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$152+ 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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This Delta deal was found by Cheapflights users on 1/28. 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 10/274:05 pm
BOI
-
SJU
2 stops17h 51m
Delta
Sat 10/317:30 am
SJU
-
BOI
2 stops14h 47m
Delta
Deal found 1/28$416
This Southwest deal was found by Cheapflights users on 1/28. 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.
Thu 5/74:20 pm
BOI
-
SJU
2 stops14h 50m
Southwest
Tue 5/125:05 am
SJU
-
BOI
2 stops15h 55m
Southwest
Deal found 1/28$444
This Delta deal was found by Cheapflights users on 1/28. 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.
Sun 5/1011:30 pm
BOI
-
NAS
1 stop12h 16m
Delta
Fri 5/153:03 pm
NAS
-
BOI
1 stop9h 35m
Delta
Deal found 1/28$444
This Delta deal was found by Cheapflights users on 1/28. 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 5/117:30 pm
BOI
-
NAS
2 stops14h 07m
Delta
Fri 5/151:12 pm
NAS
-
BOI
2 stops11h 52m
Delta
Deal found 1/28$448
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Tue 4/2111:40 pm
PDX
-
SJU
1 stop20h 21m
American Airlines
Mon 5/411:59 pm
SJU
-
PDX
1 stop20h 00m
American Airlines
Deal found 1/27$451
This American Airlines deal was found by Cheapflights users on 1/28. 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 2/257:00 am
BOI
-
SJU
1 stop13h 31m
American Airlines
Wed 3/47:00 am
SJU
-
BOI
2 stops18h 22m
American Airlines
Deal found 1/28$452
This Southwest deal was found by Cheapflights users on 1/28. 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 2/238:35 am
PDX
-
SJU
2 stops12h 05m
Southwest
Fri 2/276:00 am
SJU
-
PDX
2 stops12h 55m
Southwest
Deal found 1/28$461
This United Airlines deal was found by Cheapflights users on 1/28. 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.
Sun 5/2410:00 am
PDX
-
SJU
1 stop10h 50m
United Airlines
Fri 5/291:00 am
SJU
-
PDX
2 stops13h 38m
United Airlines
Deal found 1/28$468
This Southwest deal was found by Cheapflights users on 1/28. 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 9/2111:30 pm
PDX
-
SJU
2 stops11h 05m
Southwest
Mon 9/286:00 am
SJU
-
PDX
2 stops13h 35m
Southwest
Deal found 1/28$469
This Southwest deal was found by Cheapflights users on 1/28. 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 3/108:40 am
PDX
-
SJU
2 stops12h 35m
Southwest
Tue 3/1710:10 am
SJU
-
PDX
2 stops16h 00m
Southwest
Deal found 1/28$470
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 4/77:03 am
PDX
-
PUJ
1 stop25h 17m
Multiple Airlines
Thu 4/167:30 pm
PUJ
-
PDX
2 stops18h 06m
Multiple Airlines
Deal found 1/28$478
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Tue 3/3111:59 pm
PDX
-
SJU
2 stops12h 29m
American Airlines
Sun 4/57:11 am
SJU
-
PDX
1 stop20h 11m
American Airlines
Deal found 1/27$478

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 January 29, 2026.

Round-trip from

$416
(Delta)

One-way from

$152
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$554
From Oregon to Caribbean
Search Deals
One-way flight from Oregon to Caribbean
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 January 2026
Search Deals

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 January 29, 2026.
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

Thu 5/7

6:30 am-5:38 pm

1 stop9h 08m

San Juan Luis Munoz Marin Intl

Tue 5/12

7:20 am-9:17 pm

2 stops15h 57m

$416

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Wed 2/25

5:20 am-11:58 pm

2 stops15h 38m

San Juan Luis Munoz Marin Intl

Wed 3/4

7:30 am-8:55 pm

2 stops16h 25m

$416

BoiseNassau

BOI - NAS

BOINAS

Boise Air Term. Gowen Fld

Sun 5/10

11:30 pm-1:46 pm

1 stop12h 16m

Nassau Intl

Fri 5/15

3:03 pm-10:38 pm

1 stop9h 35m

$444

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Fri 4/10

4:20 pm-8:55 am

2 stops14h 35m

San Juan Luis Munoz Marin Intl

Fri 4/17

6:50 am-5:00 pm

2 stops12h 10m

$488

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 3/23

11:55 pm-2:45 pm

2 stops11h 50m

San Juan Luis Munoz Marin Intl

Wed 4/1

5:55 am-4:50 pm

2 stops13h 55m

$493

BoiseNassau

BOI - NAS

BOINAS

Boise Air Term. Gowen Fld

Wed 2/25

6:55 pm-3:22 pm

2 stops18h 27m

Nassau Intl

Wed 3/4

3:35 pm-10:06 am

2 stops20h 31m

$501

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 2/26

12:40 am-9:12 pm

2 stops16h 32m

San Juan Luis Munoz Marin Intl

Tue 3/10

6:15 am-8:25 pm

2 stops17h 10m

$503

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Mon 3/2

6:55 pm-2:40 pm

2 stops16h 45m

San Juan Luis Munoz Marin Intl

Tue 3/3

2:05 am-4:07 pm

2 stops17h 02m

$505

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 4/13

5:10 am-11:40 pm

2 stops15h 30m

San Juan Luis Munoz Marin Intl

Mon 4/20

6:50 am-8:10 pm

2 stops16h 20m

$505

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Sat 4/11

5:00 am-8:38 pm

2 stops13h 38m

San Juan Luis Munoz Marin Intl

Fri 4/17

7:40 am-9:22 pm

2 stops15h 42m

$506

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

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 $188). 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.

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 9h 08m. There are 3374 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 $185 on Delta and JetBlue, 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 $188). 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

Browse thousands of different options on Cheapflights for your next trip

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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$184Average$613FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$185Average$371FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$241Average$382FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$327Average$697FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$359Average$709FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$438Average$704FlexibilityNo cancel feeOn-time63%

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