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$209+ 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
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheap flight deals from Caribbean to Portland

Keep the following information in mind while searching for Caribbean to Portland flight deals. Data was last updated November 3, 2025.

Round-trip from

$397
(Southwest)

One-way from

$209
(Kiwi.com)

Popular in

November

Cheapest in

February

Average price

$685
From Caribbean to Portland
Search Deals
One-way flight from Caribbean to Portland
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($85 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find 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 November 3, 2025.

This Southwest deal was found by Cheapflights users on 11/2. 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 12/22:05 pmSJU - PDX
2 stops12h 30mSouthwest
Tue 12/96:55 pmPDX - SJU
2 stops11h 30mSouthwest
Deal found 11/2$397
This United Airlines deal was found by Cheapflights users on 11/3. 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 12/82:10 pmSJU - PDX
1 stop11h 35mUnited Airlines
Thu 12/115:00 amPDX - SJU
2 stops13h 22mUnited Airlines
Deal found 11/3$419
This American Airlines deal was found by Cheapflights users on 11/2. 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 12/2210:25 amSJU - PDX
1 stop18h 34mAmerican Airlines
Tue 1/611:01 pmPDX - SJU
1 stop14h 00mAmerican Airlines
Deal found 11/2$427
This American Airlines deal was found by Cheapflights users on 11/2. 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 11/183:56 pmSJU - PDX
1 stop11h 30mAmerican Airlines
Thu 12/410:15 pmPDX - SJU
1 stop19h 54mAmerican Airlines
Deal found 11/2$482
This eDestinos deal was found by Cheapflights users on 11/3. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/233:55 amSJU - PDX
2 stops35h 48mMultiple Airlines
Fri 1/211:20 pmPDX - SJU
1 stop27h 14mMultiple Airlines
Deal found 11/3$492
This eDestinos deal was found by Cheapflights users on 11/3. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:22 pmSJU - PDX
2 stops31h 48mMultiple Airlines
Tue 1/66:14 amPDX - SJU
2 stops29h 59mMultiple Airlines
Deal found 11/3$496
This American Airlines deal was found by Cheapflights users on 11/3. 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 12/2410:25 amSJU - PDX
1 stop18h 34mAmerican Airlines
Fri 1/23:02 pmPDX - SJU
1 stop9h 58mAmerican Airlines
Deal found 11/3$501
This Southwest deal was found by Cheapflights users on 11/3. 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 12/88:55 amSJU - PDX
2 stops14h 25mSouthwest
Thu 12/116:15 amPDX - SJU
2 stops11h 50mSouthwest
Deal found 11/3$520
This Gotogate deal was found by Cheapflights users on 11/3. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/77:05 pmMBJ - PDX
2 stops41h 10mAir Canada
Fri 11/283:15 pmPDX - MBJ
2 stops18h 55mAir Canada
Deal found 11/3$657
This Delta deal was found by Cheapflights users on 11/3. 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.
Fri 11/72:32 pmMBJ - PDX
1 stop10h 36mDelta
Fri 11/285:26 pmPDX - MBJ
2 stops18h 04mDelta
Deal found 11/3$659
This United Airlines deal was found by Cheapflights users on 11/2. 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.
Wed 12/175:45 pmGCM - PDX
2 stops26h 46mUnited Airlines
Wed 12/2410:52 pmPDX - GCM
1 stop14h 43mUnited Airlines
Deal found 11/2$674
This American Airlines deal was found by Cheapflights users on 11/3. 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 11/712:22 pmMBJ - PDX
1 stop10h 56mAmerican Airlines
Fri 11/281:47 pmPDX - MBJ
1 stop20h 13mAmerican Airlines
Deal found 11/3$680

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 November 3, 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

Tue 12/2

2:05 pm-10:35 pm

2 stops12h 30m

Portland

Tue 12/9

6:55 pm-10:25 am

2 stops11h 30m

$397

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Mon 12/8

2:10 pm-9:45 pm

1 stop11h 35m

Portland

Thu 12/11

5:00 am-10:22 pm

2 stops13h 22m

$419

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 2/26

6:15 am-6:50 pm

2 stops16h 35m

Portland

Mon 3/2

7:00 am-11:58 pm

1 stop12h 58m

$419

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Mon 12/22

10:25 am-12:59 am

1 stop18h 34m

Portland

Tue 1/6

11:01 pm-5:01 pm

1 stop14h 00m

$427

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Tue 11/18

2:47 pm-11:31 pm

1 stop12h 44m

Portland

Thu 12/4

10:15 pm-10:09 pm

1 stop19h 54m

$482

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Wed 2/25

2:05 am-2:48 pm

2 stops16h 43m

Portland

Mon 3/2

3:50 pm-2:40 pm

2 stops18h 50m

$499

AguadillaPortland

BQN - PDX

BQNPDX

Aguadilla Borinquen

Wed 2/25

1:09 am-2:48 pm

2 stops17h 39m

Portland

Mon 3/2

7:00 am-11:57 pm

2 stops12h 57m

$509

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Mon 12/8

8:55 am-7:20 pm

2 stops14h 25m

Portland

Thu 12/11

6:15 am-10:05 pm

2 stops11h 50m

$520

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Fri 11/14

7:45 am-8:38 pm

2 stops16h 53m

Portland

Fri 11/14

11:59 pm-3:40 pm

1 stop11h 41m

$540

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Sat 2/28

8:00 am-10:39 pm

1 stop17h 39m

Portland

Tue 3/3

9:45 pm-3:15 pm

1 stop14h 30m

$543

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 53 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 $488). 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 November 3, 2025.

It’s optimal to fly from Caribbean to Portland in the evening. By choosing this option you can save up to 23% on the cost of your flight, compared to a flight at noon.

What is the cheapest day to fly from Caribbean to Portland?

Use this chart to determine the cheapest time to fly round-trip from Caribbean to Portland. Price data was last updated on December 8, 2024.

Travelers seeking maximum savings on their Caribbean to Portland flight should consider departing on Saturday afternoons when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 November 3, 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
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
8,002 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,997 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,038 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 11h 35m. 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 $209 on Frontier. Other airlines that offer cheap prices include Delta from $313 and American Airlines from $315 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, Santo Domingo Las Americas - Portland or George Town Owen Roberts Intl - 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 $488). 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
Lake Oswego
Beaverton
McMinnville
Hillsboro
Cannon Beach
Long Beach
Longview
Tigard
The Dalles
Depoe Bay
Stevenson
Wilsonville
Pacific City
Gresham
Tillamook
Troutdale

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Caribbean to Portland

See prices for flight routes from nearby airports that may be better suited for you.
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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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$242Average$522FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$349Average$497FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$406Average$573FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$466Average$565FlexibilityNo cancel feeOn-time63%

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