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Caribbean Islands

$193+ 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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
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Cheap 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 septiembre 16, 2025.

Round-trip from

$373
(Frontier)

One-way from

$193
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$481
From Oregon to Caribbean Islands
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One-way flight from Oregon to Caribbean Islands
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Highest demand for flights based on searches. 6% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 septiembre 16, 2025.

This Frontier deal was found by Cheapflights users on 9/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/1312:52 pmPDX - SJU
2 stops23h 18mFrontier
dom. 11/162:11 amSJU - PDX
2 stops13h 45mFrontier
Deal found 9/13$373
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/3012:52 pmPDX - SJU
2 stops24h 18mFrontier
mié. 11/51:59 amSJU - PDX
2 stops13h 57mFrontier
Deal found 9/15$384
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/2812:52 pmPDX - SJU
2 stops19h 27mFrontier
vie. 11/710:39 pmSJU - PDX
2 stops17h 17mFrontier
Deal found 9/15$390
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/2412:43 pmPDX - SJU
2 stops20h 33mFrontier
vie. 11/72:11 amSJU - PDX
2 stops13h 45mFrontier
Deal found 9/14$391
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/266:15 amBOI - SJU
1 stop9h 10mUnited Airlines
mié. 10/291:05 amSJU - BOI
2 stops14h 39mUnited Airlines
Deal found 9/16$395
This Frontier deal was found by Cheapflights users on 9/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/2812:52 pmPDX - SJU
2 stops19h 27mFrontier
dom. 11/22:03 amSJU - PDX
2 stops13h 53mFrontier
Deal found 9/16$406
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/278:02 amPDX - SJU
2 stops22h 50mFrontier
lun. 9/299:07 amSJU - PDX
2 stops18h 05mFrontier
Deal found 9/14$413
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/127:10 pmPDX - SJU
2 stops13h 39mUnited Airlines
mar. 11/182:25 pmSJU - PDX
1 stop11h 01mUnited Airlines
Deal found 9/16$419
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/247:15 amPDX - SJU
2 stops23h 37mFrontier
lun. 9/299:07 amSJU - PDX
2 stops18h 05mFrontier
Deal found 9/14$425
This American Airlines deal was found by Cheapflights users on 9/14. 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.
mié. 10/296:40 amBOI - SJU
2 stops13h 30mAmerican Airlines
mar. 11/47:15 amSJU - BOI
1 stop18h 17mAmerican Airlines
Deal found 9/14$431
This Southwest deal was found by Cheapflights users on 9/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/126:15 amPDX - SJU
2 stops13h 05mSouthwest
mar. 11/188:55 amSJU - PDX
2 stops13h 20mSouthwest
Deal found 9/15$450
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/315:00 amPDX - PUJ
1 stop9h 18mUnited Airlines
vie. 11/72:55 pmPUJ - PDX
1 stop11h 38mUnited Airlines
Deal found 9/16$455

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 septiembre 16, 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

mié. 10/29

5:25 am-11:56 pm

2 stops16h 31m

San Juan Luis Munoz Marin Intl

mar. 11/4

7:15 am-5:13 pm

2 stops12h 58m

$395

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

dom. 10/26

6:15 am-5:25 pm

1 stop9h 10m

San Juan Luis Munoz Marin Intl

mié. 10/29

1:05 am-1:44 pm

2 stops14h 39m

$395

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

sáb. 1/24

6:00 pm-4:51 pm

2 stops19h 51m

San Juan Luis Munoz Marin Intl

mié. 2/25

4:25 pm-11:42 pm

1 stop10h 17m

$395

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

sáb. 12/6

11:59 pm-3:40 pm

1 stop11h 41m

San Juan Luis Munoz Marin Intl

vie. 12/12

2:25 pm-9:15 pm

1 stop10h 50m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

vie. 11/7

5:25 pm-3:11 pm

2 stops17h 46m

San Juan Luis Munoz Marin Intl

vie. 11/14

3:20 pm-10:05 pm

1 stop10h 45m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

jue. 10/30

6:00 am-9:59 pm

1 stop12h 59m

San Juan Luis Munoz Marin Intl

jue. 11/6

7:15 am-1:00 pm

1 stop9h 45m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

sáb. 10/11

10:32 pm-1:45 pm

1 stop12h 13m

San Juan Luis Munoz Marin Intl

vie. 10/17

1:05 am-11:41 am

2 stops13h 36m

$451

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

vie. 10/31

5:00 am-5:18 pm

1 stop9h 18m

Punta Cana

vie. 11/7

2:55 pm-10:33 pm

1 stop11h 38m

$455

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

mié. 10/29

7:38 pm-11:59 am

2 stops13h 21m

Punta Cana

mié. 11/5

2:05 pm-9:26 pm

1 stop11h 21m

$459

PortlandSantiago de los Caballeros

PDX - STI

PDXSTI

Portland

lun. 3/9

7:00 am-11:27 pm

1 stop13h 27m

Santiago de los Caballeros

mié. 3/11

6:00 am-9:35 pm

1 stop18h 35m

$467

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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, September is the cheapest month in which you can book a flight from Oregon to Caribbean Islands (average of $254). Flying from Oregon to Caribbean Islands in June is currently the most expensive (average of $339). 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 septiembre 16, 2025.

When flying from Oregon to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 10m. 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 Delta, which is currently one of the cheapest options available, starting at $210. American Airlines flights start at $229 while deals on Air Canada start at $293 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, September is the cheapest month in which you can book a flight from Oregon to Caribbean Islands (average of $254). Flying from Oregon to Caribbean Islands in June is currently the most expensive (average of $339). 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

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Oregon to Caribbean Islands

Discover the top 7 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 septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$540FlexibilityNo cancel feeOn-time62%
DeltaCheapest$190Average$672FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$248Average$415FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$341Average$698FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$394Average$720FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$450Average$729FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$454Average$591FlexibilityNo cancel feeOn-time75%

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