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Caribbean Islands

$167+ 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 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Mar 7 — Mar 141
Sat 3/7
Sat 3/14
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 February 5, 2026.

This Delta deal was found by Cheapflights users on 2/4. 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.
Mon 5/48:35 pm
BOI
-
SJU
2 stops14h 17m
Delta
Sat 5/91:55 pm
SJU
-
BOI
2 stops11h 45m
Delta
Deal found 2/4$416
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Tue 3/107:00 am
PDX
-
PUJ
1 stop27h 03m
Multiple Airlines
Mon 3/165:39 pm
PUJ
-
PDX
1 stop26h 11m
Multiple Airlines
Deal found 2/1$421
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Tue 3/107:00 am
PDX
-
PUJ
1 stop27h 03m
Multiple Airlines
Tue 3/175:39 pm
PUJ
-
PDX
1 stop26h 11m
Multiple Airlines
Deal found 2/2$423
This Southwest deal was found by Cheapflights users on 2/2. 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 5/46:55 pm
BOI
-
SJU
2 stops13h 40m
Southwest
Mon 5/1810:00 am
SJU
-
BOI
2 stops16h 45m
Southwest
Deal found 2/2$430
This Southwest deal was found by Cheapflights users on 2/2. 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 3/24:15 pm
PDX
-
STT
2 stops18h 40m
Southwest
Mon 3/91:50 pm
STT
-
PDX
2 stops13h 55m
Southwest
Deal found 2/2$432
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/87:00 am
PDX
-
PUJ
1 stop27h 03m
Multiple Airlines
Tue 3/175:39 pm
PUJ
-
PDX
1 stop26h 11m
Multiple Airlines
Deal found 2/2$434
This American Airlines deal was found by Cheapflights users on 2/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/411:48 am
PDX
-
SJU
1 stop13h 36m
American Airlines
Wed 3/111:23 pm
SJU
-
PDX
1 stop13h 21m
American Airlines
Deal found 2/2$436
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Mon 3/93:52 pm
PDX
-
PUJ
2 stops18h 11m
Multiple Airlines
Tue 3/175:39 pm
PUJ
-
PDX
1 stop26h 11m
Multiple Airlines
Deal found 2/2$440
This United Airlines deal was found by Cheapflights users on 2/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/110:16 pm
PDX
-
SJU
1 stop10h 48m
United Airlines
Thu 5/141:40 pm
SJU
-
PDX
1 stop12h 14m
United Airlines
Deal found 2/3$440
This Delta deal was found by Cheapflights users on 2/4. 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 4/2811:35 pm
BOI
-
NAS
1 stop10h 13m
Delta
Tue 5/53:28 pm
NAS
-
BOI
1 stop9h 00m
Delta
Deal found 2/4$444
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/87:00 am
PDX
-
PUJ
1 stop27h 03m
Multiple Airlines
Wed 3/115:39 pm
PUJ
-
PDX
1 stop26h 11m
Multiple Airlines
Deal found 2/2$446
This Southwest deal was found by Cheapflights users on 2/2. 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 4/16:00 am
PDX
-
SJU
2 stops10h 30m
Southwest
Thu 4/302:00 pm
SJU
-
PDX
2 stops13h 10m
Southwest
Deal found 2/2$446

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 February 5, 2026.

Round-trip from

$416
(Southwest)

One-way from

$167
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$578
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 ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 5, 2026.
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

Sat 5/2

5:34 am-11:13 pm

2 stops15h 39m

San Juan Luis Munoz Marin Intl

Sat 5/9

1:55 pm-11:40 pm

2 stops11h 45m

$416

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Mon 3/2

4:15 pm-2:55 pm

2 stops18h 40m

Saint Thomas Island Cyril E King

Mon 3/9

1:50 pm-12:45 am

2 stops13h 55m

$432

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 5/4

10:55 pm-2:44 pm

1 stop12h 49m

San Juan Luis Munoz Marin Intl

Mon 5/11

3:56 pm-11:50 pm

1 stop10h 54m

$440

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 3/3

12:40 am-3:18 pm

1 stop10h 38m

San Juan Luis Munoz Marin Intl

Wed 3/11

7:30 am-8:25 pm

2 stops15h 55m

$440

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 5/11

10:16 pm-12:04 pm

1 stop10h 48m

San Juan Luis Munoz Marin Intl

Fri 5/22

1:00 am-9:21 am

1 stop11h 21m

$440

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 5/1

7:05 pm-12:34 pm

2 stops14h 29m

San Juan Luis Munoz Marin Intl

Thu 5/14

3:56 pm-11:50 pm

1 stop10h 54m

$440

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 5/16

7:40 pm-9:05 am

2 stops10h 25m

San Juan Luis Munoz Marin Intl

Thu 5/21

10:00 am-8:10 pm

2 stops13h 10m

$478

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 3/11

6:30 am-11:15 pm

1 stop13h 45m

San Juan Luis Munoz Marin Intl

Sat 5/2

7:15 am-10:21 pm

2 stops18h 06m

$478

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 5/12

7:00 am-8:38 pm

1 stop10h 38m

San Juan Luis Munoz Marin Intl

Tue 5/19

1:40 pm-9:09 pm

1 stop10h 29m

$478

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 3/2

5:50 am-12:40 am

2 stops14h 50m

San Juan Luis Munoz Marin Intl

Mon 3/9

2:50 pm-12:45 am

2 stops12h 55m

$481

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

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 $188). 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.

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 $416, Delta can have you in Caribbean Islands from Oregon in 13h 40m. 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 JetBlue start at $185 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 $188). 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

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 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 February 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$184Average$680FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$185Average$371FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$241Average$382FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$327Average$724FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$364Average$723FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$438Average$697FlexibilityNo cancel feeOn-time63%

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