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Caribbean Islands

$188+ 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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
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 June 18, 2025.

Round-trip from

$375
(FlightHub)

One-way from

$188
(Mytrip)

Popular in

March

Cheapest in

September

Average price

$635
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. 11% potential increase in price ($74 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($22 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 18, 2025.

This FlightHub deal was found by Cheapflights users on 6/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/86:39 pmPDX - SJU
2 stops13h 53mSpirit Airlines
Tue 7/154:43 pmSJU - PDX
2 stops24h 32mSpirit Airlines
Deal found 6/17$375
This FlightHub deal was found by Cheapflights users on 6/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/86:39 pmPDX - STT
2 stops14h 51mSpirit Airlines
Tue 7/151:25 pmSTT - PDX
2 stops22h 53mSpirit Airlines
Deal found 6/18$384
This American Airlines deal was found by Cheapflights users on 6/18. 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.
Mon 9/299:56 pmPDX - SJU
1 stop14h 56mAmerican Airlines
Mon 10/63:05 pmSJU - PDX
1 stop10h 59mAmerican Airlines
Deal found 6/18$399
This Delta deal was found by Cheapflights users on 6/16. 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 8/307:19 amPDX - SJU
1 stop13h 32mDelta
Thu 9/412:50 pmSJU - PDX
1 stop12h 22mDelta
Deal found 6/16$409
This Mytrip deal was found by Cheapflights users on 6/18. 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.
Fri 7/114:37 pmPDX - SJU
3 stops29h 58mMultiple Airlines
Sat 7/191:27 amSJU - PDX
3 stops34h 51mMultiple Airlines
Deal found 6/18$438
This FlightHub deal was found by Cheapflights users on 6/16. 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 7/512:12 pmPDX - PUJ
2 stops22h 58mSpirit Airlines
Sat 7/121:00 pmPUJ - PDX
2 stops23h 18mSpirit Airlines
Deal found 6/16$444
This Mytrip deal was found by Cheapflights users on 6/16. 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 7/219:22 amPDX - STT
3 stops26h 48mMultiple Airlines
Sun 7/2710:43 amSTT - PDX
2 stops25h 35mMultiple Airlines
Deal found 6/16$446
This Southwest deal was found by Cheapflights users on 6/17. 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.
Wed 9/176:40 pmPDX - SJU
2 stops12h 35mSouthwest
Sun 9/215:05 amSJU - PDX
2 stops18h 35mSouthwest
Deal found 6/17$447
This FlightHub deal was found by Cheapflights users on 6/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/273:10 pmPDX - MBJ
2 stops17h 55mSpirit Airlines
Sat 8/212:10 pmMBJ - PDX
2 stops23h 08mSpirit Airlines
Deal found 6/17$450
This United Airlines deal was found by Cheapflights users on 6/17. 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.
Fri 9/123:44 pmPDX - SJU
2 stops17h 16mUnited Airlines
Sat 9/132:00 pmSJU - PDX
1 stop10h 01mUnited Airlines
Deal found 6/17$484
This American Airlines deal was found by Cheapflights users on 6/16. 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 7/712:59 amPDX - NAS
1 stop13h 26mAmerican Airlines
Wed 7/1611:05 amNAS - PDX
1 stop12h 42mAmerican Airlines
Deal found 6/16$485
This United Airlines deal was found by Cheapflights users on 6/18. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/217:35 pmPDX - PUJ
2 stops15h 30mUnited Airlines
Mon 10/271:05 pmPUJ - PDX
1 stop11h 21mUnited Airlines
Deal found 6/18$487

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 June 18, 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

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 7/8

6:39 pm-11:32 am

2 stops13h 53m

San Juan Luis Munoz Marin Intl

Tue 7/15

4:43 pm-2:15 pm

2 stops24h 32m

$375

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Tue 7/8

6:39 pm-12:30 pm

2 stops14h 51m

Saint Thomas Island Cyril E King

Tue 7/15

1:25 pm-9:18 am

2 stops22h 53m

$384

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 9/29

9:56 pm-3:52 pm

1 stop14h 56m

San Juan Luis Munoz Marin Intl

Mon 10/6

3:05 pm-11:04 pm

1 stop10h 59m

$399

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 8/30

7:19 am-11:51 pm

1 stop13h 32m

San Juan Luis Munoz Marin Intl

Thu 9/4

12:50 pm-10:12 pm

1 stop12h 22m

$409

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 7/11

4:37 pm-1:35 am

3 stops29h 58m

San Juan Luis Munoz Marin Intl

Sat 7/19

1:27 am-9:18 am

3 stops34h 51m

$438

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Sat 7/5

12:12 pm-2:10 pm

2 stops22h 58m

Punta Cana

Sat 7/12

1:00 pm-9:18 am

2 stops23h 18m

$444

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Mon 7/21

9:22 am-3:10 pm

3 stops26h 48m

Saint Thomas Island Cyril E King

Sun 7/27

10:43 am-9:18 am

2 stops25h 35m

$446

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 9/17

6:40 pm-10:15 am

2 stops12h 35m

San Juan Luis Munoz Marin Intl

Sun 9/21

5:05 am-8:40 pm

2 stops18h 35m

$447

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Sun 7/27

3:10 pm-11:05 am

2 stops17h 55m

Montego Bay Sangster Intl

Sat 8/2

12:10 pm-9:18 am

2 stops23h 08m

$450

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 9/12

3:44 pm-12:00 pm

2 stops17h 16m

San Juan Luis Munoz Marin Intl

Sat 9/13

2:00 pm-9:01 pm

1 stop10h 01m

$484

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/17

Showing 1-10 of 60 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 June is currently the most expensive (average of $339). 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 June 18, 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 June 18, 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
10,000 reviews

Food

7.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Southwest
8.0
Very good
4,280 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Delta
8.0
Very good
7,964 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
United Airlines
7.4
Good
8,810 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
JetBlue
7.3
Good
2,923 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.

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 American Airlines ($189), JetBlue ($190), and Spirit Airlines ($196).

  • 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 June is currently the most expensive (average of $339). 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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Top 8 airlines flying from Portland to Caribbean Islands

Discover the top 8 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 June 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$380FlexibilityNo cancel feeOn-time62%
DeltaCheapest$218Average$714FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$251Average$363FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$306Average$693FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$328Average$720FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$450Average$713FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$454Average$549FlexibilityNo cancel feeOn-time75%
Sun Country AirCheapest$475Average$737FlexibilityNo cancel feeOn-time83%

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