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Caribbean

$172+ 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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Jun 9 — Jun 161
Tue 6/9
Tue 6/16
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 May 10, 2026.

This American Airlines deal was found by Cheapflights users on 5/6. 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 stop12h 29m
American Airlines
Tue 11/1011:15 am
MBJ
-
PDX
1 stop15h 36m
American Airlines
Deal found 5/6$392
This American Airlines deal was found by Cheapflights users on 5/6. 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 8/2111:59 pm
PDX
-
MBJ
1 stop14h 14m
American Airlines
Fri 8/282:52 pm
MBJ
-
PDX
2 stops21h 59m
American Airlines
Deal found 5/6$397
This United Airlines deal was found by Cheapflights users on 5/9. 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.
Tue 9/294:07 pm
PDX
-
MBJ
2 stops17h 36m
United Airlines
Sun 10/42:40 pm
MBJ
-
PDX
1 stop10h 09m
United Airlines
Deal found 5/9$407
This Delta deal was found by Cheapflights users on 5/8. 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 11/25:45 pm
PDX
-
MBJ
2 stops15h 40m
Delta
Wed 11/116:00 pm
MBJ
-
PDX
2 stops18h 31m
Delta
Deal found 5/8$427
This American Airlines deal was found by Cheapflights users on 5/6. 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.
Sat 9/511:20 pm
PDX
-
MBJ
1 stop11h 57m
American Airlines
Wed 10/712:47 pm
MBJ
-
PDX
1 stop12h 26m
American Airlines
Deal found 5/6$462
This Southwest deal was found by Cheapflights users on 5/8. 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 9/2810:45 pm
PDX
-
SJU
1 stop11h 05m
Southwest
Mon 10/55:00 am
SJU
-
PDX
2 stops12h 40m
Southwest
Deal found 5/8$466
This American Airlines deal was found by Cheapflights users on 5/6. 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.
Sat 9/511:20 pm
PDX
-
MBJ
1 stop11h 57m
American Airlines
Mon 10/510:50 am
MBJ
-
PDX
2 stops27h 53m
American Airlines
Deal found 5/6$467
This United Airlines deal was found by Cheapflights users on 5/6. 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.
Tue 11/106:59 pm
PDX
-
STT
2 stops13h 01m
United Airlines
Tue 11/171:02 pm
STT
-
PDX
1 stop11h 23m
United Airlines
Deal found 5/6$471
This American Airlines deal was found by Cheapflights users on 5/5. 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 8/2410:59 pm
PDX
-
PUJ
1 stop13h 07m
American Airlines
Fri 8/283:11 pm
PUJ
-
PDX
1 stop11h 45m
American Airlines
Deal found 5/5$486
This Southwest deal was found by Cheapflights users on 5/8. 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 8/136:05 am
PDX
-
SJU
2 stops13h 10m
Southwest
Mon 8/176:00 am
SJU
-
PDX
2 stops13h 35m
Southwest
Deal found 5/8$498
This American Airlines deal was found by Cheapflights users on 5/5. 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 5/1510:28 pm
PDX
-
MBJ
1 stop15h 09m
American Airlines
Fri 5/295:17 pm
MBJ
-
PDX
2 stops18h 47m
American Airlines
Deal found 5/5$499
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 9/256:22 pm
PDX
-
SJU
1 stop17h 53m
Multiple Airlines
Fri 10/29:05 pm
SJU
-
PDX
2 stops22h 30m
Multiple Airlines
Deal found 5/8$510

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 May 10, 2026.

Round-trip from

$392
(American Airlines)

One-way from

$172
(American Airlines)

Popular in

December

Cheapest in

October

Average price

$534
From Oregon to Caribbean
Search Deals
One-way flight from Oregon to Caribbean
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($64 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 10, 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

Fri 8/21

11:20 pm-1:34 pm

2 stops12h 14m

Montego Bay Sangster Intl

Fri 8/28

5:13 pm-11:39 am

2 stops20h 26m

$397

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Mon 11/2

7:14 pm-12:25 pm

2 stops14h 11m

Montego Bay Sangster Intl

Tue 11/10

6:00 pm-9:31 am

2 stops18h 31m

$427

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Mon 11/2

3:50 pm-12:25 pm

2 stops17h 35m

Montego Bay Sangster Intl

Wed 11/11

6:00 pm-9:31 am

2 stops18h 31m

$427

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Tue 9/29

6:45 pm-11:43 am

2 stops14h 58m

Montego Bay Sangster Intl

Sun 10/4

2:40 pm-9:30 am

2 stops20h 50m

$458

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Mon 9/28

7:15 pm-12:40 pm

2 stops14h 25m

Punta Cana

Fri 10/9

4:40 pm-9:54 am

1 stop20h 14m

$486

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 6/2

10:52 pm-12:04 pm

1 stop10h 12m

San Juan Luis Munoz Marin Intl

Mon 6/8

1:00 am-9:25 am

1 stop11h 25m

$530

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 7/9

11:40 pm-2:44 pm

1 stop12h 04m

San Juan Luis Munoz Marin Intl

Mon 7/13

1:00 am-9:25 am

1 stop11h 25m

$530

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Mon 9/21

6:57 pm-11:43 am

2 stops14h 46m

Montego Bay Sangster Intl

Wed 9/23

12:52 pm-9:30 am

2 stops22h 38m

$532
Quickest round-trip

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Sat 9/26

5:00 am-5:38 pm

1 stop10h 38m

San Juan Luis Munoz Marin Intl

Sat 10/10

2:00 pm-9:31 pm

1 stop9h 31m

$548

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 7/28

10:57 pm-2:50 pm

2 stops12h 53m

San Juan Luis Munoz Marin Intl

Mon 8/3

7:00 am-11:30 pm

1 stop19h 30m

$551

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/8

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

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 46 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.

What is the cheapest month to book a flight from Oregon to Caribbean?

Currently, May is the cheapest month in which you can book a flight from Oregon to Caribbean (average of $179). Flying from Oregon to Caribbean in February is currently the most expensive (average of $279). 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 12h 14m. There are 3155 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 $185 and $190 on JetBlue and Southwest, 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, May is the cheapest month in which you can book a flight from Oregon to Caribbean (average of $179). Flying from Oregon to Caribbean in February is currently the most expensive (average of $279). 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 May 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$190Average$660FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$224Average$698FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$261Average$484FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$396Average$715FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$408Average$656FlexibilityNo cancel feeOn-time63%

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