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Caribbean Islands

$155+ Cheap flights from Oregon to Caribbean Islands

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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Oregon to Caribbean Islands

Cheapest flights from Oregon to Caribbean Islands
Explore the most affordable flight options available from Oregon to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This Gotogate deal was found by Cheapflights users on 12/17. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/307:00 pmPDX - PUJ
2 stops15h 00mAir Canada
Tue 1/610:35 pmPUJ - PDX
2 stops20h 05mAir Canada
Deal found 12/17$693
This eDestinos deal was found by Cheapflights users on 12/15. 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 stops25h 54mMultiple Airlines
Sat 1/107:11 pmSJU - PDX
3 stops46h 37mMultiple Airlines
Deal found 12/15$723
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/3110:49 pmPDX - SJU
1 stop18h 22mAmerican Airlines
Tue 1/61:31 pmSJU - PDX
1 stop14h 15mAmerican Airlines
Deal found 12/16$745
This Southwest deal was found by Cheapflights users on 12/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:00 amPDX - SJU
2 stops13h 05mSouthwest
Tue 1/66:10 amSJU - PDX
2 stops13h 30mSouthwest
Deal found 12/16$755
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Thu 12/1811:21 pmPDX - SJU
1 stop10h 25mAmerican Airlines
Mon 1/196:00 amSJU - PDX
1 stop21h 46mAmerican Airlines
Deal found 12/17$795
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Mon 12/226:27 pmPDX - AUA
2 stops18h 23mUnited Airlines
Wed 12/313:25 pmAUA - PDX
1 stop11h 34mUnited Airlines
Deal found 12/17$826
This Southwest deal was found by Cheapflights users on 12/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/166:55 pmPDX - SJU
2 stops11h 30mSouthwest
Wed 12/172:05 pmSJU - PDX
2 stops12h 30mSouthwest
Deal found 12/16$840
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Mon 12/2210:49 pmPDX - AUA
1 stop14h 05mAmerican Airlines
Wed 12/315:55 pmAUA - PDX
1 stop11h 04mAmerican Airlines
Deal found 12/17$851
This Delta deal was found by Cheapflights users on 12/17. 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.
Tue 12/3010:05 pmPDX - PUJ
1 stop10h 36mDelta
Tue 1/63:21 pmPUJ - PDX
2 stops23h 13mDelta
Deal found 12/17$854
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/1710:45 pmPDX - STT
1 stop14h 54mAmerican Airlines
Wed 12/244:25 pmSTT - PDX
2 stops24h 25mAmerican Airlines
Deal found 12/16$865
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/2410:39 pmPDX - SJU
1 stop15h 27mAmerican Airlines
Wed 12/3110:25 amSJU - PDX
1 stop18h 34mAmerican Airlines
Deal found 12/17$870
This American Airlines deal was found by Cheapflights users on 12/15. 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.
Thu 12/255:33 amPDX - SJU
1 stop13h 49mAmerican Airlines
Tue 1/64:49 pmSJU - PDX
1 stop10h 57mAmerican Airlines
Deal found 12/15$875

Find flight deals from Oregon to Caribbean Islands

Keep the following information in mind while searching for Oregon to Caribbean Islands flight deals. Data was last updated December 18, 2025.

Round-trip from

$395
(Southwest)

One-way from

$155
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$781
From Oregon to Caribbean Islands
Search Deals
One-way flight from Oregon to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($76 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oregon to Caribbean Islands 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 18, 2025.
Use the filters below to find and compare flights from Oregon to Caribbean Islands that are best for you.

Fly from

Oregon

Fly to

Caribbean Islands

Route

Depart

Return

Price

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Wed 2/25

5:40 am-11:56 pm

2 stops15h 16m

San Juan Luis Munoz Marin Intl

Wed 3/4

6:15 am-8:55 pm

2 stops17h 40m

$395

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Mon 1/26

6:10 am-6:25 pm

1 stop9h 15m

San Juan Luis Munoz Marin Intl

Tue 2/3

8:10 am-9:52 pm

2 stops16h 42m

$395

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 2/1

6:22 pm-10:48 am

2 stops12h 26m

San Juan Luis Munoz Marin Intl

Thu 3/12

3:03 pm-12:50 am

1 stop12h 47m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 4/29

11:10 pm-1:45 pm

1 stop11h 35m

San Juan Luis Munoz Marin Intl

Fri 5/8

1:00 am-11:35 am

2 stops13h 35m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 1/27

6:50 am-8:58 pm

1 stop10h 08m

San Juan Luis Munoz Marin Intl

Tue 2/3

3:55 pm-10:15 pm

1 stop10h 20m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 3/6

10:55 pm-9:33 pm

1 stop18h 38m

San Juan Luis Munoz Marin Intl

Fri 3/13

3:36 pm-11:44 pm

1 stop11h 08m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 1/17

11:05 pm-2:40 pm

1 stop11h 35m

San Juan Luis Munoz Marin Intl

Sat 1/24

7:45 am-6:55 pm

2 stops15h 10m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 1/19

7:37 pm-2:10 pm

2 stops14h 33m

San Juan Luis Munoz Marin Intl

Wed 1/28

7:00 am-5:35 pm

2 stops14h 35m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 1/19

11:05 pm-2:40 pm

1 stop11h 35m

San Juan Luis Munoz Marin Intl

Wed 1/28

2:15 pm-9:49 pm

1 stop11h 34m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 1/28

5:15 pm-2:10 pm

2 stops16h 55m

San Juan Luis Munoz Marin Intl

Wed 2/4

7:00 am-5:35 pm

2 stops14h 35m

$419

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

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

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands

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

Currently, August is the cheapest month in which you can book a flight from Oregon to Caribbean Islands (average of $186). Flying from Oregon to Caribbean Islands 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 EPX?

Find hourly flight availability from Oregon to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 23% on flights from Oregon to Caribbean Islands by exploring options for tickets at noon.

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

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

Travelers seeking maximum savings on their Oregon to Caribbean Islands 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 Islands. 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 Islands?

    For as low as $395, Delta can have you in Caribbean Islands from Oregon in 9h 15m. The distance between Oregon and Caribbean Islands is about 3374 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $143. Delta flights start at $150 while deals on United Airlines start at $174 one-way.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Oregon to Caribbean Islands 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 Islands?

    Currently, August is the cheapest month in which you can book a flight from Oregon to Caribbean Islands (average of $186). Flying from Oregon to Caribbean Islands 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 Islands

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Top 6 airlines flying from Oregon to Caribbean Islands

Discover the top 6 airlines that operate flights from Oregon to Caribbean Islands. 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 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$540FlexibilityNo cancel feeOn-time62%
DeltaCheapest$190Average$710FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$243Average$358FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$348Average$712FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$402Average$706FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$444Average$726FlexibilityNo cancel feeOn-time63%

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