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Caribbean

$192+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Jul 24 — Jul 311
Fri 7/24
Fri 7/31
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 June 24, 2026.

This American Airlines deal was found by Cheapflights users on 6/23. 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.
Fri 8/2111:34 pm
PDX
-
STT
2 stops13h 18m
American Airlines
Fri 8/283:43 pm
STT
-
PDX
2 stops22h 51m
American Airlines
Deal found 6/23$420
This American Airlines deal was found by Cheapflights users on 6/19. 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 8/1911:34 pm
PDX
-
STT
2 stops13h 18m
American Airlines
Sat 8/294:42 pm
STT
-
PDX
2 stops21h 52m
American Airlines
Deal found 6/19$425
This American Airlines deal was found by Cheapflights users on 6/24. 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 11/210:45 pm
PDX
-
MBJ
1 stop11h 10m
American Airlines
Tue 11/104:05 pm
MBJ
-
PDX
1 stop10h 46m
American Airlines
Deal found 6/24$432
This Delta deal was found by Cheapflights users on 6/24. 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 11/25:05 pm
PDX
-
MBJ
2 stops16h 20m
Delta
Tue 11/106:00 pm
MBJ
-
PDX
2 stops18h 16m
Delta
Deal found 6/24$437
This United Airlines deal was found by Cheapflights users on 6/23. 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 11/95:00 am
PDX
-
SJU
1 stop9h 25m
United Airlines
Tue 11/172:21 pm
SJU
-
PDX
1 stop10h 47m
United Airlines
Deal found 6/23$466
This Southwest deal was found by Cheapflights users on 6/24. 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 8/207:35 pm
PDX
-
STT
2 stops15h 15m
Southwest
Fri 8/282:35 pm
STT
-
PDX
2 stops12h 05m
Southwest
Deal found 6/24$469
This American Airlines deal was found by Cheapflights users on 6/21. 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 8/1211:34 pm
PDX
-
SJU
1 stop20h 41m
American Airlines
Thu 8/2012:55 am
SJU
-
PDX
1 stop13h 39m
American Airlines
Deal found 6/21$471
This American Airlines deal was found by Cheapflights users on 6/24. 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 11/210:45 pm
PDX
-
MBJ
1 stop11h 10m
American Airlines
Wed 11/114:02 pm
MBJ
-
PDX
1 stop9h 57m
American Airlines
Deal found 6/24$473
This American Airlines deal was found by Cheapflights users on 6/20. 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 10/276:33 pm
PDX
-
MBJ
2 stops12h 32m
American Airlines
Tue 11/104:05 pm
MBJ
-
PDX
2 stops21h 53m
American Airlines
Deal found 6/20$478
This Southwest deal was found by Cheapflights users on 6/22. 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 8/177:00 pm
PDX
-
SJU
2 stops13h 00m
Southwest
Mon 8/245:30 am
SJU
-
PDX
1 stop12h 30m
Southwest
Deal found 6/22$481
This United Airlines deal was found by Cheapflights users on 6/23. 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.
Thu 7/2311:40 pm
PDX
-
SJU
1 stop12h 04m
United Airlines
Tue 7/281:00 am
SJU
-
PDX
1 stop11h 25m
United Airlines
Deal found 6/23$487
This United Airlines deal was found by Cheapflights users on 6/21. 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.
Thu 10/1510:33 pm
PDX
-
SJU
1 stop10h 24m
United Airlines
Tue 10/201:25 pm
SJU
-
PDX
1 stop11h 02m
United Airlines
Deal found 6/21$488

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 June 24, 2026.

Round-trip from

$420
(American Airlines)

One-way from

$192
(United Airlines)

Popular in

March

Cheapest in

September

Average price

$676
From Oregon to Caribbean
Search Deals
One-way flight from Oregon to Caribbean
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 24, 2026.
Use the filters below to find and compare flights from Oregon to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Tue 10/27

7:40 pm-11:25 am

2 stops13h 45m

Montego Bay Sangster Intl

Tue 11/10

6:00 pm-9:31 am

2 stops18h 31m

$437

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Mon 11/2

5:05 pm-12:25 pm

2 stops16h 20m

Montego Bay Sangster Intl

Tue 11/10

6:00 pm-9:16 am

2 stops18h 16m

$437

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 11/9

7:35 pm-1:15 pm

2 stops13h 40m

San Juan Luis Munoz Marin Intl

Tue 11/17

2:21 pm-9:08 pm

1 stop10h 47m

$466

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 9/26

5:10 pm-12:13 pm

2 stops16h 03m

San Juan Luis Munoz Marin Intl

Sat 10/31

12:46 pm-11:47 pm

2 stops14h 01m

$466

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 11/18

6:00 am-11:55 pm

2 stops13h 55m

San Juan Luis Munoz Marin Intl

Thu 11/26

1:55 pm-11:51 pm

2 stops13h 56m

$466

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 11/12

5:30 am-11:55 pm

2 stops14h 25m

San Juan Luis Munoz Marin Intl

Tue 11/17

7:15 am-6:17 pm

2 stops15h 02m

$466

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 10/17

10:05 pm-11:56 am

1 stop10h 51m

San Juan Luis Munoz Marin Intl

Thu 10/22

1:06 pm-11:52 pm

2 stops13h 46m

$466

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 7/23

11:40 pm-2:44 pm

1 stop12h 04m

San Juan Luis Munoz Marin Intl

Tue 7/28

1:00 am-9:25 am

1 stop11h 25m

$487

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Thu 8/20

7:35 pm-1:50 pm

2 stops15h 15m

Saint Thomas Island Cyril E King

Fri 8/28

2:35 pm-11:40 pm

2 stops12h 05m

$489

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Wed 10/28

8:10 am-9:40 pm

2 stops11h 30m

San Juan Luis Munoz Marin Intl

Mon 11/2

6:05 am-4:05 pm

2 stops13h 00m

$496

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/19

Showing 1-10 of 60 resultsSorted by cheapest first
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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, March is the cheapest month in which you can book a flight from Oregon to Caribbean (average of $191). Flying from Oregon to Caribbean in May is currently the most expensive (average of $365). 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.

How far ahead should I book a flight from Oregon to Caribbean?

To ensure you get the cheapest price possible for a flight from Oregon to Caribbean, you should look to book at least 19 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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 13h 40m. There are 3710 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 $172. Users have also found prices from $190 and $190 on Southwest 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, March is the cheapest month in which you can book a flight from Oregon to Caribbean (average of $191). Flying from Oregon to Caribbean in May is currently the most expensive (average of $365). 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 5 airlines flying from Oregon to Caribbean

Discover the top 5 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 June 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$190Average$712FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$247Average$715FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$261Average$478FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$392Average$737FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$408Average$601FlexibilityNo cancel feeOn-time63%

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