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Caribbean Islands

$169+ 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 2/8. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
ene. 22 — ene. 291
jue. 1/22
jue. 1/29
1 adult, Economy
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Cheap 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 diciembre 23, 2025.

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.
mar. 12/3012:49 amPDX - SJU
1 stop18h 38mAmerican Airlines
mar. 1/66:00 amSJU - PDX
1 stop18h 27mAmerican Airlines
Deal found 12/20$745
This American Airlines deal was found by Cheapflights users on 12/21. 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.
mié. 12/2410:39 pmPDX - SJU
1 stop15h 27mAmerican Airlines
jue. 12/251:30 amSJU - PDX
1 stop13h 30mAmerican Airlines
Deal found 12/21$760
This United Airlines deal was found by Cheapflights users on 12/22. 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.
jue. 12/257:00 amPDX - SJU
1 stop10h 26mUnited Airlines
sáb. 12/2710:15 amSJU - PDX
1 stop13h 28mUnited Airlines
Deal found 12/22$785
This United Airlines deal was found by Cheapflights users on 12/22. 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.
jue. 12/257:00 amPDX - SJU
1 stop10h 26mUnited Airlines
vie. 1/27:00 amSJU - PDX
2 stops16h 01mUnited Airlines
Deal found 12/22$805
This Southwest deal was found by Cheapflights users on 12/22. 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.
lun. 12/298:15 amPDX - SJU
2 stops13h 25mSouthwest
lun. 1/53:30 pmSJU - PDX
2 stops12h 50mSouthwest
Deal found 12/22$840
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/3110:52 pmPDX - SJU
1 stop10h 25mUnited Airlines
lun. 1/52:05 amSJU - PDX
2 stops23h 07mUnited Airlines
Deal found 12/20$845
This American Airlines deal was found by Cheapflights users on 12/22. 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.
vie. 12/2610:21 pmPDX - NAS
1 stop14h 52mAmerican Airlines
dom. 12/286:45 pmNAS - PDX
1 stop9h 14mAmerican Airlines
Deal found 12/22$855
This American Airlines deal was found by Cheapflights users on 12/21. 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.
jue. 12/257:00 amPDX - SJU
1 stop12h 22mAmerican Airlines
mar. 1/66:00 amSJU - PDX
1 stop18h 27mAmerican Airlines
Deal found 12/21$855
This Southwest deal was found by Cheapflights users on 12/22. 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.
jue. 12/256:55 pmPDX - SJU
2 stops11h 50mSouthwest
sáb. 12/275:35 amSJU - PDX
2 stops13h 05mSouthwest
Deal found 12/22$885
This American Airlines deal was found by Cheapflights users on 12/21. 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.
jue. 12/257:00 amPDX - SJU
1 stop12h 22mAmerican Airlines
vie. 1/25:24 amSJU - PDX
1 stop11h 19mAmerican Airlines
Deal found 12/21$905
This Delta deal was found by Cheapflights users on 12/22. 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.
vie. 12/265:25 pmPDX - PLS
2 stops18h 45mDelta
jue. 1/13:50 pmPLS - PDX
2 stops20h 18mDelta
Deal found 12/22$909
This United Airlines deal was found by Cheapflights users on 12/21. 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.
mar. 12/2312:54 pmPDX - SJU
2 stops13h 17mUnited Airlines
lun. 12/293:46 pmSJU - PDX
2 stops22h 15mUnited Airlines
Deal found 12/21$910

Find 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 diciembre 23, 2025.

Round-trip from

$394
(Southwest)

One-way from

$169
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$781
From Portland to Caribbean Islands
Search Deals
One-way flight from Portland to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($77 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 December 2025
Search Deals

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 diciembre 23, 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

mar. 3/10

7:43 pm-12:54 pm

2 stops14h 11m

San Juan Luis Munoz Marin Intl

sáb. 5/2

6:15 am-8:07 pm

2 stops16h 52m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

mar. 1/20

5:00 am-6:25 pm

1 stop9h 25m

San Juan Luis Munoz Marin Intl

vie. 1/23

2:05 am-2:46 pm

2 stops16h 41m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

mar. 1/20

11:01 pm-6:22 pm

1 stop15h 21m

San Juan Luis Munoz Marin Intl

sáb. 1/24

6:00 am-8:27 pm

1 stop18h 27m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

lun. 3/9

7:43 pm-12:07 pm

2 stops13h 24m

San Juan Luis Munoz Marin Intl

mar. 5/5

6:15 am-5:03 pm

2 stops13h 48m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

lun. 1/12

7:00 am-9:00 pm

1 stop10h 00m

San Juan Luis Munoz Marin Intl

vie. 1/16

8:10 am-6:56 pm

2 stops14h 46m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

mar. 3/10

11:59 pm-4:59 pm

2 stops14h 00m

San Juan Luis Munoz Marin Intl

mar. 3/17

6:00 am-11:44 pm

1 stop20h 44m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

mié. 2/18

7:35 pm-4:50 pm

2 stops17h 15m

San Juan Luis Munoz Marin Intl

mié. 2/25

6:15 am-8:55 pm

2 stops18h 40m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

mié. 3/11

7:00 am-11:59 pm

1 stop13h 59m

San Juan Luis Munoz Marin Intl

jue. 4/30

6:15 am-5:03 pm

2 stops13h 48m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

mar. 3/10

5:19 am-11:59 pm

2 stops15h 40m

San Juan Luis Munoz Marin Intl

mar. 5/5

6:15 am-5:03 pm

2 stops13h 48m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

mar. 1/27

6:20 am-11:10 pm

2 stops12h 50m

San Juan Luis Munoz Marin Intl

lun. 2/2

6:10 am-3:40 pm

2 stops13h 30m

$477

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

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, August is the cheapest month in which you can book a flight from Portland to Caribbean Islands (average of $186). Flying from Portland to Caribbean Islands in November is currently the most expensive (average of $399). 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 diciembre 23, 2025.

When flying from Portland to Caribbean Islands, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 15% versus a flight in the morning.

What is the cheapest day to fly from Portland to Caribbean Islands?

Use this chart to determine the cheapest time to fly round-trip from Portland to Caribbean Islands. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Portland to Caribbean Islands flight should consider departing on Sunday afternoons when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 diciembre 23, 2025.
See what other customers who have flown with Southwest, Delta, and United Airlines 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.
Southwest
8.0
Very good
4,253 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,014 reviews
Southwest
8.0
Very good
4,253 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,105 reviews
Southwest
8.0
Very good
4,253 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,054 reviews
Southwest
8.0
Very good
4,253 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,196 reviews
Southwest
8.0
Very good
4,253 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 9h 25m. 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 American Airlines ($143), Delta ($150), and United Airlines ($174).

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

    Most travelers choose Portland - San Juan Luis Munoz Marin Intl, Portland - Saint Thomas Island Cyril E King or Portland - Punta Cana 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, August is the cheapest month in which you can book a flight from Portland to Caribbean Islands (average of $186). Flying from Portland to Caribbean Islands in November is currently the most expensive (average of $399). 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 6 airlines flying from Portland to Caribbean Islands

Discover the top 6 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 diciembre 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$540FlexibilityNo cancel feeOn-time62%
DeltaCheapest$190Average$720FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$243Average$358FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$348Average$701FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$405Average$698FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$444Average$728FlexibilityNo cancel feeOn-time63%

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