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Caribbean

$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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Round-trip from

$369
(Delta)

One-way from

$144
(Cheapflightsfares)

Popular in

March

Cheapest in

September

Average price

$515
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. 13% potential increase in price ($81 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 24, 2025.

This Delta deal was found by Cheapflights users on 4/22. 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 8/2210:55 pmPDX - SJU
1 stop11h 15mDelta
Sat 9/67:00 amSJU - PDX
2 stops18h 38mDelta
Deal found 4/22$369
This Mytrip deal was found by Cheapflights users on 4/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/75:40 pmPDX - SJU
2 stops25h 37mSpirit Airlines
Sat 5/101:39 pmSJU - PDX
2 stops26h 03mSpirit Airlines
Deal found 4/23$382
This United Airlines deal was found by Cheapflights users on 4/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1111:20 pmPDX - SJU
1 stop10h 14mUnited Airlines
Fri 8/151:40 pmSJU - PDX
2 stops13h 55mUnited Airlines
Deal found 4/23$400
This JetBlue deal was found by Cheapflights users on 4/22. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1311:35 pmPDX - SJU
1 stop13h 14mJetBlue
Fri 6/2012:55 pmSJU - PDX
1 stop12h 20mJetBlue
Deal found 4/22$412
This Delta deal was found by Cheapflights users on 4/23. 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.
Tue 9/25:45 pmPDX - AUA
2 stops17h 25mDelta
Fri 9/193:25 pmAUA - PDX
2 stops20h 39mDelta
Deal found 4/23$416
This CheapOair deal was found by Cheapflights users on 4/22. 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.
Sat 5/101:37 pmPDX - SJU
2 stops18h 54mMultiple Airlines
Sat 5/174:15 pmSJU - PDX
1 stop25h 39mMultiple Airlines
Deal found 4/22$418
This American Airlines deal was found by Cheapflights users on 4/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/76:07 pmPDX - SJU
2 stops13h 52mAmerican Airlines
Sun 5/186:10 amSJU - PDX
1 stop19h 57mAmerican Airlines
Deal found 4/23$432
This Southwest deal was found by Cheapflights users on 4/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/117:15 pmPDX - SJU
2 stops12h 35mSouthwest
Fri 8/1511:10 amSJU - PDX
2 stops12h 40mSouthwest
Deal found 4/23$443
This Booking.com deal was found by Cheapflights users on 4/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/291:37 pmPDX - STT
2 stops17h 20mSpirit Airlines
Thu 6/1210:47 amSTT - PDX
2 stops27h 30mSpirit Airlines
Deal found 4/22$453
This FlightHub deal was found by Cheapflights users on 4/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/71:37 pmPDX - PUJ
2 stops18h 24mSpirit Airlines
Wed 6/113:22 pmPUJ - PDX
2 stops22h 55mSpirit Airlines
Deal found 4/22$475
This Sun Country Air deal was found by Cheapflights users on 4/22. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/146:36 pmPDX - SJU
1 stop17h 38mSun Country Air
Sat 11/225:15 pmSJU - PDX
1 stop28h 15mSun Country Air
Deal found 4/22$478
This Mytrip deal was found by Cheapflights users on 4/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/291:37 pmPDX - STT
3 stops20h 59mMultiple Airlines
Thu 6/1210:47 amSTT - PDX
2 stops32h 03mMultiple Airlines
Deal found 4/22$484

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 April 24, 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

Fri 8/22

7:20 pm-3:18 pm

2 stops16h 58m

San Juan Luis Munoz Marin Intl

Wed 9/10

7:00 am-11:48 pm

2 stops19h 48m

$369

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 5/7

5:40 pm-10:17 pm

2 stops25h 37m

San Juan Luis Munoz Marin Intl

Sat 5/10

1:39 pm-12:42 pm

2 stops26h 03m

$382

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 8/11

11:20 pm-12:34 pm

1 stop10h 14m

San Juan Luis Munoz Marin Intl

Fri 8/15

1:40 pm-12:35 am

2 stops13h 55m

$400

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 6/13

11:35 pm-3:49 pm

1 stop13h 14m

San Juan Luis Munoz Marin Intl

Fri 6/20

12:55 pm-10:15 pm

1 stop12h 20m

$412

PortlandOranjestad

PDX - AUA

PDXAUA

Portland

Tue 9/2

5:45 pm-2:10 pm

2 stops17h 25m

Oranjestad Reina Beatrix

Fri 9/19

3:25 pm-9:04 am

2 stops20h 39m

$416

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 5/10

1:37 pm-11:31 am

2 stops18h 54m

San Juan Luis Munoz Marin Intl

Sat 5/17

4:15 pm-2:54 pm

1 stop25h 39m

$418

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 5/7

6:07 pm-10:59 am

2 stops13h 52m

San Juan Luis Munoz Marin Intl

Sun 5/18

6:10 am-11:07 pm

1 stop19h 57m

$432

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 8/11

7:15 pm-10:50 am

2 stops12h 35m

San Juan Luis Munoz Marin Intl

Fri 8/15

11:10 am-8:50 pm

2 stops12h 40m

$443

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Thu 5/29

1:37 pm-9:57 am

2 stops17h 20m

Saint Thomas Island Cyril E King

Thu 6/12

10:47 am-11:17 am

2 stops27h 30m

$453

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Sat 6/7

1:37 pm-11:01 am

2 stops18h 24m

Punta Cana

Wed 6/11

3:22 pm-11:17 am

2 stops22h 55m

$475

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 59 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, September is the cheapest month in which you can book a flight from Portland to Caribbean (average of $254). Flying from Portland to Caribbean in December is currently the most expensive (average of $336). 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 April 24, 2025.

When flying from Portland to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 April 24, 2025.
Alaska Airlines
8.0
Very good
9,918 reviews

Food

7.1

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,918 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Food

7.1

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,286 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Food

7.1

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,920 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Food

7.1

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
LATAM Airlines
7.5
Good
1,765 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Food

7.1

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,685 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Food

7.1

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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.

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

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $144. Users have also found prices from $180 and $185 on JetBlue and Delta, 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 - Montego Bay Sangster Intl and Portland - Oranjestad Reina Beatrix.

  • 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, September is the cheapest month in which you can book a flight from Portland to Caribbean (average of $254). Flying from Portland to Caribbean in December is currently the most expensive (average of $336). 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 9 airlines flying from Portland to Caribbean

Discover the top 9 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$223Average$306FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$245Average$365FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$250Average$534FlexibilityNo cancel feeOn-time75%
JetBlueCheapest$288Average$380FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$298Average$681FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$327Average$728FlexibilityNo cancel feeOn-time71%
DeltaCheapest$360Average$702FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$450Average$701FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$475Average$717FlexibilityNo cancel feeOn-time83%

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