HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$190+ 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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Oct 31 — Nov 71
Fri 10/31
Fri 11/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Caribbean Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 October 1, 2025.

Round-trip from

$419
(United Airlines)

One-way from

$190
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$474
From Portland to Caribbean Islands
Search Deals
One-way flight from Portland to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 1, 2025.

This United Airlines deal was found by Cheapflights users on 9/30. 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 10/297:00 amPDX - SJU
1 stop10h 00mUnited Airlines
Wed 11/53:46 pmSJU - PDX
1 stop10h 59mUnited Airlines
Deal found 9/30$419
This Southwest deal was found by Cheapflights users on 9/30. 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 10/296:30 pmPDX - SJU
2 stops11h 35mSouthwest
Wed 11/58:55 amSJU - PDX
2 stops13h 20mSouthwest
Deal found 9/30$439
This United Airlines deal was found by Cheapflights users on 9/29. 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 11/77:10 pmPDX - SJU
2 stops14h 07mUnited Airlines
Tue 11/113:46 pmSJU - PDX
1 stop10h 59mUnited Airlines
Deal found 9/29$449
This Sun Country Air deal was found by Cheapflights users on 9/30. 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 10/1711:59 pmPDX - SJU
1 stop12h 12mSun Country Air
Mon 11/245:15 pmSJU - PDX
1 stop28h 03mSun Country Air
Deal found 9/30$453
This American Airlines deal was found by Cheapflights users on 9/30. 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 12/25:59 pmPDX - SJU
2 stops12h 08mAmerican Airlines
Thu 12/1111:00 amSJU - PDX
2 stops14h 21mAmerican Airlines
Deal found 9/30$457
This Sun Country Air deal was found by Cheapflights users on 9/30. 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 10/1711:59 pmPDX - SJU
1 stop12h 12mSun Country Air
Sat 11/225:15 pmSJU - PDX
1 stop28h 21mSun Country Air
Deal found 9/30$463
This Frontier deal was found by Cheapflights users on 10/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3012:52 pmPDX - SJU
2 stops24h 18mFrontier
Wed 11/51:59 amSJU - PDX
2 stops13h 57mFrontier
Deal found 10/1$464
This Kiwi.com deal was found by Cheapflights users on 9/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/173:53 pmPDX - SJU
2 stops40h 03mMultiple Airlines
Mon 11/245:15 pmSJU - PDX
1 stop28h 03mMultiple Airlines
Deal found 9/30$465
This American Airlines deal was found by Cheapflights users on 9/29. 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 11/2510:45 pmPDX - STI
1 stop12h 47mAmerican Airlines
Tue 12/94:32 pmSTI - PDX
1 stop11h 20mAmerican Airlines
Deal found 9/29$467
This American Airlines deal was found by Cheapflights users on 9/29. 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 10/2211:58 pmPDX - SJU
1 stop11h 10mAmerican Airlines
Fri 10/317:45 amSJU - PDX
1 stop15h 32mAmerican Airlines
Deal found 9/29$473
This Kiwi.com deal was found by Cheapflights users on 9/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/173:53 pmPDX - SJU
2 stops40h 03mMultiple Airlines
Sat 11/225:15 pmSJU - PDX
1 stop28h 21mMultiple Airlines
Deal found 9/30$476
This Southwest deal was found by Cheapflights users on 9/30. 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 11/56:15 amPDX - SJU
2 stops11h 50mSouthwest
Wed 11/122:05 pmSJU - PDX
2 stops12h 30mSouthwest
Deal found 9/30$477

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 October 1, 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 1/20

12:55 am-3:20 pm

1 stop10h 25m

San Juan Luis Munoz Marin Intl

Wed 1/28

3:30 pm-10:39 pm

1 stop11h 09m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 1/20

6:30 am-11:10 pm

2 stops12h 40m

San Juan Luis Munoz Marin Intl

Tue 1/27

6:10 am-3:40 pm

2 stops13h 30m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 10/29

7:00 am-8:00 pm

1 stop10h 00m

San Juan Luis Munoz Marin Intl

Wed 11/5

3:46 pm-10:45 pm

1 stop10h 59m

$419

PortlandSantiago de los Caballeros

PDX - STI

PDXSTI

Portland

Mon 3/9

7:00 am-11:27 pm

1 stop13h 27m

Santiago de los Caballeros

Wed 3/11

6:00 am-9:35 pm

1 stop18h 35m

$467

PortlandSantiago de los Caballeros

PDX - STI

PDXSTI

Portland

Tue 11/25

10:45 pm-3:32 pm

1 stop12h 47m

Santiago de los Caballeros

Tue 12/9

4:32 pm-11:52 pm

1 stop11h 20m

$468

PortlandSantiago de los Caballeros

PDX - STI

PDXSTI

Portland

Sat 1/10

10:15 pm-9:43 pm

2 stops19h 28m

Santiago de los Caballeros

Sat 1/17

4:37 pm-11:45 am

2 stops23h 08m

$472

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 1/18

12:55 am-3:20 pm

1 stop10h 25m

San Juan Luis Munoz Marin Intl

Wed 1/28

2:12 pm-9:35 pm

1 stop11h 23m

$472

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 11/5

6:15 am-10:05 pm

2 stops11h 50m

San Juan Luis Munoz Marin Intl

Thu 11/13

3:30 pm-12:20 am

2 stops12h 50m

$477

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 10/23

7:59 pm-1:12 pm

2 stops14h 13m

San Juan Luis Munoz Marin Intl

Wed 10/29

7:15 am-10:27 pm

2 stops18h 12m

$482

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 10/28

12:40 am-4:25 pm

2 stops12h 45m

San Juan Luis Munoz Marin Intl

Wed 11/5

7:15 am-1:00 pm

1 stop9h 45m

$482

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/29

Showing 1-10 of 60 results
1
2
3
...
6

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 October 1, 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.

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 October 1, 2025.
See what other customers who have flown with Alaska Airlines, Southwest, and Delta from Portland to Caribbean Islands have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,988 reviews

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
10,988 reviews
Alaska Airlines
8.0
Very good
10,988 reviews

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Southwest
8.0
Very good
4,248 reviews
Alaska Airlines
8.0
Very good
10,988 reviews

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Delta
8.0
Very good
7,961 reviews
Alaska Airlines
8.0
Very good
10,988 reviews

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
United Airlines
7.4
Good
8,929 reviews
Alaska Airlines
8.0
Very good
10,988 reviews

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
American Airlines
7.2
Good
11,030 reviews
Alaska Airlines
8.0
Very good
10,988 reviews

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

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.

  • How long is the flight from Portland to Caribbean Islands?

    Departing from Portland to Caribbean Islands will take you 10h. Portland and Caribbean Islands are separated by a distance of 3710 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 Delta ($191), Frontier ($197), and American Airlines ($210).

  • 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 - Nassau 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
Portland to Los Angeles flights
Portland to Las Vegas flights
Portland to Newark flights
Portland to Sky Harbor Intl flights
Portland to San Francisco flights
Portland to John F Kennedy Intl flights
Portland to Santa Ana flights
Portland to Ontario flights
Portland to Honolulu flights
Portland to O'Hare Intl flights
Portland to Cancún flights
Portland to San Diego flights
Portland to Dallas/Fort Worth flights
Portland to Denver flights
Portland to LaGuardia flights
Boise to Los Angeles flights
Portland to Hobby flights
Portland to Orlando flights
Portland to Kahului flights
Portland to George Bush Intcntl flights
Portland to Salt Lake City flights
Portland to Boston flights
Portland to Mexico City flights
Portland to Kailua-Kona flights
Boise to Las Vegas flights
Boise to Seattle flights
Portland to Palm Springs flights
Boise to Denver flights
Portland to Puerto Vallarta flights
Portland to Midway flights
Portland to Cozumel flights
Portland to New Orleans flights
Portland to Atlanta flights
Medford to Seattle flights
Portland to San José del Cabo flights
Boise to Atlanta flights
Portland to San Jose flights
Portland to Dulles Intl flights
Portland to Austin flights
Portland to Miami flights
Eugene to Detroit flights
Portland to Reagan-National flights
Eugene to Denver flights
Portland to Tampa flights
Eugene to Flint flights
Portland to Oakland flights
Portland to Minneapolis flights
Portland to Fort Lauderdale flights
Portland to Detroit flights
Portland to Lihue flights

Top 7 airlines flying from Portland to Caribbean Islands

Discover the top 7 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 October 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$540FlexibilityNo cancel feeOn-time62%
DeltaCheapest$190Average$712FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$248Average$415FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$341Average$708FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$399Average$685FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$431Average$534FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$444Average$728FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.