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Caribbean

$139+ 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 11/22. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Cheap flight deals from Portland to Caribbean

Keep the following information in mind while searching for Portland to Caribbean flight deals. Data was last updated November 13, 2025.

Round-trip from

$375
(Southwest)

One-way from

$139
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$612
From Portland to Caribbean
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One-way flight from Portland to Caribbean
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Highest demand for flights based on searches. 9% potential increase in price ($61 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find 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 November 13, 2025.

This Southwest deal was found by Cheapflights users on 11/11. 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 12/86:55 pmPDX - SJU
2 stops11h 30mSouthwest
Fri 12/123:30 pmSJU - PDX
2 stops12h 50mSouthwest
Deal found 11/11$375
This Southwest deal was found by Cheapflights users on 11/12. 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 12/108:00 amPDX - SJU
2 stops12h 35mSouthwest
Sat 12/135:40 amSJU - PDX
2 stops14h 50mSouthwest
Deal found 11/12$397
This American Airlines deal was found by Cheapflights users on 11/12. 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 12/610:15 pmPDX - SJU
1 stop19h 50mAmerican Airlines
Mon 12/87:00 amSJU - PDX
1 stop18h 24mAmerican Airlines
Deal found 11/12$414
This Delta deal was found by Cheapflights users on 11/12. 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 12/87:30 pmPDX - SJU
2 stops14h 29mDelta
Thu 12/117:00 amSJU - PDX
2 stops14h 43mDelta
Deal found 11/12$419
This Southwest deal was found by Cheapflights users on 11/12. 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 12/156:55 pmPDX - SJU
2 stops11h 30mSouthwest
Thu 12/186:40 amSJU - PDX
2 stops12h 25mSouthwest
Deal found 11/12$435
This Southwest deal was found by Cheapflights users on 11/11. 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.
Thu 12/118:00 amPDX - SJU
2 stops12h 35mSouthwest
Thu 12/1811:55 amSJU - PDX
2 stops16h 25mSouthwest
Deal found 11/11$444
This American Airlines deal was found by Cheapflights users on 11/12. 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 12/1310:15 pmPDX - SJU
1 stop10h 50mAmerican Airlines
Tue 12/232:31 pmSJU - PDX
1 stop14h 28mAmerican Airlines
Deal found 11/12$457
This American Airlines deal was found by Cheapflights users on 11/11. 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 12/25:30 amPDX - SJU
2 stops15h 14mAmerican Airlines
Tue 12/912:49 pmSJU - PDX
1 stop15h 03mAmerican Airlines
Deal found 11/11$473
This Delta deal was found by Cheapflights users on 11/11. 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 12/135:15 pmPDX - SJU
2 stops15h 43mDelta
Thu 12/187:00 amSJU - PDX
2 stops21h 15mDelta
Deal found 11/11$477
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Thu 12/1112:51 pmPDX - SJU
2 stops17h 04mMultiple Airlines
Thu 12/185:14 pmSJU - PDX
1 stop33h 39mMultiple Airlines
Deal found 11/11$478
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Sun 12/147:26 pmPDX - SJU
2 stops47h 59mMultiple Airlines
Mon 12/225:02 pmSJU - PDX
1 stop28h 12mMultiple Airlines
Deal found 11/11$481
This Delta deal was found by Cheapflights users on 11/13. 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.
Sun 11/2311:15 pmPDX - SJU
1 stop10h 55mDelta
Thu 12/113:10 pmSJU - PDX
1 stop11h 00mDelta
Deal found 11/13$482

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 November 13, 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

Wed 12/10

5:00 am-10:05 pm

2 stops13h 05m

San Juan Luis Munoz Marin Intl

Thu 12/18

11:55 am-12:20 am

2 stops16h 25m

$375

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 2/3

6:45 am-12:35 am

2 stops13h 50m

San Juan Luis Munoz Marin Intl

Tue 2/10

5:40 am-3:45 pm

2 stops14h 05m

$375

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 12/10

8:00 am-12:35 am

2 stops12h 35m

San Juan Luis Munoz Marin Intl

Wed 12/17

11:20 am-9:25 pm

2 stops14h 05m

$397

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 12/8

7:00 am-9:26 pm

1 stop10h 26m

San Juan Luis Munoz Marin Intl

Fri 12/12

2:25 pm-9:15 pm

1 stop10h 50m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 1/25

7:00 am-8:57 pm

1 stop9h 57m

San Juan Luis Munoz Marin Intl

Thu 1/29

7:00 am-5:35 pm

2 stops14h 35m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 1/31

5:23 am-11:59 pm

2 stops14h 36m

San Juan Luis Munoz Marin Intl

Thu 2/5

2:15 pm-12:17 am

2 stops14h 02m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 12/8

7:30 pm-1:59 pm

2 stops14h 29m

San Juan Luis Munoz Marin Intl

Thu 12/11

7:00 am-5:43 pm

2 stops14h 43m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 2/2

7:45 am-12:55 pm

2 stops25h 10m

San Juan Luis Munoz Marin Intl

Tue 2/3

3:46 pm-12:33 pm

2 stops24h 47m

$458

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 1/19

3:50 pm-4:36 pm

2 stops20h 46m

San Juan Luis Munoz Marin Intl

Tue 1/27

2:05 am-11:06 pm

2 stops25h 01m

$458

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

$468

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 60 results
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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 December is currently the most expensive (average of $412). 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 November 13, 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 afternoon tend to be the most expensive. A flight at noon could potentially save you up to 13% 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 November 13, 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
4,242 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
8,007 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,017 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,051 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,139 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 Southwest, United Airlines, and Delta fly from Portland to Caribbean in about 9h 57m. The time it takes to get you to your destination can typically vary by up to 3h 08m. 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 Frontier. According to our data, you can fly for as low as $189. Users have also found prices from $210 and $253 on American 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 December is currently the most expensive (average of $412). 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

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Portland to Caribbean

Discover the top 7 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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$540FlexibilityNo cancel feeOn-time62%
DeltaCheapest$190Average$708FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$248Average$415FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$343Average$713FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$400Average$692FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$431Average$587FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$444Average$726FlexibilityNo cancel feeOn-time63%

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