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Caribbean

$166+ 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 2/1. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Jan 2 — Jan 91
Fri 1/2
Fri 1/9
1 adult, Economy
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Cheap 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 3, 2025.

This Southwest deal was found by Cheapflights users on 12/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/158:00 amPDX - SJU
2 stops12h 35mSouthwest
Tue 12/2311:35 amSJU - PDX
2 stops14h 05mSouthwest
Deal found 12/1$482
This American Airlines deal was found by Cheapflights users on 12/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/303:02 pmPDX - NAS
1 stop18h 41mAmerican Airlines
Tue 1/62:58 pmNAS - PDX
1 stop11h 48mAmerican Airlines
Deal found 12/1$533
This American Airlines deal was found by Cheapflights users on 12/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1510:15 pmPDX - SJU
1 stop19h 54mAmerican Airlines
Tue 12/2310:25 amSJU - PDX
1 stop18h 34mAmerican Airlines
Deal found 12/1$536
This United Airlines deal was found by Cheapflights users on 11/30. 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.
Tue 12/3011:55 pmPDX - NAS
1 stop12h 27mUnited Airlines
Tue 1/64:25 pmNAS - PDX
2 stops20h 20mUnited Airlines
Deal found 11/30$537
This Delta deal was found by Cheapflights users on 12/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/107:30 pmPDX - SJU
2 stops14h 29mDelta
Thu 12/183:10 pmSJU - PDX
1 stop11h 05mDelta
Deal found 12/1$545
This Delta deal was found by Cheapflights users on 12/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1010:10 pmPDX - MBJ
1 stop11h 54mDelta
Wed 12/172:29 pmMBJ - PDX
1 stop10h 50mDelta
Deal found 12/1$553
This Delta deal was found by Cheapflights users on 12/2. 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 12/155:30 amPDX - SJU
2 stops14h 29mDelta
Wed 12/246:30 amSJU - PDX
2 stops20h 23mDelta
Deal found 12/2$572
This Air Canada deal was found by Cheapflights users on 12/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/97:00 pmPDX - NAS
2 stops14h 55mAir Canada
Tue 12/161:15 pmNAS - PDX
2 stops23h 00mAir Canada
Deal found 12/1$573
This American Airlines deal was found by Cheapflights users on 12/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/510:45 pmPDX - SDQ
1 stop14h 38mAmerican Airlines
Mon 12/224:49 pmSDQ - PDX
1 stop12h 10mAmerican Airlines
Deal found 12/1$577
This American Airlines deal was found by Cheapflights users on 12/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2410:39 pmPDX - NAS
1 stop13h 28mAmerican Airlines
Wed 12/313:10 pmNAS - PDX
1 stop22h 50mAmerican Airlines
Deal found 12/1$580
This Southwest deal was found by Cheapflights users on 12/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/168:00 amPDX - SJU
2 stops12h 35mSouthwest
Tue 12/2311:35 amSJU - PDX
2 stops14h 05mSouthwest
Deal found 12/1$582
This American Airlines deal was found by Cheapflights users on 12/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1310:45 pmPDX - NAS
1 stop8h 34mAmerican Airlines
Tue 12/236:45 pmNAS - PDX
1 stop9h 14mAmerican Airlines
Deal found 12/1$583

Find flight deals from Portland to Caribbean

Keep the following information in mind while searching for Portland to Caribbean flight deals. Data was last updated December 3, 2025.

Round-trip from

$369
(Southwest)

One-way from

$166
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$773
From Portland to Caribbean
Search Deals
One-way flight from Portland to Caribbean
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($63 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($18 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 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 3, 2025.
Use the filters below to find and compare flights from Portland to Caribbean that are best for you.

Fly from

Portland

Fly to

Caribbean

Route

Depart

Return

Price

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 2/5

7:00 am-9:00 pm

1 stop10h 00m

San Juan Luis Munoz Marin Intl

Fri 2/6

8:10 am-6:56 pm

2 stops14h 46m

$414

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 5/3

9:45 pm-1:14 pm

1 stop12h 29m

San Juan Luis Munoz Marin Intl

Sat 5/9

1:10 pm-11:53 pm

2 stops13h 43m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 5/4

5:10 am-11:40 pm

2 stops15h 30m

San Juan Luis Munoz Marin Intl

Wed 5/13

8:20 am-6:30 pm

2 stops13h 10m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 4/7

8:00 am-9:24 pm

1 stop10h 24m

San Juan Luis Munoz Marin Intl

Thu 4/16

1:40 pm-10:52 pm

1 stop12h 12m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 1/21

7:00 am-11:57 pm

1 stop12h 57m

San Juan Luis Munoz Marin Intl

Tue 1/27

3:20 pm-12:17 am

2 stops12h 57m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 1/18

7:00 am-11:57 pm

1 stop12h 57m

San Juan Luis Munoz Marin Intl

Fri 1/23

3:55 pm-10:45 pm

1 stop10h 50m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 5/4

7:40 pm-12:50 pm

2 stops14h 10m

San Juan Luis Munoz Marin Intl

Thu 5/7

6:15 am-1:14 pm

1 stop9h 59m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 1/19

5:15 pm-2:31 pm

2 stops17h 16m

San Juan Luis Munoz Marin Intl

Wed 1/28

3:20 pm-12:17 am

2 stops12h 57m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 3/8

6:57 pm-12:17 pm

2 stops14h 20m

San Juan Luis Munoz Marin Intl

Tue 3/17

2:46 pm-11:11 pm

1 stop11h 25m

$447

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 2/5

7:00 am-9:00 pm

1 stop10h 00m

San Juan Luis Munoz Marin Intl

Sat 2/14

7:45 am-6:55 pm

2 stops15h 10m

$448

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/3

Showing 1-10 of 60 results
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6

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.

Cheapflights Insights

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

What is the cheapest month to book a flight from Portland to Caribbean?

Currently, August is the cheapest month in which you can book a flight from Portland to Caribbean (average of $186). Flying from Portland to Caribbean in November is currently the most expensive (average of $388). 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 3, 2025.

One of the essential ways to save on airfare from Portland to Caribbean is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 15% on airfare.

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

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

Travelers seeking maximum savings on their Portland to Caribbean 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

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 3, 2025.
Read through reviews of airlines operating flights from Portland to Caribbean, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,254 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
8.0
Very good
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Delta
7.9
Good
8,011 reviews
Southwest
8.0
Very good
4,254 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
United Airlines
7.4
Good
9,065 reviews
Southwest
8.0
Very good
4,254 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
American Airlines
7.2
Good
11,044 reviews
Southwest
8.0
Very good
4,254 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Spirit Airlines
6.3
Okay
8,161 reviews
Southwest
8.0
Very good
4,254 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

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.

  • How long is the flight from Portland to Caribbean?

    Airlines like United Airlines, Delta, and American Airlines fly from Portland to Caribbean in about 10h. The time it takes to get you to your destination can typically vary by up to 4h 44m. Portland and Caribbean are separated by a distance of 3710 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Portland to Caribbean one-way?

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $143. Users have also found prices from $174 and $184 on United Airlines and Delta, 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 - Saint Thomas Island Cyril E King and Portland - Nassau Intl.

  • 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, August is the cheapest month in which you can book a flight from Portland to Caribbean (average of $186). Flying from Portland to Caribbean in November is currently the most expensive (average of $388). 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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See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Portland to Caribbean

Discover the top 6 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 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$540FlexibilityNo cancel feeOn-time62%
DeltaCheapest$190Average$709FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$243Average$330FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$347Average$710FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$399Average$687FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$444Average$725FlexibilityNo cancel feeOn-time63%

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