheap flights from Portland to Caribbean

Travel > Caribbean

Travel tip: Visit Montego Bay on your Holiday.

Check our current prices for flights from Portland to Caribbean. Please note that we also give you historical search data for this city connection. These are all airfares that people found in the past, in order to find more current flight information from Portland to Caribbean, you will need to run a search below.

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From $463 / RT details

Book your flight now with Cheapoair.com and save!

Cheap San Juan airfares from $463/RT are provided by Cheapoair.com. Outbound flight is leaving on 03/02/2025, 10:16 am from Portland Intl (PDX) airport and arrives at San Juan Marin Intl (SJU) at 05:01 pm. The flight time is 6 hours and 45 minutes. The Returning flight departes on 03/11/2025, 12:49 pm (other return dates are also available). Date posted: 04 Jan 2025

Price evolution for flights From Portland To Caribbean

Price overview for flights from Portland to Caribbean

Recent Deals on Flights from Portland to Caribbean:Roundtrip / Oneway

  • $463Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Portland, OR (PDX)San Juan, PR (SJU)03/02/202510:16 am
    San Juan, PR (SJU)Portland, OR (PDX)03/11/202512:49 pm
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  • $504Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Portland, OR (PDX)Montego Bay, JM (MBJ)02/22/202508:28 pm
    Montego Bay, JM (MBJ)Portland, OR (PDX)03/06/202501:07 pm
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  • $626Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Portland, OR (PDX)Punta Cana, DO (PUJ)02/10/202505:30 pm
    Punta Cana, DO (PUJ)Portland, OR (PDX)02/19/202501:39 pm
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  • $667Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Portland, OR (PDX)Punta Cana, DO (PUJ)02/14/202509:18 pm
    Punta Cana, DO (PUJ)Portland, OR (PDX)02/19/202506:10 pm
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  • $738Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Portland, OR (PDX)Punta Cana, DO (PUJ)02/14/202510:16 am
    Punta Cana, DO (PUJ)Portland, OR (PDX)02/20/202504:48 pm
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  • $136Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Portland, OR (PDX)San Juan, PR (SJU)02/25/202508:28 pm
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  • $167Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Portland, OR (PDX)San Juan, PR (SJU)03/08/202507:32 pm
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  • $249Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Portland, OR (PDX)Punta Cana, DO (PUJ)02/18/202510:16 am
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  • $361Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Portland, OR (PDX)Montego Bay, JM (MBJ)04/29/202502:00 pm
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  • $363Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Portland, OR (PDX)Montego Bay, JM (MBJ)03/09/202507:32 pm
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Specify your search details. Browse the cheapest flights from Portland to Caribbean, Caribbean hotel rooms and Portland to Caribbean vacation packages from the most popular providers, airline consolidators and travel search engines.

Know what to do when flying to Caribbean?

Montego Bay Travel Guide The grand dame of island resorts, Montego Bay, though welcoming a great wave of visitors, has saved its own identity. Mo Bay, as it is called, is the most cosmopolitan of Jamaican resorts, its main enticement being the array of luxurious hotels [...]
Montego Bay History Montego Bay is the second city of Jamaica, and the capital of the parish of St. James. This city has a long history, which started with the settlement of the Spanish to Montego Bay after 1510. The reason the Spanish had named the city ‘Bahia [...]
Montego Bay Sightseeing The place to head for complete relaxation for your next vacation is none other than Montego Bay, Jamaica. Montego Bay is a hot tourist spot, and has been such since 1924. And as proof of this increased tourism in Montego Bay, you find a [...]
Montego Bay Nightlife Montego Bay is the place to visit in Jamaica not only for its many places of attraction, but also for its bustling and exciting nightlife. A visit to Montego Bay at night will be an unforgettable one; all you have to do is to go to the Hip [...]
Montego Bay Pictures
  • Jamaica - Montego Bayview
  • Jamaica - Montego Bayview
  • Jamaica - Montego Bayview
  • Jamaica - Montego Bayview
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