Caribbean

$128+ 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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Feb 25 — Mar 41
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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 January 26, 2026.

This Frontier deal was found by Cheapflights users on 1/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/912:27 pm
PDX
-
PUJ
2 stops19h 10m
Frontier
Sat 5/1611:07 am
PUJ
-
PDX
2 stops24h 52m
Frontier
Deal found 1/26$436
This American Airlines deal was found by Cheapflights users on 1/24. 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 3/1011:59 pm
PDX
-
SJU
2 stops14h 04m
American Airlines
Tue 3/173:40 pm
SJU
-
PDX
1 stop11h 04m
American Airlines
Deal found 1/24$440
This American Airlines deal was found by Cheapflights users on 1/24. 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 4/15:40 am
PDX
-
SJU
1 stop13h 51m
American Airlines
Wed 4/157:25 am
SJU
-
PDX
1 stop16h 34m
American Airlines
Deal found 1/24$455
This United Airlines deal was found by Cheapflights users on 1/25. 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 4/2311:59 pm
PDX
-
SJU
1 stop11h 45m
United Airlines
Wed 4/291:40 pm
SJU
-
PDX
1 stop12h 14m
United Airlines
Deal found 1/25$460
This American Airlines deal was found by Cheapflights users on 1/26. 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 2/169:44 pm
PDX
-
SJU
1 stop15h 08m
American Airlines
Fri 2/207:00 am
SJU
-
PDX
1 stop20h 50m
American Airlines
Deal found 1/26$465
This Southwest deal was found by Cheapflights users on 1/25. 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.
Sat 5/27:40 pm
PDX
-
SJU
2 stops10h 25m
Southwest
Sat 5/99:40 am
SJU
-
PDX
2 stops12h 05m
Southwest
Deal found 1/25$469
This United Airlines deal was found by Cheapflights users on 1/25. 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.
Tue 2/175:05 am
PDX
-
SJU
1 stop9h 20m
United Airlines
Fri 2/208:05 am
SJU
-
PDX
2 stops14h 44m
United Airlines
Deal found 1/25$476
This American Airlines deal was found by Cheapflights users on 1/26. 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 2/2711:52 am
PDX
-
SJU
1 stop13h 32m
American Airlines
Tue 3/32:23 pm
SJU
-
PDX
2 stops13h 54m
American Airlines
Deal found 1/26$478
This CheapOair deal was found by Cheapflights users on 1/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2211:40 pm
PDX
-
SJU
1 stop33h 21m
JetBlue
Fri 5/2912:30 pm
SJU
-
PDX
1 stop12h 55m
JetBlue
Deal found 1/25$485
This Delta deal was found by Cheapflights users on 1/23. 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.
Thu 4/912:30 am
PDX
-
SJU
1 stop10h 45m
Delta
Wed 4/156:15 am
SJU
-
PDX
2 stops12h 52m
Delta
Deal found 1/23$493
This American Airlines deal was found by Cheapflights users on 1/26. 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 5/21:55 pm
PDX
-
SJU
1 stop11h 37m
American Airlines
Sat 5/911:38 am
SJU
-
PDX
2 stops13h 54m
American Airlines
Deal found 1/26$494
This American Airlines deal was found by Cheapflights users on 1/26. 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 4/2111:40 pm
PDX
-
SJU
1 stop12h 02m
American Airlines
Mon 5/43:07 pm
SJU
-
PDX
1 stop11h 34m
American Airlines
Deal found 1/26$497

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 January 26, 2026.

Round-trip from

$440
(American Airlines)

One-way from

$128
(Trip.com)

Popular in

December

Cheapest in

October

Average price

$554
From Portland to Caribbean
One-way flight from Portland to Caribbean
Highest demand for flights based on searches. 11% potential increase in price ($76 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($18 potential savings vs. average RT price).
Average for round-trip flights in January 2026

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 26, 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

Tue 2/17

5:05 am-6:25 pm

1 stop9h 20m

San Juan Luis Munoz Marin Intl

Fri 2/20

8:05 am-6:49 pm

2 stops14h 44m

$476

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 4/23

5:10 am-11:40 pm

2 stops15h 30m

San Juan Luis Munoz Marin Intl

Wed 4/29

8:10 am-7:15 pm

2 stops14h 05m

$478

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 4/24

3:00 pm-8:55 am

2 stops14h 55m

San Juan Luis Munoz Marin Intl

Mon 4/27

2:00 pm-12:25 am

2 stops13h 25m

$493

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 4/21

7:32 pm-11:50 am

2 stops13h 18m

San Juan Luis Munoz Marin Intl

Mon 5/4

6:15 am-5:10 pm

2 stops13h 55m

$503

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 2/25

6:30 am-11:10 pm

2 stops12h 40m

San Juan Luis Munoz Marin Intl

Mon 3/9

1:05 pm-10:35 pm

2 stops12h 30m

$505

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 3/2

8:35 am-12:40 am

2 stops12h 05m

San Juan Luis Munoz Marin Intl

Mon 3/9

1:05 pm-12:45 am

2 stops14h 40m

$505

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 2/23

6:45 am-12:40 am

2 stops13h 55m

San Juan Luis Munoz Marin Intl

Mon 3/2

5:35 am-1:45 pm

2 stops12h 10m

$505

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 4/26

11:55 pm-2:55 pm

2 stops12h 00m

San Juan Luis Munoz Marin Intl

Sun 5/3

1:15 pm-12:05 am

2 stops13h 50m

$513

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 3/1

11:59 pm-3:40 pm

1 stop11h 41m

San Juan Luis Munoz Marin Intl

Tue 3/3

2:05 am-2:48 pm

2 stops16h 43m

$530

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 2/28

9:44 pm-11:40 am

1 stop9h 56m

San Juan Luis Munoz Marin Intl

Wed 3/11

3:01 pm-11:09 pm

1 stop11h 08m

$550

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

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 $188). 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 26, 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.

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

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

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

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

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

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

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

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

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

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

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

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 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, Southwest, and Delta fly from Portland to Caribbean in about 9h 20m. The time it takes to get you to your destination can typically vary by up to 6h 10m. 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 $185 on Delta and JetBlue, respectively.

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

  • 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 $188). 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

Browse thousands of different options on Cheapflights for your next trip

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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.

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 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$184Average$681FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$185Average$371FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$241Average$382FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$327Average$681FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$359Average$703FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$454Average$736FlexibilityNo cancel feeOn-time63%

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