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$129+ Cheap flights from Caribbean Islands to Portland (PDX)

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 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
Mar 16 — Mar 231
Mon 3/16
Mon 3/23
1 adult, Economy
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Cheap flight deals from Caribbean Islands to Portland

Cheapest flights from Caribbean Islands to Portland
Explore the most affordable flight options available from Caribbean Islands to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 14, 2026.

This Southwest deal was found by Cheapflights users on 2/12. 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 4/2811:25 am
SJU
-
PDX
2 stops14h 45m
Southwest
Tue 5/55:40 am
PDX
-
SJU
2 stops12h 25m
Southwest
Deal found 2/12$386
This Delta deal was found by Cheapflights users on 2/13. 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 4/301:25 pm
SJU
-
PDX
1 stop11h 51m
Delta
Tue 5/57:00 am
PDX
-
SJU
1 stop13h 59m
Delta
Deal found 2/13$450
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Sun 5/105:45 am
SJU
-
PDX
1 stop21h 08m
American Airlines
Sat 5/1611:40 pm
PDX
-
SJU
1 stop20h 22m
American Airlines
Deal found 2/10$461
This United Airlines deal was found by Cheapflights users on 2/12. 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 3/58:05 am
SJU
-
PDX
2 stops15h 09m
United Airlines
Tue 3/1711:10 pm
PDX
-
SJU
1 stop10h 07m
United Airlines
Deal found 2/12$466
This Southwest deal was found by Cheapflights users on 2/12. 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 6/12:00 pm
SJU
-
PDX
2 stops13h 25m
Southwest
Mon 6/159:20 pm
PDX
-
SJU
1 stop12h 20m
Southwest
Deal found 2/12$471
This United Airlines deal was found by Cheapflights users on 2/13. 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 8/133:56 pm
SJU
-
PDX
1 stop10h 56m
United Airlines
Sun 8/1611:30 pm
PDX
-
SJU
1 stop10h 04m
United Airlines
Deal found 2/13$483
This Southwest deal was found by Cheapflights users on 2/10. 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 4/2111:25 am
SJU
-
PDX
2 stops14h 35m
Southwest
Sat 4/258:00 am
PDX
-
SJU
2 stops12h 40m
Southwest
Deal found 2/10$485
This American Airlines deal was found by Cheapflights users on 2/10. 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 4/205:45 am
SJU
-
PDX
1 stop21h 08m
American Airlines
Sat 4/2510:28 pm
PDX
-
SJU
1 stop16h 42m
American Airlines
Deal found 2/10$486
This American Airlines deal was found by Cheapflights users on 2/12. 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 4/2811:43 am
SJU
-
PDX
2 stops14h 06m
American Airlines
Thu 5/2810:59 pm
PDX
-
SJU
2 stops13h 49m
American Airlines
Deal found 2/12$488
This Delta deal was found by Cheapflights users on 2/12. 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 4/287:15 am
SJU
-
PDX
2 stops19h 40m
Delta
Mon 5/411:15 pm
PDX
-
SJU
1 stop10h 37m
Delta
Deal found 2/12$503
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Sun 5/105:45 am
SJU
-
PDX
1 stop21h 08m
American Airlines
Fri 5/1511:47 pm
PDX
-
SJU
2 stops12h 48m
American Airlines
Deal found 2/10$504
This American Airlines deal was found by Cheapflights users on 2/10. 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 9/82:25 pm
SJU
-
PDX
1 stop13h 33m
American Airlines
Wed 9/2310:43 pm
PDX
-
SJU
1 stop13h 02m
American Airlines
Deal found 2/10$511

Find flight deals from Caribbean Islands to Portland

Keep the following information in mind while searching for Caribbean Islands to Portland flight deals. Data was last updated February 14, 2026.

Round-trip from

$386
(Southwest)

One-way from

$129
(Kiwi.com)
From Caribbean Islands to Portland
Search Deals
One-way flight from Caribbean Islands to Portland
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean Islands to Portland 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 14, 2026.
Use the filters below to find and compare flights from Caribbean Islands to Portland that are best for you.

Fly from

Caribbean Islands

Fly to

Portland

Route

Depart

Return

Price

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Fri 4/3

6:33 am-10:02 pm

1 stop18h 29m

Portland

Thu 4/16

10:28 pm-10:53 am

1 stop9h 25m

$450

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 4/30

1:25 pm-10:16 pm

1 stop11h 51m

Portland

Tue 5/5

7:00 am-11:59 pm

1 stop13h 59m

$450

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Fri 3/6

2:25 pm-9:10 pm

1 stop10h 45m

Portland

Mon 3/23

10:54 pm-1:40 pm

1 stop11h 46m

$450

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Sun 5/10

5:45 am-11:53 pm

1 stop21h 08m

Portland

Fri 5/15

11:47 pm-2:19 pm

1 stop11h 32m

$450

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Tue 4/21

6:45 am-10:49 pm

1 stop19h 04m

Portland

Fri 4/24

12:59 am-2:42 pm

1 stop10h 43m

$450

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

11:40 pm-2:52 pm

2 stops12h 12m

$450

Santo DomingoPortland

SDQ - PDX

SDQPDX

Santo Domingo Las Americas

Wed 3/18

10:19 am-11:44 pm

2 stops16h 25m

Portland

Wed 3/25

9:30 pm-2:40 am

1 stop26h 10m

$518

Santo DomingoPortland

SDQ - PDX

SDQPDX

Santo Domingo Las Americas

Tue 4/28

6:05 am-10:16 pm

1 stop19h 11m

Portland

Fri 5/1

7:00 am-12:17 am

1 stop14h 17m

$529

Santo DomingoPortland

SDQ - PDX

SDQPDX

Santo Domingo Las Americas

Fri 4/24

6:05 am-10:16 pm

1 stop19h 11m

Portland

Sun 5/3

6:05 pm-12:31 pm

2 stops15h 26m

$529

AguadillaPortland

BQN - PDX

BQNPDX

Aguadilla Borinquen

Thu 4/30

12:15 am-12:59 am

2 stops27h 44m

Portland

Tue 5/5

5:00 am-11:09 pm

2 stops15h 09m

$601

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/11

Showing 1-10 of 56 results
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Best time to book a flight from Caribbean Islands to Portland

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

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

Currently, July is the cheapest month in which you can book a flight from Caribbean Islands to Portland (average of $237). Flying from Caribbean Islands to Portland 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 Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated February 14, 2026.
Read through reviews of airlines operating flights from Caribbean Islands to Portland, such as American Airlines. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,288 reviews

Food

6.4

Overall

7.2

Boarding

7.5

Crew

8.0

Entertainment

6.9

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,288 reviews
American Airlines
7.2
Good
11,288 reviews

Food

6.4

Overall

7.2

Boarding

7.5

Crew

8.0

Entertainment

6.9

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

Related info for your journey

Find useful and relevant information for your journey from Caribbean Islands to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Portland from Caribbean Islands?

    Portland (PDX) is the airport you will fly into if you book a flight from Caribbean Islands to Portland. It is only a 6.0 mi journey from Portland (PDX) to Portland’s city center.

  • How long is the flight from Caribbean Islands to Portland?

    For as low as $450, American Airlines can have you in Portland from Caribbean Islands in 11h 51m. The distance from Caribbean Islands to Portland 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 Islands to Portland one-way?

    The cheapest airline one-way is JetBlue, with whom users have recently found tickets for as low as $180. However, be on the lookout for offers from United Airlines and Delta, as they are both options that can get you from Caribbean Islands to Portland for a low price.

  • What are the most popular routes from Caribbean Islands to Portland?

    Most travelers choose San Juan Luis Munoz Marin Intl - Portland, Santo Domingo Las Americas - Portland or Kingston Norman Manley - Portland when deciding on the best route from Caribbean Islands to Portland.

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

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

  • How can I find direct flights from Caribbean Islands to Portland?

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

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

    Yes. Cheapflights offers flight deals from Caribbean Islands to Portland 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 Islands to Portland?

    Currently, July is the cheapest month in which you can book a flight from Caribbean Islands to Portland (average of $237). Flying from Caribbean Islands to Portland 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

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
Vancouver
Seaside
Clackamas
Lincoln City
Longview
Lake Oswego
Hillsboro
Troutdale
Cannon Beach
Long Beach
McMinnville
Tigard
The Dalles
Beaverton
Depoe Bay
Stevenson
Wilsonville
Tillamook
Pacific City
Gresham

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Top 4 airlines flying from Caribbean Islands to Portland

Discover the top 4 airlines that operate flights from Caribbean Islands to Portland. 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 14, 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%

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