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$144+ Cheap flights from Portland (PDX) 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 1/4. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Portland to Caribbean

Cheapest flights from Portland to Caribbean
Explore the most affordable flight options available from Portland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This American Airlines deal was found by Cheapflights users on 12/11. 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 12/1311:59 pmPDX - MBJ
2 stops11h 13mAmerican Airlines
Fri 12/194:11 pmMBJ - PDX
1 stop11h 48mAmerican Airlines
Deal found 12/11$545
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/1410:15 pmPDX - MBJ
1 stop12h 11mAmerican Airlines
Fri 12/1911:07 amMBJ - PDX
1 stop16h 52mAmerican Airlines
Deal found 12/11$553
This American Airlines deal was found by Cheapflights users on 12/10. 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.
Wed 12/1010:45 pmPDX - MBJ
1 stop12h 27mAmerican Airlines
Wed 12/172:02 pmMBJ - PDX
1 stop12h 50mAmerican Airlines
Deal found 12/10$583
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/1310:15 pmPDX - MBJ
1 stop8h 57mAmerican Airlines
Sun 12/211:22 pmMBJ - PDX
1 stop10h 57mAmerican Airlines
Deal found 12/11$588
This eDestinos deal was found by Cheapflights users on 12/10. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/198:45 pmPDX - SJU
3 stops48h 39mMultiple Airlines
Fri 1/97:10 amSJU - PDX
3 stops43h 36mMultiple Airlines
Deal found 12/10$593
This Delta deal was found by Cheapflights users on 12/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/135:30 pmPDX - MBJ
2 stops16h 34mDelta
Sun 12/218:00 amMBJ - PDX
2 stops16h 56mDelta
Deal found 12/10$618
This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1011:19 pmPDX - NAS
1 stop11h 29mUnited Airlines
Fri 12/122:35 pmNAS - PDX
1 stop11h 22mUnited Airlines
Deal found 12/10$625
This Delta deal was found by Cheapflights users on 12/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1011:20 pmPDX - MBJ
2 stops11h 53mDelta
Wed 12/172:29 pmMBJ - PDX
2 stops12h 35mDelta
Deal found 12/10$645
This American Airlines deal was found by Cheapflights users on 12/10. 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.
Sat 12/1310:15 pmPDX - SJU
1 stop12h 00mAmerican Airlines
Sat 12/2010:25 amSJU - PDX
1 stop18h 34mAmerican Airlines
Deal found 12/10$655
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/1310:15 pmPDX - NAS
1 stop12h 44mAmerican Airlines
Tue 12/236:45 pmNAS - PDX
1 stop9h 14mAmerican Airlines
Deal found 12/11$705
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/123:15 pmPDX - SJU
2 stops14h 54mAmerican Airlines
Fri 12/194:38 pmSJU - PDX
2 stops13h 00mAmerican Airlines
Deal found 12/11$715
This Delta deal was found by Cheapflights users on 12/11. 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.
Sat 12/135:15 pmPDX - NAS
2 stops15h 26mDelta
Tue 12/238:10 amNAS - PDX
2 stops16h 49mDelta
Deal found 12/11$719

Find flight deals from Portland to Caribbean

Keep the following information in mind while searching for Portland to Caribbean flight deals. Data was last updated December 12, 2025.

Round-trip from

$369
(Southwest)

One-way from

$144
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$769
From Portland to Caribbean
Search Deals
One-way flight from Portland to Caribbean
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($68 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland 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 December 12, 2025.
Use the filters below to find and compare flights from Portland to Caribbean that are best for you.

Fly from

Portland

Fly to

Caribbean

Route

Depart

Return

Price

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 2/2

7:00 am-9:00 pm

1 stop10h 00m

San Juan Luis Munoz Marin Intl

Thu 2/5

2:15 pm-9:49 pm

1 stop11h 34m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 1/13

7:00 am-9:26 pm

1 stop10h 26m

San Juan Luis Munoz Marin Intl

Wed 2/4

3:46 pm-10:53 pm

1 stop11h 07m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 2/1

1:24 pm-6:11 am

2 stops12h 47m

San Juan Luis Munoz Marin Intl

Tue 2/10

3:46 pm-10:53 pm

1 stop11h 07m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 1/24

9:45 pm-1:06 pm

1 stop11h 21m

San Juan Luis Munoz Marin Intl

Tue 2/3

2:15 pm-10:15 pm

1 stop12h 00m

$429

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 1/25

6:50 am-11:45 pm

1 stop12h 55m

San Juan Luis Munoz Marin Intl

Fri 2/6

3:20 pm-12:17 am

2 stops12h 57m

$429

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 1/23

9:45 pm-1:05 pm

1 stop11h 20m

San Juan Luis Munoz Marin Intl

Tue 2/3

2:15 pm-10:15 pm

1 stop12h 00m

$429

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 1/23

9:45 pm-1:05 pm

1 stop11h 20m

San Juan Luis Munoz Marin Intl

Fri 2/6

7:30 am-8:59 pm

2 stops17h 29m

$429

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 1/9

11:05 pm-2:40 pm

1 stop11h 35m

San Juan Luis Munoz Marin Intl

Wed 1/14

7:45 am-6:56 pm

2 stops15h 11m

$449

PortlandNassau

PDX - NAS

PDXNAS

Portland

Mon 2/23

4:15 pm-1:00 pm

2 stops17h 45m

Nassau Intl

Thu 2/26

1:55 pm-12:05 am

2 stops13h 10m

$485

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 1/24

5:30 am-11:57 pm

2 stops14h 27m

San Juan Luis Munoz Marin Intl

Thu 2/5

7:30 am-8:59 pm

2 stops17h 29m

$490

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 60 results
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Best time to book a flight from Portland to Caribbean

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

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

Currently, August is the cheapest month in which you can book a flight from Portland to Caribbean (average of $186). Flying from Portland to Caribbean in November is currently the most expensive (average of $399). 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 PDX to CB?

Find hourly flight availability from Portland to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 12, 2025.

One of the essential ways to save on airfare from Portland to Caribbean is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 15% on airfare.

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

Use this chart to determine the cheapest time to fly round-trip from Portland to Caribbean. Price data was last updated on December 16, 2024.

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

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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 Caribbean. Reviews last updated December 12, 2025.
Read through reviews of airlines operating flights from Portland to Caribbean, 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
7.9
Good
4,253 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

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
7.9
Good
4,253 reviews
Southwest
7.9
Good
4,253 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

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
8,008 reviews
Southwest
7.9
Good
4,253 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

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
9,095 reviews
Southwest
7.9
Good
4,253 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

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
11,050 reviews
Southwest
7.9
Good
4,253 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

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
Spirit Airlines
6.3
Okay
8,179 reviews
Southwest
7.9
Good
4,253 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

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 Portland to Caribbean. 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 from for flights from Portland to Caribbean?

    For a flight from Portland to Caribbean, you will be flying from Portland. Portland (PDX) is just 6.0 mi from the center of the city.

  • How long is the flight from Portland to Caribbean?

    Airlines like United Airlines, Delta, and Southwest fly from Portland to Caribbean in about 10h. The time it takes to get you to your destination can typically vary by up to 7h 45m. Portland and Caribbean are separated by a distance of 3710 mi. This flight may include one or multiple stops.

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

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $143. Users have also found prices from $150 and $174 on Delta and United Airlines, respectively.

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

    The most popular flight routes from Portland to Caribbean are Portland - San Juan Luis Munoz Marin Intl, Portland - Saint Thomas Island Cyril E King and Portland - Punta Cana.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Portland to Caribbean (average of $186). Flying from Portland to Caribbean in November is currently the most expensive (average of $399). 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

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Top 6 airlines flying from Portland to Caribbean

Discover the top 6 airlines that operate flights from Portland 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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$540FlexibilityNo cancel feeOn-time62%
DeltaCheapest$190Average$723FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$243Average$330FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$347Average$705FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$399Average$687FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$444Average$725FlexibilityNo cancel feeOn-time63%

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