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$161+ Cheap flights from Caribbean 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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
ene. 22 — ene. 291
jue. 1/22
jue. 1/29
1 adult, Economy
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Cheap flight deals from Caribbean to Portland

Cheapest flights from Caribbean to Portland
Explore the most affordable flight options available from Caribbean to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on diciembre 23, 2025.

This American Airlines deal was found by Cheapflights users on 12/21. 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.
jue. 12/251:30 amSJU - PDX
1 stop13h 30mAmerican Airlines
sáb. 1/1011:01 pmPDX - SJU
1 stop14h 00mAmerican Airlines
Deal found 12/21$655
This Delta deal was found by Cheapflights users on 12/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/242:45 pmSJU - PDX
1 stop12h 36mDelta
vie. 1/27:30 pmPDX - SJU
2 stops15h 59mDelta
Deal found 12/22$695
This American Airlines deal was found by Cheapflights users on 12/21. 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.
lun. 12/2212:47 pmSJU - PDX
2 stops14h 19mAmerican Airlines
mar. 1/610:15 pmPDX - SJU
1 stop12h 44mAmerican Airlines
Deal found 12/21$706
This United Airlines deal was found by Cheapflights users on 12/21. 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.
mié. 12/2410:15 amSJU - PDX
2 stops14h 52mUnited Airlines
vie. 1/22:45 pmPDX - SJU
2 stops11h 26mUnited Airlines
Deal found 12/21$745
This United Airlines deal was found by Cheapflights users on 12/21. 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.
lun. 12/2210:15 amSJU - PDX
2 stops16h 44mUnited Airlines
mar. 1/67:00 amPDX - SJU
2 stops13h 36mUnited Airlines
Deal found 12/21$760

Find flight deals from Caribbean to Portland

Keep the following information in mind while searching for Caribbean to Portland flight deals. Data was last updated diciembre 23, 2025.

Round-trip from

$419
(Delta)

One-way from

$161
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$521
From Caribbean to Portland
Search Deals
One-way flight from Caribbean to Portland
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($55 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean 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 diciembre 23, 2025.
Use the filters below to find and compare flights from Caribbean to Portland that are best for you.

Fly from

Caribbean

Fly to

Portland

Route

Depart

Return

Price

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

jue. 1/22

3:55 pm-10:15 pm

1 stop10h 20m

Portland

mar. 1/27

6:50 am-8:58 pm

1 stop10h 08m

$419

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

jue. 1/22

3:46 pm-10:53 pm

1 stop11h 07m

Portland

mar. 1/27

7:00 am-9:00 pm

1 stop10h 00m

$419

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

mar. 2/10

6:00 am-6:51 pm

2 stops16h 51m

Portland

sáb. 2/14

11:59 pm-3:12 pm

1 stop11h 13m

$419

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

jue. 1/22

2:15 pm-10:15 pm

1 stop12h 00m

Portland

lun. 1/26

5:15 pm-1:06 pm

2 stops15h 51m

$419

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

mié. 1/14

8:10 am-6:56 pm

2 stops14h 46m

Portland

dom. 1/18

7:00 am-9:26 pm

1 stop10h 26m

$419

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

jue. 1/15

3:20 pm-12:17 am

2 stops12h 57m

Portland

dom. 1/18

6:50 am-8:58 pm

1 stop10h 08m

$419

AguadillaPortland

BQN - PDX

BQNPDX

Aguadilla Borinquen

mié. 2/18

1:09 am-2:48 pm

2 stops17h 39m

Portland

lun. 2/23

3:50 pm-11:57 pm

3 stops28h 07m

$541

AguadillaPortland

BQN - PDX

BQNPDX

Aguadilla Borinquen

dom. 2/1

1:09 am-11:57 am

2 stops14h 48m

Portland

lun. 2/9

7:00 am-11:57 pm

2 stops12h 57m

$563

Santo DomingoPortland

SDQ - PDX

SDQPDX

Santo Domingo Las Americas

jue. 1/29

7:31 am-8:25 pm

1 stop16h 54m

Portland

vie. 2/6

1:39 pm-1:22 pm

2 stops19h 43m

$578

Santiago de los CaballerosPortland

STI - PDX

STIPDX

Santiago de los Caballeros

jue. 1/22

6:00 am-6:56 pm

2 stops16h 56m

Portland

lun. 1/26

1:24 pm-2:53 pm

3 stops21h 29m

$589

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/20

Showing 1-10 of 44 results
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Best time to book a flight from Caribbean to Portland

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

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

Currently, September is the cheapest month in which you can book a flight from Caribbean to Portland (average of $228). Flying from Caribbean 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.

What is the cheapest time of day to fly from CB to PDX?

Find hourly flight availability from Caribbean to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated diciembre 23, 2025.

It’s optimal to fly from Caribbean to Portland in the evening. By choosing this option you can save up to 28% on the cost of your flight, compared to a flight at noon.

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 diciembre 23, 2025.
Read through reviews of airlines operating flights from Caribbean to Portland, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,253 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

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
Southwest
8.0
Very good
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

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
Delta
7.9
Good
8,014 reviews
Southwest
8.0
Very good
4,253 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

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
United Airlines
7.4
Good
9,105 reviews
Southwest
8.0
Very good
4,253 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

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
American Airlines
7.2
Good
11,054 reviews
Southwest
8.0
Very good
4,253 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

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 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?

    Portland (PDX) is the airport you will fly into if you book a flight from Caribbean 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 to Portland?

    Departing from Caribbean to Portland will take you 10h 20m. The distance between Caribbean and Portland is about 3710 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Caribbean to Portland one-way?

    One-way options have recently been found by users for as low as $180 on American Airlines. Other airlines that offer cheap prices include JetBlue from $180 and United Airlines from $184 one-way.

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

    When deciding which route to take from Caribbean to Portland consider San Juan Luis Munoz Marin Intl - Portland, Montego Bay Sangster Intl - Portland or Santo Domingo Las Americas - Portland as they are the most popular.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Caribbean 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 to Portland?

    Currently, September is the cheapest month in which you can book a flight from Caribbean to Portland (average of $228). Flying from Caribbean 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
Beaverton
McMinnville
Hillsboro
Troutdale
Cannon Beach
Long Beach
Tigard
The Dalles
Depoe Bay
Stevenson
Wilsonville
Tillamook
Pacific City
Gresham

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Top 4 airlines flying from Caribbean to Portland

Discover the top 4 airlines that operate flights from Caribbean 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 diciembre 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$242Average$512FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$369Average$524FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$406Average$570FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$466Average$565FlexibilityNo cancel feeOn-time63%

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