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Caribbean

$162+ 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Apr 18 — Apr 251
Sat 4/18
Sat 4/25
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 March 19, 2026.

This American Airlines deal was found by Cheapflights users on 3/16. 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 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 stop8h 30m
American Airlines
Tue 11/1011:15 am
MBJ
-
PDX
1 stop15h 36m
American Airlines
Deal found 3/16$392
This American Airlines deal was found by Cheapflights users on 3/17. 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 4/2010:23 pm
PDX
-
STT
1 stop13h 27m
American Airlines
Wed 4/222:05 pm
STT
-
PDX
1 stop12h 48m
American Airlines
Deal found 3/17$400
This United Airlines deal was found by Cheapflights users on 3/16. 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.
Mon 4/137:14 pm
PDX
-
STT
2 stops17h 17m
United Airlines
Mon 4/202:10 pm
STT
-
PDX
1 stop11h 24m
United Airlines
Deal found 3/16$420
This American Airlines deal was found by Cheapflights users on 3/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1511:47 pm
PDX
-
STT
2 stops13h 28m
American Airlines
Wed 4/2212:25 pm
STT
-
PDX
2 stops14h 32m
American Airlines
Deal found 3/16$425
This Delta deal was found by Cheapflights users on 3/18. 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 11/25:10 pm
PDX
-
MBJ
2 stops16h 15m
Delta
Wed 11/116:00 pm
MBJ
-
PDX
2 stops18h 31m
Delta
Deal found 3/18$427
This Southwest deal was found by Cheapflights users on 3/15. 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.
Tue 9/226:25 pm
PDX
-
SJU
2 stops13h 35m
Southwest
Wed 9/231:45 pm
SJU
-
PDX
2 stops12h 10m
Southwest
Deal found 3/15$441
This Delta deal was found by Cheapflights users on 3/18. 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 4/1311:35 pm
BOI
-
SJU
1 stop11h 50m
Delta
Fri 4/176:15 am
SJU
-
BOI
2 stops17h 41m
Delta
Deal found 3/18$444
This Southwest deal was found by Cheapflights users on 3/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:30 am
PDX
-
SJU
2 stops13h 10m
Southwest
Tue 5/1211:25 am
SJU
-
PDX
2 stops13h 35m
Southwest
Deal found 3/14$444
This United Airlines deal was found by Cheapflights users on 3/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/307:05 pm
PDX
-
MBJ
2 stops18h 05m
United Airlines
Thu 5/72:40 pm
MBJ
-
PDX
1 stop10h 19m
United Airlines
Deal found 3/15$445
This Southwest deal was found by Cheapflights users on 3/17. 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.
Fri 9/1110:45 pm
PDX
-
SJU
1 stop11h 25m
Southwest
Thu 9/1710:00 am
SJU
-
PDX
2 stops13h 45m
Southwest
Deal found 3/17$446
This United Airlines deal was found by Cheapflights users on 3/16. 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.
Mon 5/410:15 pm
PDX
-
MBJ
1 stop11h 28m
United Airlines
Mon 5/182:40 pm
MBJ
-
PDX
2 stops20h 58m
United Airlines
Deal found 3/16$450
This United Airlines deal was found by Cheapflights users on 3/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3011:59 pm
PDX
-
MBJ
1 stop11h 31m
United Airlines
Mon 5/42:40 pm
MBJ
-
PDX
2 stops23h 55m
United Airlines
Deal found 3/15$455

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 March 19, 2026.

Round-trip from

$397
(American Airlines)

One-way from

$162
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$683
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 ($72 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 19, 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

Sun 4/19

11:47 pm-1:25 pm

2 stops11h 38m

Montego Bay Sangster Intl

Wed 4/22

10:17 am-10:56 pm

2 stops14h 39m

$397
Quickest round-trip

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Tue 4/14

11:15 pm-1:08 pm

1 stop10h 53m

Saint Thomas Island Cyril E King

Tue 4/21

1:22 pm-9:59 pm

1 stop11h 37m

$420

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Mon 4/13

8:40 pm-12:52 pm

2 stops14h 12m

San Juan Luis Munoz Marin Intl

Fri 4/17

6:15 am-9:56 pm

2 stops17h 41m

$444

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Sun 4/19

10:55 pm-3:17 pm

1 stop14h 22m

Montego Bay Sangster Intl

Wed 4/22

2:10 pm-10:02 pm

1 stop9h 52m

$462

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Mon 4/20

8:40 pm-12:52 pm

2 stops14h 12m

San Juan Luis Munoz Marin Intl

Sat 4/25

6:15 am-5:21 pm

2 stops13h 06m

$464

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Mon 4/13

11:35 pm-11:45 am

1 stop10h 10m

San Juan Luis Munoz Marin Intl

Wed 4/22

6:15 am-9:24 pm

2 stops17h 09m

$464

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 7/9

5:55 am-9:30 pm

2 stops12h 35m

San Juan Luis Munoz Marin Intl

Mon 7/13

5:30 am-4:20 pm

1 stop13h 50m

$478

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 8/10

10:45 pm-12:50 pm

1 stop11h 05m

San Juan Luis Munoz Marin Intl

Mon 8/17

5:30 am-3:00 pm

1 stop12h 30m

$478

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 7/30

7:40 pm-10:45 am

2 stops12h 05m

San Juan Luis Munoz Marin Intl

Sat 8/15

8:20 am-8:00 pm

2 stops14h 40m

$490

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Mon 4/20

11:59 pm-3:31 pm

1 stop12h 32m

Saint Thomas Island Cyril E King

Wed 4/22

1:22 pm-9:59 pm

1 stop11h 37m

$510

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/18

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, August is the cheapest month in which you can book a flight from Oregon to Caribbean (average of $185). Flying from Oregon to Caribbean in January is currently the most expensive (average of $405). 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 10h 53m. There are 3764 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 $149 and $150 on United Airlines and Delta, 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 $185). Flying from Oregon to Caribbean in January is currently the most expensive (average of $405). 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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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 March 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$184Average$643FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$185Average$526FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$241Average$415FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$327Average$676FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$399Average$698FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$408Average$674FlexibilityNo cancel feeOn-time63%

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