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Caribbean

$183+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Feb 5 — Feb 121
Thu 2/5
Thu 2/12
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 January 6, 2026.

Round-trip from

$416
(United Airlines)

One-way from

$183
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$552
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. 11% potential increase in price ($76 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 January 2026
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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 January 6, 2026.

This United Airlines deal was found by Cheapflights users on 1/6. 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 5/2810:00 amPDX - SJU
1 stop10h 57mUnited Airlines
Thu 6/47:45 amSJU - PDX
1 stop13h 20mUnited Airlines
Deal found 1/6$416
This Delta deal was found by Cheapflights users on 1/6. 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 4/175:59 pmPDX - SJU
2 stops16h 15mDelta
Tue 4/281:15 pmSJU - PDX
1 stop11h 55mDelta
Deal found 1/6$420
This American Airlines deal was found by Cheapflights users on 1/6. 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 4/16:40 amPDX - SJU
1 stop12h 51mAmerican Airlines
Wed 4/153:07 pmSJU - PDX
1 stop11h 34mAmerican Airlines
Deal found 1/6$427
This American Airlines deal was found by Cheapflights users on 1/5. 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 4/2110:45 pmPDX - SJU
1 stop16h 21mAmerican Airlines
Mon 5/411:59 pmSJU - PDX
1 stop14h 02mAmerican Airlines
Deal found 1/5$432
This Southwest deal was found by Cheapflights users on 1/5. 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 3/36:45 amPDX - SJU
2 stops13h 50mSouthwest
Thu 3/125:30 amSJU - PDX
2 stops11h 55mSouthwest
Deal found 1/5$433
This Southwest deal was found by Cheapflights users on 1/6. 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.
Fri 2/65:35 amPDX - SJU
2 stops15h 05mSouthwest
Wed 2/116:10 amSJU - PDX
2 stops13h 30mSouthwest
Deal found 1/6$448
This American Airlines deal was found by Cheapflights users on 1/6. 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 2/211:01 pmPDX - SJU
1 stop14h 00mAmerican Airlines
Mon 3/27:00 amSJU - PDX
1 stop20h 50mAmerican Airlines
Deal found 1/6$458
This United Airlines deal was found by Cheapflights users on 1/4. 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 5/66:59 pmPDX - SJU
2 stops14h 35mUnited Airlines
Fri 5/157:40 amSJU - PDX
1 stop13h 25mUnited Airlines
Deal found 1/4$462
This United Airlines deal was found by Cheapflights users on 1/5. 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 7/2311:59 pmPDX - SJU
1 stop12h 43mUnited Airlines
Thu 7/301:05 amSJU - PDX
1 stop11h 16mUnited Airlines
Deal found 1/5$472
This Delta deal was found by Cheapflights users on 1/6. 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 3/3112:30 amPDX - SJU
2 stops12h 48mDelta
Wed 4/151:50 pmSJU - PDX
2 stops13h 03mDelta
Deal found 1/6$473
This American Airlines deal was found by Cheapflights users on 1/5. 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 8/117:00 amPDX - SJU
2 stops13h 40mAmerican Airlines
Sat 8/2212:00 pmSJU - PDX
2 stops14h 22mAmerican Airlines
Deal found 1/5$474
This American Airlines deal was found by Cheapflights users on 1/5. 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.
Thu 1/2910:15 pmPDX - STX
1 stop13h 14mAmerican Airlines
Mon 2/28:30 amSTX - PDX
1 stop19h 16mAmerican Airlines
Deal found 1/5$486

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 January 6, 2026.
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

Fri 4/17

5:59 pm-11:58 am

2 stops14h 59m

San Juan Luis Munoz Marin Intl

Thu 4/23

1:50 pm-9:42 pm

1 stop10h 52m

$420

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 2/3

5:00 am-6:25 pm

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Tue 2/10

8:10 am-6:56 pm

2 stops14h 46m

$420

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 2/2

12:40 am-4:50 pm

2 stops12h 10m

San Juan Luis Munoz Marin Intl

Tue 2/10

3:55 pm-10:15 pm

1 stop10h 20m

$420

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 3/4

12:40 am-9:12 pm

2 stops16h 32m

San Juan Luis Munoz Marin Intl

Thu 3/12

1:00 pm-10:09 pm

1 stop12h 09m

$420

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 2/6

5:35 am-12:40 am

2 stops15h 05m

San Juan Luis Munoz Marin Intl

Tue 2/10

6:10 am-3:40 pm

2 stops13h 30m

$448

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 4/20

10:55 pm-1:14 pm

1 stop11h 19m

San Juan Luis Munoz Marin Intl

Thu 4/30

1:50 pm-9:42 pm

1 stop10h 52m

$473

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 1/19

9:45 pm-1:06 pm

1 stop11h 21m

San Juan Luis Munoz Marin Intl

Wed 1/28

7:00 am-8:32 pm

2 stops17h 32m

$483

PortlandChristiansted

PDX - STX

PDXSTX

Portland

Fri 3/6

10:53 pm-5:37 pm

1 stop14h 44m

Christiansted Henry Rohlsen

Fri 3/13

1:50 pm-11:44 pm

1 stop12h 54m

$486

PortlandChristiansted

PDX - STX

PDXSTX

Portland

Thu 1/29

10:15 pm-3:29 pm

1 stop13h 14m

Christiansted Henry Rohlsen

Mon 2/2

8:30 am-11:46 pm

1 stop19h 16m

$486

PortlandChristiansted

PDX - STX

PDXSTX

Portland

Sat 3/14

10:30 pm-1:18 pm

1 stop11h 48m

Christiansted Henry Rohlsen

Thu 3/19

2:24 pm-10:09 pm

1 stop10h 45m

$486

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/5

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.

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 January 6, 2026.
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
4,248 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

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
8,018 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

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
9,132 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

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
11,084 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

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
8,271 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

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 Delta, United Airlines, and American Airlines fly from Portland to Caribbean in about 9h 25m. The time it takes to get you to your destination can typically vary by up to 5h 34m. 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 $182 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 - Nassau 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 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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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 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 January 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$540FlexibilityNo cancel feeOn-time62%
DeltaCheapest$190Average$749FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$243Average$358FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$348Average$714FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$405Average$706FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$445Average$735FlexibilityNo cancel feeOn-time63%

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