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$137+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
1 adult, Economy
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Cheap flight deals from Portland to Caribbean

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to Caribbean (0CB). 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 18, 2024.

Round-trip from

$321
(FlightHub)

One-way from

$137
(CheapOair)
From Portland to Caribbean
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One-way flight from Portland to Caribbean
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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 December 18, 2024.

This Delta deal was found by Cheapflights users on 12/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/197:00 amPDX - SJU
1 stop13h 41mDelta
Sat 1/187:00 amSJU - PDX
2 stops17h 35mDelta
Deal found 12/17$579
This CheapOair deal was found by Cheapflights users on 12/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/317:48 pmPDX - SJU
2 stops17h 52mSpirit Airlines
Sun 1/59:40 pmSJU - PDX
2 stops24h 42mSpirit Airlines
Deal found 12/17$678
This United deal was found by Cheapflights users on 12/18. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/185:00 amPDX - SJU
1 stop9h 25mUnited Airlines
Fri 1/172:05 amSJU - PDX
2 stops20h 57mUnited Airlines
Deal found 12/18$733
This American Airlines deal was found by Cheapflights users on 12/18. 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.
Wed 12/2510:42 pmPDX - SJU
1 stop9h 18mAmerican Airlines
Wed 1/16:25 amSJU - PDX
1 stop15h 20mAmerican Airlines
Deal found 12/18$752
This Mytrip deal was found by Cheapflights users on 12/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2311:59 pmPDX - SJU
2 stops21h 36mMultiple Airlines
Fri 12/272:45 amSJU - PDX
2 stops24h 08mMultiple Airlines
Deal found 12/18$803
This Cheapflightsfares deal was found by Cheapflights users on 12/17. 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 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 12/17$888
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/2310:42 pmPDX - PUJ
1 stop13h 57mAmerican Airlines
Fri 12/273:06 pmPUJ - PDX
1 stop12h 32mAmerican Airlines
Deal found 12/17$933
This Sun Country Air deal was found by Cheapflights users on 12/17. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2311:59 pmPDX - PUJ
1 stop11h 02mSun Country Air
Fri 12/274:05 pmPUJ - PDX
1 stop29h 59mSun Country Air
Deal found 12/17$972
This United Airlines deal was found by Cheapflights users on 12/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/227:11 pmPDX - MBJ
2 stops15h 49mUnited Airlines
Sun 12/293:20 pmMBJ - PDX
2 stops25h 20mUnited Airlines
Deal found 12/17$972
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Thu 12/1912:59 amPDX - MBJ
1 stop13h 05mAmerican Airlines
Sun 12/224:00 pmMBJ - PDX
1 stop9h 57mAmerican Airlines
Deal found 12/17$993
This American Airlines deal was found by Cheapflights users on 12/18. 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.
Wed 12/2510:42 pmPDX - BGI
1 stop12h 58mAmerican Airlines
Mon 12/307:20 amBGI - PDX
1 stop20h 18mAmerican Airlines
Deal found 12/18$1,000
This Southwest deal was found by Cheapflights users on 12/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/207:10 pmPDX - MBJ
2 stops17h 10mSouthwest
Sun 12/221:45 pmMBJ - PDX
2 stops13h 45mSouthwest
Deal found 12/17$1,005

Find flights from Portland to Caribbean within your budget

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 December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Fri 1/31

10:16 am-1:48 pm

2 stops23h 32m

Saint Thomas Island Cyril E King

Sun 2/9

11:51 am-9:21 am

2 stops25h 30m

$321

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 2/18

10:16 am-5:19 pm

2 stops27h 03m

San Juan Luis Munoz Marin Intl

Sun 2/23

6:14 pm-9:21 am

2 stops19h 07m

$378

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 2/1

10:48 pm-12:56 pm

1 stop10h 08m

San Juan Luis Munoz Marin Intl

Wed 2/5

7:45 am-7:02 pm

2 stops15h 17m

$382

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 1/25

10:45 pm-12:30 pm

1 stop9h 45m

San Juan Luis Munoz Marin Intl

Sat 2/8

6:15 am-11:36 pm

1 stop21h 21m

$386

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Thu 1/9

6:40 pm-12:39 pm

2 stops37h 59m

Punta Cana

Wed 1/15

6:10 pm-9:45 am

2 stops43h 35m

$407

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 1/9

7:05 am-11:59 pm

1 stop12h 54m

San Juan Luis Munoz Marin Intl

Sat 1/18

7:00 am-8:35 pm

2 stops17h 35m

$424

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 1/30

8:30 am-1:48 pm

1 stop25h 18m

San Juan Luis Munoz Marin Intl

Sun 2/2

6:36 pm-4:35 pm

2 stops25h 59m

$430

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 4/30

11:10 pm-4:09 pm

1 stop13h 59m

San Juan Luis Munoz Marin Intl

Sat 5/31

1:35 pm-9:55 pm

1 stop11h 20m

$434

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 3/4

6:50 am-12:40 am

2 stops13h 50m

San Juan Luis Munoz Marin Intl

Mon 3/10

5:35 am-5:10 pm

2 stops14h 35m

$445

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Thu 1/30

10:45 pm-12:27 pm

1 stop9h 42m

Saint Thomas Island Cyril E King

Sun 2/9

1:19 pm-11:36 pm

1 stop14h 17m

$458

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

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.

Travel insights for flights from Portland to Caribbean

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

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 March is currently the most expensive (average of $334). 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 December 18, 2024.

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 December 18, 2024.
Southwest
8.1
Very good
4,848 reviews

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

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
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

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
9,554 reviews
Southwest
8.1
Very good
4,848 reviews

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

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
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

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
1,721 reviews
Southwest
8.1
Very good
4,848 reviews

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

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
1,879 reviews
Southwest
8.1
Very good
4,848 reviews

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

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. 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 $137. Users have also found prices from $174 and $208 on American Airlines and Southwest, 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 - Punta Cana and Portland - Saint Thomas Island Cyril E King.

  • 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 March is currently the most expensive (average of $334). 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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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 December 18, 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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