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Caribbean Islands

$151+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Apr 13 — Apr 201
Sun 4/13
Sun 4/20
1 adult, Economy
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Cheap flight deals from Portland to Caribbean Islands

Keep the following information in mind while searching for Portland to Caribbean Islands flight deals. Data was last updated April 8, 2025.

Round-trip from

$348
(Booking.com)

One-way from

$151
(Priceline)

Popular in

March

Cheapest in

September

Average price

$515
From Portland to Caribbean Islands
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One-way flight from Portland to Caribbean Islands
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Highest demand for flights based on searches. 12% potential increase in price ($78 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 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 April 8, 2025.

This Booking.com deal was found by Cheapflights users on 4/7. 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.
Sat 5/175:40 pmPDX - STT
2 stops13h 17mSpirit Airlines
Thu 5/2210:52 amSTT - PDX
2 stops28h 50mSpirit Airlines
Deal found 4/7$348
This Delta deal was found by Cheapflights users on 4/6. 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.
Sat 5/37:00 amPDX - SJU
1 stop13h 48mDelta
Wed 5/71:12 pmSJU - PDX
1 stop13h 03mDelta
Deal found 4/6$369
This Mytrip deal was found by Cheapflights users on 4/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/292:32 pmPDX - SJU
3 stops30h 07mSpirit Airlines
Sun 5/42:12 amSJU - PDX
3 stops38h 25mSpirit Airlines
Deal found 4/6$370
This CheapOair deal was found by Cheapflights users on 4/7. 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 5/105:40 pmPDX - SJU
2 stops14h 51mMultiple Airlines
Sat 5/174:15 pmSJU - PDX
1 stop25h 39mMultiple Airlines
Deal found 4/7$403
This Delta deal was found by Cheapflights users on 4/7. 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 9/27:55 pmPDX - AUA
2 stops15h 15mDelta
Fri 9/193:25 pmAUA - PDX
2 stops20h 39mDelta
Deal found 4/7$416
This FlightHub deal was found by Cheapflights users on 4/7. 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.
Wed 5/71:37 pmPDX - PUJ
2 stops18h 24mSpirit Airlines
Fri 5/163:22 pmPUJ - PDX
2 stops24h 20mSpirit Airlines
Deal found 4/7$432
This American Airlines deal was found by Cheapflights users on 4/8. 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 4/2610:34 pmPDX - SJU
1 stop11h 02mAmerican Airlines
Thu 5/16:21 amSJU - PDX
1 stop20h 07mAmerican Airlines
Deal found 4/8$432
This Booking.com deal was found by Cheapflights users on 4/7. 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.
Sat 5/101:37 pmPDX - MBJ
2 stops19h 25mSpirit Airlines
Thu 5/2912:07 pmMBJ - PDX
2 stops26h 35mSpirit Airlines
Deal found 4/7$440
This United Airlines deal was found by Cheapflights users on 4/6. 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.
Mon 5/510:47 pmPDX - SJU
1 stop11h 58mUnited Airlines
Tue 5/61:05 amSJU - PDX
2 stops16h 49mUnited Airlines
Deal found 4/6$454
This JetBlue deal was found by Cheapflights users on 4/8. 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.
Thu 6/1211:35 pmPDX - SJU
1 stop14h 05mJetBlue
Tue 6/1712:35 pmSJU - PDX
1 stop12h 35mJetBlue
Deal found 4/8$464
This American Airlines deal was found by Cheapflights users on 4/7. 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 4/2810:00 pmPDX - NAS
1 stop12h 40mAmerican Airlines
Mon 5/57:45 amNAS - PDX
1 stop18h 22mAmerican Airlines
Deal found 4/7$465
This Delta deal was found by Cheapflights users on 4/7. 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 9/227:55 pmPDX - PUJ
2 stops15h 42mDelta
Thu 10/24:02 pmPUJ - PDX
2 stops20h 02mDelta
Deal found 4/7$469

Cheapflights Fare Finder

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 April 8, 2025.
Use the filters below to find and compare flights from Portland to Caribbean Islands that are best for you.

Fly from

Portland

Fly to

Caribbean Islands

Route

Depart

Return

Price

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Sat 5/17

5:40 pm-9:57 am

2 stops13h 17m

Saint Thomas Island Cyril E King

Thu 5/22

10:52 am-12:42 pm

2 stops28h 50m

$348

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 5/3

7:00 am-11:48 pm

1 stop13h 48m

San Juan Luis Munoz Marin Intl

Sat 5/10

1:12 pm-11:15 pm

1 stop13h 03m

$369

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 4/29

2:32 pm-11:39 pm

3 stops30h 07m

San Juan Luis Munoz Marin Intl

Sun 5/4

2:12 am-1:37 pm

3 stops38h 25m

$370

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 5/10

5:40 pm-11:31 am

2 stops14h 51m

San Juan Luis Munoz Marin Intl

Sat 5/17

4:15 pm-2:54 pm

1 stop25h 39m

$403

PortlandOranjestad

PDX - AUA

PDXAUA

Portland

Tue 9/2

7:55 pm-2:10 pm

2 stops15h 15m

Oranjestad Reina Beatrix

Fri 9/19

3:25 pm-9:04 am

2 stops20h 39m

$416

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 4/26

10:34 pm-12:36 pm

1 stop11h 02m

San Juan Luis Munoz Marin Intl

Thu 5/1

6:21 am-11:28 pm

1 stop20h 07m

$432

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Wed 5/7

1:37 pm-11:01 am

2 stops18h 24m

Punta Cana

Fri 5/16

3:22 pm-12:42 pm

2 stops24h 20m

$432

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Sat 5/10

1:37 pm-11:02 am

2 stops19h 25m

Montego Bay Sangster Intl

Thu 5/29

12:07 pm-12:42 pm

2 stops26h 35m

$440

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 5/5

10:47 pm-1:45 pm

1 stop11h 58m

San Juan Luis Munoz Marin Intl

Tue 5/6

1:05 am-2:54 pm

2 stops16h 49m

$454

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 6/12

11:35 pm-4:40 pm

1 stop14h 05m

San Juan Luis Munoz Marin Intl

Tue 6/17

12:35 pm-10:10 pm

1 stop12h 35m

$464

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/6

Showing 1-10 of 50 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.

Cheapflights Insights

Everything you need to know about your flight from Portland to Caribbean Islands

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 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 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 April 8, 2025.

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 April 8, 2025.
To help decide which airline to fly from Portland to Caribbean Islands, see what other customers have to say about Alaska Airlines, Southwest and Delta. 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.
Alaska Airlines
8.0
Very good
9,843 reviews

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.1

Overall

8.0

Food

7.1

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
9,843 reviews
Alaska Airlines
8.0
Very good
9,843 reviews

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.1

Overall

8.0

Food

7.1

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
4,277 reviews
Alaska Airlines
8.0
Very good
9,843 reviews

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.1

Overall

8.0

Food

7.1

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
7,901 reviews
Alaska Airlines
8.0
Very good
9,843 reviews

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.1

Overall

8.0

Food

7.1

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
8,629 reviews
Alaska Airlines
8.0
Very good
9,843 reviews

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.1

Overall

8.0

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
JetBlue
7.3
Good
2,923 reviews
Alaska Airlines
8.0
Very good
9,843 reviews

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.1

Overall

8.0

Food

7.1

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 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 ($151), Delta ($179), and American Airlines ($185).

  • 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 - Montego Bay Sangster Intl 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 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 Islands

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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 April 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$367FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$242Average$524FlexibilityNo cancel feeOn-time75%
Spirit AirlinesCheapest$245Average$365FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$288Average$382FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$298Average$686FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$327Average$732FlexibilityNo cancel feeOn-time71%
DeltaCheapest$356Average$698FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$450Average$713FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$475Average$717FlexibilityNo cancel feeOn-time83%

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