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Caribbean Islands

$129+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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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 November 3, 2025.

This Southwest deal was found by Cheapflights users on 11/2. 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.
Mon 12/15:30 amPDX - SJU
2 stops13h 45mSouthwest
Sat 12/66:15 amSJU - PDX
2 stops14h 15mSouthwest
Deal found 11/2$375
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1112:51 pmPDX - SJU
2 stops31h 05mMultiple Airlines
Thu 12/185:14 pmSJU - PDX
1 stop28h 00mMultiple Airlines
Deal found 11/2$381
This Delta deal was found by Cheapflights users on 11/2. 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 12/95:30 amPDX - SJU
2 stops14h 29mDelta
Tue 12/161:55 pmSJU - PDX
2 stops14h 09mDelta
Deal found 11/2$419
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1112:51 pmPDX - SJU
2 stops31h 05mMultiple Airlines
Sun 12/213:14 pmSJU - PDX
1 stop30h 00mMultiple Airlines
Deal found 11/2$426
This Southwest deal was found by Cheapflights users on 11/2. 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 12/26:15 amPDX - SJU
2 stops11h 50mSouthwest
Tue 12/92:05 pmSJU - PDX
2 stops12h 30mSouthwest
Deal found 11/2$435
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1112:51 pmPDX - SJU
2 stops31h 05mMultiple Airlines
Sat 12/203:14 pmSJU - PDX
1 stop30h 36mMultiple Airlines
Deal found 11/2$439
This Southwest deal was found by Cheapflights users on 11/2. 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 12/38:00 amPDX - SJU
2 stops12h 35mSouthwest
Wed 12/102:05 pmSJU - PDX
2 stops12h 30mSouthwest
Deal found 11/2$444
This Southwest deal was found by Cheapflights users on 11/3. 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 12/28:00 amPDX - SJU
2 stops12h 35mSouthwest
Wed 12/172:05 pmSJU - PDX
2 stops12h 30mSouthwest
Deal found 11/3$457
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1212:55 pmPDX - SJU
2 stops49h 28mMultiple Airlines
Mon 12/225:02 pmSJU - PDX
1 stop28h 12mMultiple Airlines
Deal found 11/2$461
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1212:55 pmPDX - SJU
2 stops30h 30mMultiple Airlines
Thu 12/185:14 pmSJU - PDX
1 stop28h 00mMultiple Airlines
Deal found 11/2$465
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/147:26 pmPDX - SJU
2 stops47h 59mMultiple Airlines
Fri 12/192:52 pmSJU - PDX
1 stop12h 01mMultiple Airlines
Deal found 11/2$477
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/37:29 amPDX - SDQ
1 stop27h 50mMultiple Airlines
Mon 12/154:21 pmSDQ - PDX
2 stops25h 29mMultiple Airlines
Deal found 11/1$507

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 November 3, 2025.

Round-trip from

$375
(Southwest)

One-way from

$129
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$612
From Oregon to Caribbean Islands
Search Deals
One-way flight from Oregon to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($57 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 November 3, 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

Mon 1/26

7:45 am-12:35 am

2 stops13h 50m

San Juan Luis Munoz Marin Intl

Sat 1/31

5:30 am-8:20 pm

2 stops17h 50m

$395

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Sat 1/17

6:50 am-11:00 pm

2 stops13h 10m

San Juan Luis Munoz Marin Intl

Sat 1/31

5:30 am-8:20 pm

2 stops17h 50m

$395

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 12/9

5:30 am-11:59 pm

2 stops14h 29m

San Juan Luis Munoz Marin Intl

Wed 12/17

3:10 pm-10:10 pm

1 stop11h 00m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 1/23

7:00 am-11:44 pm

1 stop12h 44m

San Juan Luis Munoz Marin Intl

Wed 1/28

3:55 pm-10:15 pm

1 stop10h 20m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 1/21

7:00 am-11:59 pm

1 stop12h 59m

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

Tue 12/2

6:15 am-10:05 pm

2 stops11h 50m

San Juan Luis Munoz Marin Intl

Tue 12/9

2:05 pm-10:35 pm

2 stops12h 30m

$435

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 1/23

11:05 pm-12:55 pm

1 stop9h 50m

San Juan Luis Munoz Marin Intl

Tue 1/27

2:05 am-1:45 pm

2 stops15h 40m

$447

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 1/23

11:05 pm-12:55 pm

1 stop9h 50m

San Juan Luis Munoz Marin Intl

Thu 1/29

2:05 am-2:46 pm

2 stops16h 41m

$447

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 1/19

11:05 pm-2:40 pm

1 stop11h 35m

San Juan Luis Munoz Marin Intl

Tue 1/27

2:05 am-12:39 am

2 stops26h 34m

$471

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Sat 3/7

7:00 pm-2:40 pm

2 stops16h 40m

San Juan Luis Munoz Marin Intl

Tue 3/10

1:05 am-3:56 pm

2 stops16h 51m

$485

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

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 $187). Flying from Oregon to Caribbean Islands in December is currently the most expensive (average of $419). 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 November 3, 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 November 18, 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 $447, Southwest can have you in Caribbean Islands from Oregon in 9h 50m. The distance between Oregon and Caribbean Islands is about 3710 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 Frontier, which is currently one of the cheapest options available, starting at $189. United Airlines flights start at $210 while deals on American Airlines start at $210 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 $187). Flying from Oregon to Caribbean Islands in December is currently the most expensive (average of $419). 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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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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$540FlexibilityNo cancel feeOn-time62%
DeltaCheapest$190Average$683FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$248Average$415FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$342Average$687FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$394Average$696FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$431Average$563FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$444Average$725FlexibilityNo cancel feeOn-time63%

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