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$210+ 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 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
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 October 28, 2025.

Round-trip from

$372
(Frontier)

One-way from

$210
(Delta)

Popular in

December

Cheapest in

October

Average price

$476
From Portland to Caribbean
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One-way flight from Portland to Caribbean
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($57 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 28, 2025.

This Frontier deal was found by Cheapflights users on 10/27. 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.
Sat 11/1512:52 pmPDX - SJU
2 stops21h 50mFrontier
Thu 11/203:59 amSJU - PDX
2 stops13h 09mFrontier
Deal found 10/27$372
This Southwest deal was found by Cheapflights users on 10/26. 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 12/96:15 amPDX - SJU
2 stops13h 05mSouthwest
Tue 12/168:55 amSJU - PDX
2 stops14h 25mSouthwest
Deal found 10/26$375
This Southwest deal was found by Cheapflights users on 10/27. 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 12/28:00 amPDX - SJU
2 stops12h 35mSouthwest
Wed 12/108:55 amSJU - PDX
2 stops13h 20mSouthwest
Deal found 10/27$397
This Frontier deal was found by Cheapflights users on 10/26. 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.
Mon 11/37:29 pmPDX - SJU
2 stops18h 25mFrontier
Fri 11/72:11 amSJU - PDX
2 stops13h 45mFrontier
Deal found 10/26$413
This Frontier deal was found by Cheapflights users on 10/28. 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 11/1312:52 pmPDX - SJU
2 stops23h 18mFrontier
Thu 11/201:57 pmSJU - PDX
2 stops22h 07mFrontier
Deal found 10/28$414
This Frontier deal was found by Cheapflights users on 10/26. 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.
Mon 11/107:29 pmPDX - SJU
2 stops18h 25mFrontier
Thu 11/132:11 amSJU - PDX
2 stops13h 45mFrontier
Deal found 10/26$418
This American Airlines deal was found by Cheapflights users on 10/26. 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.
Thu 12/410:15 pmPDX - SJU
1 stop19h 54mAmerican Airlines
Wed 12/1011:00 amSJU - PDX
1 stop16h 52mAmerican Airlines
Deal found 10/26$419
This Frontier deal was found by Cheapflights users on 10/28. 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.
Fri 11/73:26 pmPDX - SJU
2 stops16h 50mFrontier
Fri 11/142:11 amSJU - PDX
2 stops13h 45mFrontier
Deal found 10/28$420
This American Airlines deal was found by Cheapflights users on 10/26. 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 12/510:15 pmPDX - SJU
1 stop19h 50mAmerican Airlines
Tue 12/912:49 pmSJU - PDX
1 stop15h 03mAmerican Airlines
Deal found 10/26$429
This Frontier deal was found by Cheapflights users on 10/27. 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.
Tue 11/111:26 pmPDX - SJU
2 stops17h 53mFrontier
Fri 11/142:11 amSJU - PDX
2 stops13h 45mFrontier
Deal found 10/27$445
This American Airlines deal was found by Cheapflights users on 10/25. 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 12/63:15 pmPDX - SJU
2 stops14h 54mAmerican Airlines
Sat 12/136:54 amSJU - PDX
2 stops14h 34mAmerican Airlines
Deal found 10/25$457
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Wed 12/37:18 amPDX - PUJ
1 stop29h 13mMultiple Airlines
Sun 12/76:08 pmPUJ - PDX
2 stops22h 34mMultiple Airlines
Deal found 10/26$509

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 October 28, 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

Mon 3/2

11:59 pm-3:40 pm

1 stop11h 41m

San Juan Luis Munoz Marin Intl

Fri 3/6

8:10 am-7:00 pm

2 stops14h 50m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 1/21

6:00 am-11:59 pm

2 stops13h 59m

San Juan Luis Munoz Marin Intl

Wed 1/28

3:55 pm-10:15 pm

1 stop10h 20m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 1/20

11:05 pm-12:55 pm

1 stop9h 50m

San Juan Luis Munoz Marin Intl

Wed 1/28

2:15 pm-9:49 pm

1 stop11h 34m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 2/19

10:52 pm-2:40 pm

1 stop11h 48m

San Juan Luis Munoz Marin Intl

Tue 2/24

8:35 am-5:51 pm

2 stops13h 16m

$448

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 11/14

7:15 pm-11:35 am

2 stops12h 20m

San Juan Luis Munoz Marin Intl

Fri 11/21

6:40 am-3:05 pm

2 stops12h 25m

$460

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 2/14

10:00 am-12:40 am

2 stops10h 40m

San Juan Luis Munoz Marin Intl

Fri 2/20

6:00 am-2:55 pm

2 stops12h 55m

$466

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 3/3

8:30 am-12:36 am

2 stops12h 06m

San Juan Luis Munoz Marin Intl

Wed 3/4

8:10 am-5:51 pm

2 stops13h 41m

$504

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 1/22

11:05 pm-2:40 pm

1 stop11h 35m

San Juan Luis Munoz Marin Intl

Mon 1/26

2:05 am-1:45 pm

2 stops15h 40m

$509

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 1/19

11:05 pm-12:55 pm

1 stop9h 50m

San Juan Luis Munoz Marin Intl

Tue 1/27

2:05 am-2:48 pm

2 stops16h 43m

$509

PortlandNassau

PDX - NAS

PDXNAS

Portland

Wed 12/10

10:10 pm-1:30 pm

1 stop12h 20m

Nassau Intl

Wed 12/17

2:55 pm-10:19 pm

1 stop10h 24m

$533

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

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 $187). Flying from Portland to Caribbean in December is currently the most expensive (average of $419). 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 October 28, 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 October 28, 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
4,240 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

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
7,994 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

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
9,001 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

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
11,032 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

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
8,116 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

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 United Airlines, Delta, and American Airlines fly from Portland to Caribbean in about 10h 49m. The time it takes to get you to your destination can typically vary by up to 3h 10m. Portland and Caribbean are separated by a distance of 3803 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 $210. Users have also found prices from $213 and $213 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 - Nassau Intl and Portland - Saint Thomas Island Cyril E King.

  • 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 $187). Flying from Portland to Caribbean in December is currently the most expensive (average of $419). 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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$540FlexibilityNo cancel feeOn-time62%
DeltaCheapest$190Average$717FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$248Average$415FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$342Average$713FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$399Average$677FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$431Average$563FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$444Average$725FlexibilityNo cancel feeOn-time63%

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