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Caribbean

$176+ 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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Dec 19 — Dec 261
Fri 12/19
Fri 12/26
1 adult, Economy
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Cheap flight deals from Portland to Caribbean

Keep the following information in mind while searching for Portland to Caribbean flight deals. Data was last updated November 19, 2025.

Round-trip from

$394
(Southwest)

One-way from

$176
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$619
From Portland to Caribbean
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One-way flight from Portland to Caribbean
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Highest demand for flights based on searches. 9% potential increase in price ($63 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($18 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 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 November 19, 2025.

This Southwest deal was found by Cheapflights users on 11/18. 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 12/108:00 amPDX - SJU
2 stops12h 35mSouthwest
Thu 12/186:40 amSJU - PDX
2 stops12h 25mSouthwest
Deal found 11/18$447
This United Airlines deal was found by Cheapflights users on 11/18. 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 12/1011:59 pmPDX - SJU
1 stop11h 41mUnited Airlines
Thu 12/182:25 pmSJU - PDX
1 stop12h 34mUnited Airlines
Deal found 11/18$471
This American Airlines deal was found by Cheapflights users on 11/17. 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
Sun 12/211:30 amSJU - PDX
1 stop13h 30mAmerican Airlines
Deal found 11/17$473
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/125:32 pmPDX - SJU
2 stops49h 53mMultiple Airlines
Sun 12/213:14 pmSJU - PDX
1 stop30h 00mMultiple Airlines
Deal found 11/18$475
This Kiwi.com deal was found by Cheapflights users on 11/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/117:04 amPDX - PUJ
1 stop26h 43mMultiple Airlines
Mon 12/156:08 pmPUJ - PDX
2 stops23h 42mMultiple Airlines
Deal found 11/16$481
This American Airlines deal was found by Cheapflights users on 11/17. 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 11/2411:59 pmPDX - SJU
2 stops12h 07mAmerican Airlines
Mon 12/224:38 pmSJU - PDX
1 stop12h 21mAmerican Airlines
Deal found 11/17$482
This American Airlines deal was found by Cheapflights users on 11/18. 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 12/710:45 pmPDX - SJU
1 stop10h 45mAmerican Airlines
Mon 12/155:10 pmSJU - PDX
1 stop10h 42mAmerican Airlines
Deal found 11/18$483
This American Airlines deal was found by Cheapflights users on 11/19. 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 12/1510:45 pmPDX - SJU
1 stop13h 23mAmerican Airlines
Mon 1/197:07 amSJU - PDX
1 stop20h 25mAmerican Airlines
Deal found 11/19$492
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/139:48 amPDX - SJU
2 stops33h 37mMultiple Airlines
Mon 12/225:02 pmSJU - PDX
1 stop28h 12mMultiple Airlines
Deal found 11/17$493
This American Airlines deal was found by Cheapflights users on 11/19. 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 12/1310:45 pmPDX - SJU
1 stop13h 23mAmerican Airlines
Tue 12/234:38 pmSJU - PDX
1 stop12h 21mAmerican Airlines
Deal found 11/19$502
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/177:29 amPDX - MBJ
1 stop28h 00mMultiple Airlines
Wed 12/2410:24 amMBJ - PDX
1 stop13h 26mMultiple Airlines
Deal found 11/19$510
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:16 amPDX - MBJ
1 stop28h 13mMultiple Airlines
Wed 1/73:05 pmMBJ - PDX
2 stops31h 07mMultiple Airlines
Deal found 11/18$522

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 November 19, 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 1/12

9:45 pm-1:05 pm

1 stop11h 20m

San Juan Luis Munoz Marin Intl

Thu 1/15

2:15 pm-10:15 pm

1 stop12h 00m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 1/19

6:00 am-11:45 pm

2 stops13h 45m

San Juan Luis Munoz Marin Intl

Wed 1/28

7:00 am-5:35 pm

2 stops14h 35m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 1/30

6:45 am-12:35 am

2 stops13h 50m

San Juan Luis Munoz Marin Intl

Sat 2/7

6:00 am-4:40 pm

2 stops14h 40m

$444

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Thu 12/11

7:04 am-1:47 pm

1 stop26h 43m

Punta Cana

Mon 12/15

6:08 pm-1:50 pm

2 stops23h 42m

$481

PortlandOranjestad

PDX - AUA

PDXAUA

Portland

Wed 4/15

1:45 pm-12:14 pm

2 stops19h 29m

Oranjestad Reina Beatrix

Tue 4/21

1:55 pm-9:25 am

2 stops22h 30m

$500

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 3/3

5:05 am-9:26 pm

2 stops12h 21m

San Juan Luis Munoz Marin Intl

Tue 3/3

2:05 am-2:48 pm

2 stops16h 43m

$504

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 1/31

7:00 am-9:00 pm

1 stop10h 00m

San Juan Luis Munoz Marin Intl

Fri 2/6

2:05 am-2:46 pm

2 stops16h 41m

$509

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 1/19

3:50 pm-12:55 pm

2 stops17h 05m

San Juan Luis Munoz Marin Intl

Tue 1/27

2:05 am-2:48 pm

2 stops16h 43m

$509

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Wed 12/17

7:29 am-2:29 pm

1 stop28h 00m

Montego Bay Sangster Intl

Wed 12/24

10:24 am-8:50 pm

1 stop13h 26m

$510

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 1/12

6:30 am-11:10 pm

2 stops12h 40m

San Juan Luis Munoz Marin Intl

Sun 1/18

5:40 am-3:40 pm

2 stops14h 00m

$520

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

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 December is currently the most expensive (average of $412). 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 November 19, 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 November 19, 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
8.0
Very good
4,249 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

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
4,249 reviews
Southwest
8.0
Very good
4,249 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

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
8,004 reviews
Southwest
8.0
Very good
4,249 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

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
9,024 reviews
Southwest
8.0
Very good
4,249 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

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
11,046 reviews
Southwest
8.0
Very good
4,249 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

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
Spirit Airlines
6.3
Okay
8,154 reviews
Southwest
8.0
Very good
4,249 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

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 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 Delta, Southwest, and United Airlines fly from Portland to Caribbean in about 11h 20m. The time it takes to get you to your destination can typically vary by up to 2h 30m. 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 Delta. According to our data, you can fly for as low as $210. Users have also found prices from $210 and $232 on American Airlines and Air Canada, 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 - Montego Bay Sangster Intl.

  • 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 December is currently the most expensive (average of $412). 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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Alternative routes for Portland to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Portland to Caribbean

Discover the top 7 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 November 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$540FlexibilityNo cancel feeOn-time62%
DeltaCheapest$190Average$688FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$248Average$415FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$343Average$707FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$400Average$692FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$431Average$587FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$444Average$726FlexibilityNo cancel feeOn-time63%

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