Oregon

$144+ Cheap flights from Caribbean to Oregon

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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
Mar 11 — Mar 181
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Caribbean to Oregon with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Caribbean to Oregon

Cheapest flights from Caribbean to Oregon
Explore the most affordable flight options available from Caribbean to Oregon. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 9, 2026.

This Southwest deal was found by Cheapflights users on 2/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/125:05 am
SJU
-
PDX
2 stops18h 55m
Southwest
Sat 5/167:40 pm
PDX
-
SJU
2 stops10h 25m
Southwest
Deal found 2/6$408
This Delta deal was found by Cheapflights users on 2/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/307:30 am
SJU
-
PDX
2 stops15h 35m
Delta
Sat 5/307:00 am
PDX
-
SJU
1 stop10h 06m
Delta
Deal found 2/6$440
This American Airlines deal was found by Cheapflights users on 2/6. 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.
Tue 9/83:00 pm
SJU
-
PDX
1 stop11h 22m
American Airlines
Wed 9/235:56 am
PDX
-
SJU
2 stops15h 03m
American Airlines
Deal found 2/6$449
This American Airlines deal was found by Cheapflights users on 2/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1810:32 am
SJU
-
PDX
2 stops13h 42m
American Airlines
Tue 8/255:38 am
PDX
-
SJU
2 stops15h 02m
American Airlines
Deal found 2/9$478
This Southwest deal was found by Cheapflights users on 2/8. 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 4/98:40 pm
SJU
-
BOI
2 stops18h 00m
Southwest
Wed 4/156:00 am
BOI
-
SJU
2 stops13h 05m
Southwest
Deal found 2/8$481
This American Airlines deal was found by Cheapflights users on 2/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1512:39 am
SJU
-
PDX
1 stop20h 26m
American Airlines
Mon 7/2010:30 pm
PDX
-
SJU
1 stop12h 05m
American Airlines
Deal found 2/8$487
This American Airlines deal was found by Cheapflights users on 2/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1111:59 pm
SJU
-
PDX
1 stop15h 59m
American Airlines
Fri 5/1511:47 pm
PDX
-
SJU
1 stop11h 32m
American Airlines
Deal found 2/8$493
This American Airlines deal was found by Cheapflights users on 2/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/811:59 pm
SJU
-
BOI
1 stop15h 04m
American Airlines
Wed 4/151:51 pm
BOI
-
SJU
1 stop12h 41m
American Airlines
Deal found 2/8$499
This Delta deal was found by Cheapflights users on 2/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/291:25 pm
SJU
-
PDX
1 stop11h 51m
Delta
Sat 5/305:17 am
PDX
-
SJU
2 stops15h 26m
Delta
Deal found 2/6$503
This American Airlines deal was found by Cheapflights users on 2/6. 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.
Tue 2/247:33 am
SJU
-
PDX
2 stops13h 40m
American Airlines
Sat 2/2811:35 pm
PDX
-
SJU
2 stops12h 45m
American Airlines
Deal found 2/6$513
This Southwest deal was found by Cheapflights users on 2/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/15:55 am
SJU
-
PDX
2 stops13h 55m
Southwest
Wed 4/86:30 am
PDX
-
SJU
2 stops13h 10m
Southwest
Deal found 2/6$516
This Delta deal was found by Cheapflights users on 2/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:05 am
SDQ
-
PDX
1 stop19h 11m
Delta
Fri 5/111:06 pm
PDX
-
SDQ
2 stops16h 28m
Delta
Deal found 2/6$517

Find flight deals from Caribbean to Oregon

Keep the following information in mind while searching for Caribbean to Oregon flight deals. Data was last updated February 9, 2026.

Round-trip from

$408
(Southwest)

One-way from

$144
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$545
From Caribbean to Oregon
One-way flight from Caribbean to Oregon
Highest demand for flights based on searches. 6% potential increase in price ($35 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Average for round-trip flights in February 2026

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean to Oregon 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 9, 2026.
Use the filters below to find and compare flights from Caribbean to Oregon that are best for you.

Fly from

Caribbean

Fly to

Oregon

Route

Depart

Return

Price

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 4/30

2:03 pm-9:56 pm

1 stop10h 53m

Portland

Sun 5/31

8:06 pm-4:23 pm

2 stops17h 17m

$440

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Tue 4/21

6:45 am-10:49 pm

1 stop19h 04m

Portland

Sat 4/25

11:40 pm-2:42 pm

1 stop12h 02m

$440

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 4/30

1:25 pm-10:16 pm

1 stop11h 51m

Portland

Sat 5/30

7:00 am-11:43 pm

1 stop13h 43m

$440

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 4/30

1:31 pm-11:57 pm

2 stops13h 26m

Portland

Tue 5/5

11:47 pm-2:52 pm

2 stops12h 05m

$440

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Fri 4/3

7:11 am-12:22 am

1 stop20h 11m

Portland

Mon 4/6

11:30 pm-2:20 pm

1 stop11h 50m

$440

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 4/30

7:30 am-8:05 pm

2 stops15h 35m

Portland

Fri 5/29

5:51 pm-1:18 pm

2 stops16h 27m

$440

San JuanBoise

SJU - BOI

SJUBOI

San Juan Luis Munoz Marin Intl

Thu 4/9

8:40 pm-12:40 pm

2 stops18h 00m

Boise Air Term. Gowen Fld

Wed 4/15

6:00 am-9:05 pm

2 stops13h 05m

$481

San JuanBoise

SJU - BOI

SJUBOI

San Juan Luis Munoz Marin Intl

Wed 4/8

11:59 pm-1:03 pm

1 stop15h 04m

Boise Air Term. Gowen Fld

Wed 4/15

1:51 pm-4:32 am

1 stop12h 41m

$499

Santo DomingoPortland

SDQ - PDX

SDQPDX

Santo Domingo Las Americas

Wed 5/6

7:59 pm-11:46 am

1 stop18h 47m

Portland

Wed 5/13

8:19 pm-6:18 pm

2 stops18h 59m

$517

Santo DomingoPortland

SDQ - PDX

SDQPDX

Santo Domingo Las Americas

Tue 4/28

6:05 am-9:32 pm

2 stops18h 27m

Portland

Fri 5/1

11:15 pm-6:34 pm

2 stops16h 19m

$517

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/7

Showing 1-10 of 56 results
1
2
3
...
6

Best time to book a flight from Caribbean to Oregon

Have a flexible travel schedule? Discover the best time to fly to Oregon from Caribbean 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 Caribbean to Oregon

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

Currently, July is the cheapest month in which you can book a flight from Caribbean to Oregon (average of $237). Flying from Caribbean to Oregon in October is currently the most expensive (average of $481). 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.

Reviews of airlines servicing Oregon

Get insights into the airlines that provide service to Oregon. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Oregon. Reviews last updated February 9, 2026.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Caribbean to Oregon to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Crew

8.6

Entertainment

7.5

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Crew

8.6

Entertainment

7.5

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Crew

8.6

Entertainment

7.5

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Crew

8.6

Entertainment

7.5

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Crew

8.6

Entertainment

7.5

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Caribbean to Oregon. 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 Caribbean to Oregon?

    Delta, American Airlines, and Southwest can get you from Caribbean to Oregon in just under 11h 51m. Your travel time can differ by up to 7h 13m. The distance between Caribbean and Oregon is about 3710 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 Caribbean to Oregon one-way?

    The cheapest airlines for a one-way flight from Caribbean to Oregon are JetBlue ($180), United Airlines ($184), and Delta ($184).

  • Can I find deals for flights from Caribbean to Oregon that include hotel bookings?

    Yes. In addition to deals on Caribbean to Oregon flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Caribbean to Oregon?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Caribbean to Oregon.

  • Can I find deals for business class flights from Caribbean to Oregon?

    Yes. Cheapflights offers flight deals from Caribbean to Oregon 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 Caribbean to Oregon?

    Currently, July is the cheapest month in which you can book a flight from Caribbean to Oregon (average of $237). Flying from Caribbean to Oregon in October is currently the most expensive (average of $481). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Caribbean to Oregon

See prices for flight routes from nearby airports that may be better suited for you.

Top 4 airlines flying from Caribbean to Oregon

Discover the top 4 airlines that operate flights from Caribbean to Oregon. 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 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$190Average$512FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$379Average$550FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$406Average$575FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$466Average$565FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.