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Caribbean Islands

$204+ Cheap flights from Portland (PDX) to Caribbean Islands

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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Dec 26 — Jan 21
Thu 12/26
Thu 1/2
1 adult, Economy
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Cheap flight deals from Portland to Caribbean Islands

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to Caribbean Islands (zzEPX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 21, 2024.

Round-trip from

$323
(FlightHub)

One-way from

$204
(Booking.com)
From Portland to Caribbean Islands
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One-way flight from Portland to Caribbean Islands
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Find flight deals from Portland to Caribbean Islands

Cheapest flights from Portland to Caribbean Islands
Explore the most affordable flight options available from Portland to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 21, 2024.

This American Airlines deal was found by Cheapflights users on 12/20. 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 12/2410:42 pmPDX - NAS
1 stop12h 33mAmerican Airlines
Thu 12/263:10 pmNAS - PDX
1 stop10h 47mAmerican Airlines
Deal found 12/20$643
This Cheapflightsfares deal was found by Cheapflights users on 12/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/246:30 pmPDX - SJU
1 stop15h 41mSun Country Air
Mon 12/305:20 pmSJU - PDX
1 stop20h 01mSun Country Air
Deal found 12/20$665
This Delta deal was found by Cheapflights users on 12/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/257:15 amPDX - NAS
1 stop11h 30mDelta
Mon 12/302:51 pmNAS - PDX
1 stop10h 24mDelta
Deal found 12/19$673
This American Airlines deal was found by Cheapflights users on 12/20. 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 12/2410:42 pmPDX - SJU
1 stop10h 53mAmerican Airlines
Sun 12/297:05 amSJU - PDX
1 stop20h 33mAmerican Airlines
Deal found 12/20$684
This United Airlines deal was found by Cheapflights users on 12/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2511:59 pmPDX - NAS
1 stop10h 34mUnited Airlines
Tue 12/3112:55 pmNAS - PDX
1 stop10h 50mUnited Airlines
Deal found 12/19$693
This FlightHub deal was found by Cheapflights users on 12/20. 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.
Tue 12/247:48 pmPDX - SJU
2 stops25h 47mMultiple Airlines
Mon 12/305:20 pmSJU - PDX
1 stop20h 01mMultiple Airlines
Deal found 12/20$724
This FlightHub deal was found by Cheapflights users on 12/20. 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.
Mon 12/236:44 pmPDX - PUJ
1 stop16h 17mSun Country Air
Wed 12/254:05 pmPUJ - PDX
1 stop20h 16mSun Country Air
Deal found 12/20$790
This Gotogate deal was found by Cheapflights users on 12/20. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/309:14 pmPDX - SDQ
2 stops35h 51mFrontier
Sun 1/58:55 pmSDQ - PDX
2 stops23h 04mFrontier
Deal found 12/20$793
This Mytrip deal was found by Cheapflights users on 12/20. 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.
Tue 12/247:48 pmPDX - SJU
2 stops25h 47mSpirit Airlines
Mon 1/64:14 pmSJU - PDX
3 stops30h 39mSpirit Airlines
Deal found 12/20$798
This Southwest deal was found by Cheapflights users on 12/20. 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 12/216:25 pmPDX - PLS
2 stops17h 35mSouthwest
Sat 12/283:20 pmPLS - PDX
2 stops20h 05mSouthwest
Deal found 12/20$883
This Delta deal was found by Cheapflights users on 12/20. 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.
Mon 12/237:00 amPDX - SJU
1 stop15h 18mDelta
Mon 1/62:11 pmSJU - PDX
2 stops13h 43mDelta
Deal found 12/20$884
This Southwest deal was found by Cheapflights users on 12/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/255:50 amPDX - SJU
2 stops14h 40mSouthwest
Tue 1/76:00 amSJU - PDX
2 stops15h 15mSouthwest
Deal found 12/19$894

Find flights from Portland to Caribbean Islands within your budget

Customize your flight search to find flights from Portland to Caribbean Islands 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 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Thu 1/30

5:30 pm-1:48 pm

2 stops16h 18m

Saint Thomas Island Cyril E King

Sun 2/9

11:51 am-9:21 am

2 stops25h 30m

$323

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 2/18

10:16 am-5:01 pm

2 stops26h 45m

San Juan Luis Munoz Marin Intl

Sun 2/23

5:56 pm-9:21 am

2 stops19h 25m

$381

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 1/13

5:31 am-12:04 am

2 stops14h 33m

San Juan Luis Munoz Marin Intl

Sat 1/25

6:15 am-4:51 pm

2 stops14h 36m

$386

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 4/30

5:20 am-10:30 pm

2 stops14h 10m

San Juan Luis Munoz Marin Intl

Tue 5/6

6:05 am-6:50 pm

2 stops15h 45m

$420

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 2/20

7:05 am-11:59 pm

1 stop12h 54m

San Juan Luis Munoz Marin Intl

Thu 2/27

2:11 pm-11:58 pm

2 stops13h 47m

$424

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 1/12

10:48 pm-12:47 pm

1 stop9h 59m

San Juan Luis Munoz Marin Intl

Mon 1/27

2:05 am-1:50 pm

2 stops15h 45m

$438

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Mon 1/13

5:30 pm-12:10 pm

2 stops15h 40m

Montego Bay Sangster Intl

Sat 1/18

2:49 pm-9:21 am

2 stops21h 32m

$446

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Sat 1/11

10:45 pm-12:27 pm

1 stop9h 42m

Saint Thomas Island Cyril E King

Sat 1/18

6:31 pm-11:06 am

2 stops20h 35m

$458

PortlandNassau

PDX - NAS

PDXNAS

Portland

Sat 1/25

1:08 pm-11:53 am

2 stops19h 45m

Nassau Intl

Wed 1/29

12:55 pm-8:37 pm

1 stop10h 42m

$471

PortlandNassau

PDX - NAS

PDXNAS

Portland

Tue 1/21

10:45 pm-11:51 am

1 stop10h 06m

Nassau Intl

Thu 1/30

12:32 pm-11:05 pm

2 stops13h 33m

$476

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/20

Showing 1-10 of 52 results
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Best time to book a flight from Portland to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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.

Travel insights for flights from Portland to Caribbean Islands

Get recent, data-driven insights about flights from Portland to Caribbean Islands including ideal travel times, pricing trends, and more.

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

Currently, September is the cheapest month in which you can book a flight from Portland to Caribbean Islands (average of $254). Flying from Portland to Caribbean Islands in March is currently the most expensive (average of $380). 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 EPX?

Find hourly flight availability from Portland to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 21, 2024.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Portland to Caribbean Islands as you normally would.

Rainfall in Caribbean Islands by month

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

In terms of precipitation, rainfall in Caribbean Islands 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 Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

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

If weather is an important factor for your trip to Caribbean Islands, 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 Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated December 21, 2024.
To help decide which airline to fly from Portland to Caribbean Islands, see what other customers have to say about Southwest, United Airlines and Alaska Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,814 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,814 reviews
Southwest
8.1
Very good
4,814 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,540 reviews
Southwest
8.1
Very good
4,814 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,597 reviews
Southwest
8.1
Very good
4,814 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Copa Airlines
7.7
Good
1,717 reviews
Southwest
8.1
Very good
4,814 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

LATAM Airlines
7.5
Good
1,873 reviews
Southwest
8.1
Very good
4,814 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.2

Entertainment

7.7

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

Find useful and relevant information for your journey from Portland to Caribbean Islands. 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 Islands?

    Located just 6.0 mi from the city center, Portland (PDX) is the airport most travelers will use when flying to Caribbean Islands from Portland.

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

    The cheapest airlines for a one-way flight from Portland to Caribbean Islands are Spirit Airlines ($204), American Airlines ($227), and Delta ($237).

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

    Most travelers choose Portland - San Juan Luis Munoz Marin Intl, Portland - Punta Cana or Portland - Saint Thomas Island Cyril E King when deciding on the best route from Portland to Caribbean Islands.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Portland to Caribbean Islands (average of $254). Flying from Portland to Caribbean Islands in March is currently the most expensive (average of $380). 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.

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Top 9 airlines flying from Portland to Caribbean Islands

Discover the top 9 airlines that operate flights from Portland to Caribbean Islands. 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 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$348FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$217Average$1,713FlexibilityNo cancel feeOn-time75%
Spirit AirlinesCheapest$225Average$362FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$281Average$655FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$288Average$569FlexibilityNo cancel feeOn-time62%
DeltaCheapest$305Average$660FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$325Average$677FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$504Average$864FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$507Average$717FlexibilityNo cancel feeOn-time83%
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