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$144+ Cheap flights from Oregon to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/4. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Oregon to Caribbean

Cheapest flights from Oregon to Caribbean
Explore the most affordable flight options available from Oregon to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This American Airlines deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1311:59 pmPDX - MBJ
2 stops11h 13mAmerican Airlines
Fri 12/194:11 pmMBJ - PDX
1 stop11h 48mAmerican Airlines
Deal found 12/11$545
This American Airlines deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1410:15 pmPDX - MBJ
1 stop12h 11mAmerican Airlines
Fri 12/1911:07 amMBJ - PDX
1 stop16h 52mAmerican Airlines
Deal found 12/11$553
This American Airlines deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1010:45 pmPDX - MBJ
1 stop12h 27mAmerican Airlines
Wed 12/172:02 pmMBJ - PDX
1 stop12h 50mAmerican Airlines
Deal found 12/10$583
This American Airlines deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1310:15 pmPDX - MBJ
1 stop8h 57mAmerican Airlines
Sun 12/211:22 pmMBJ - PDX
1 stop10h 57mAmerican Airlines
Deal found 12/11$588
This eDestinos deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/198:45 pmPDX - SJU
3 stops48h 39mMultiple Airlines
Fri 1/97:10 amSJU - PDX
3 stops43h 36mMultiple Airlines
Deal found 12/10$593
This Delta deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/135:30 pmPDX - MBJ
2 stops16h 34mDelta
Sun 12/218:00 amMBJ - PDX
2 stops16h 56mDelta
Deal found 12/10$618
This United Airlines deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1011:19 pmPDX - NAS
1 stop11h 29mUnited Airlines
Fri 12/122:35 pmNAS - PDX
1 stop11h 22mUnited Airlines
Deal found 12/10$625
This Delta deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1011:20 pmPDX - MBJ
2 stops11h 53mDelta
Wed 12/172:29 pmMBJ - PDX
2 stops12h 35mDelta
Deal found 12/10$645
This American Airlines deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1310:15 pmPDX - SJU
1 stop12h 00mAmerican Airlines
Sat 12/2010:25 amSJU - PDX
1 stop18h 34mAmerican Airlines
Deal found 12/10$655
This American Airlines deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1310:15 pmPDX - NAS
1 stop12h 44mAmerican Airlines
Tue 12/236:45 pmNAS - PDX
1 stop9h 14mAmerican Airlines
Deal found 12/11$705
This American Airlines deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/123:15 pmPDX - SJU
2 stops14h 54mAmerican Airlines
Fri 12/194:38 pmSJU - PDX
2 stops13h 00mAmerican Airlines
Deal found 12/11$715
This Delta deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/135:15 pmPDX - NAS
2 stops15h 26mDelta
Tue 12/238:10 amNAS - PDX
2 stops16h 49mDelta
Deal found 12/11$719

Find flight deals from Oregon to Caribbean

Keep the following information in mind while searching for Oregon to Caribbean flight deals. Data was last updated December 12, 2025.

Round-trip from

$369
(Southwest)

One-way from

$144
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$769
From Oregon to Caribbean
Search Deals
One-way flight from Oregon to Caribbean
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($68 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Oregon to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 12, 2025.
Use the filters below to find and compare flights from Oregon to Caribbean that are best for you.

Fly from

Oregon

Fly to

Caribbean

Route

Depart

Return

Price

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Tue 2/3

7:45 am-12:35 am

2 stops13h 50m

San Juan Luis Munoz Marin Intl

Tue 2/10

12:10 pm-10:30 pm

2 stops13h 20m

$395

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Mon 2/2

6:20 pm-1:05 pm

2 stops15h 45m

San Juan Luis Munoz Marin Intl

Fri 2/6

7:30 am-11:59 pm

2 stops19h 29m

$405

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Mon 2/2

7:45 am-11:10 pm

2 stops12h 25m

San Juan Luis Munoz Marin Intl

Fri 2/6

5:35 am-3:50 pm

2 stops13h 15m

$405

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 2/2

7:00 am-9:00 pm

1 stop10h 00m

San Juan Luis Munoz Marin Intl

Thu 2/5

2:15 pm-9:49 pm

1 stop11h 34m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 1/13

7:00 am-9:26 pm

1 stop10h 26m

San Juan Luis Munoz Marin Intl

Wed 2/4

3:46 pm-10:53 pm

1 stop11h 07m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 2/1

1:24 pm-6:11 am

2 stops12h 47m

San Juan Luis Munoz Marin Intl

Tue 2/10

3:46 pm-10:53 pm

1 stop11h 07m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 1/24

9:45 pm-1:06 pm

1 stop11h 21m

San Juan Luis Munoz Marin Intl

Tue 2/3

2:15 pm-10:15 pm

1 stop12h 00m

$429

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 1/25

6:50 am-11:45 pm

1 stop12h 55m

San Juan Luis Munoz Marin Intl

Fri 2/6

3:20 pm-12:17 am

2 stops12h 57m

$429

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 1/23

9:45 pm-1:05 pm

1 stop11h 20m

San Juan Luis Munoz Marin Intl

Tue 2/3

2:15 pm-10:15 pm

1 stop12h 00m

$429

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 1/23

9:45 pm-1:05 pm

1 stop11h 20m

San Juan Luis Munoz Marin Intl

Fri 2/6

7:30 am-8:59 pm

2 stops17h 29m

$429

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 60 results
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Best time to book a flight from Oregon to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Oregon with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Oregon to Caribbean

What is the cheapest month to book a flight from Oregon to Caribbean?

Currently, August is the cheapest month in which you can book a flight from Oregon to Caribbean (average of $186). Flying from Oregon to Caribbean in November is currently the most expensive (average of $399). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from OR to CB?

Find hourly flight availability from Oregon to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 12, 2025.

It’s typically best to fly out from Oregon to Caribbean at noon. Doing so could potentially save you 23% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly from Oregon to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Oregon to Caribbean. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Oregon to Caribbean flight should consider departing on Sunday afternoons when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Related info for your journey

Find useful and relevant information for your journey from Oregon to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Oregon to Caribbean?

    Departing from Oregon to Caribbean will take you 10h. There are 3710 mi between Oregon and Caribbean. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Oregon to Caribbean one-way?

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $143. Users have also found prices from $150 and $174 on Delta and United Airlines, respectively.

  • Can I find deals for flights from Oregon to Caribbean that include hotel bookings?

    Yes. In addition to deals on Oregon to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oregon to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oregon to Caribbean.

  • Can I find deals for business class flights from Oregon to Caribbean?

    Yes. Cheapflights offers flight deals from Oregon to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Oregon to Caribbean?

    Currently, August is the cheapest month in which you can book a flight from Oregon to Caribbean (average of $186). Flying from Oregon to Caribbean in November is currently the most expensive (average of $399). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Oregon to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Oregon to Caribbean

Discover the top 6 airlines that operate flights from Oregon to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$540FlexibilityNo cancel feeOn-time62%
DeltaCheapest$190Average$703FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$243Average$330FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$347Average$709FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$399Average$718FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$444Average$725FlexibilityNo cancel feeOn-time63%

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