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Caribbean

$195+ 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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$383
(Frontier)

One-way from

$195
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$481
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. 6% potential increase in price ($40 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 September 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 September 17, 2025.

This Frontier deal was found by Cheapflights users on 9/17. 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 10/1712:43 pmPDX - SJU
2 stops20h 33mFrontier
Fri 10/249:06 pmSJU - PDX
2 stops17h 42mFrontier
Deal found 9/17$383
This Frontier deal was found by Cheapflights users on 9/15. 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 9/15$384
This Frontier deal was found by Cheapflights users on 9/15. 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 10/2812:52 pmPDX - SJU
2 stops19h 27mFrontier
Fri 11/710:39 pmSJU - PDX
2 stops17h 17mFrontier
Deal found 9/15$390
This Frontier deal was found by Cheapflights users on 9/15. 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 10/2412:43 pmPDX - SJU
2 stops20h 33mFrontier
Fri 11/72:11 amSJU - PDX
2 stops13h 45mFrontier
Deal found 9/15$391
This Frontier deal was found by Cheapflights users on 9/16. 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 10/2812:52 pmPDX - SJU
2 stops19h 27mFrontier
Sun 11/22:03 amSJU - PDX
2 stops13h 53mFrontier
Deal found 9/16$406
This United Airlines deal was found by Cheapflights users on 9/15. 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 11/125:00 amPDX - SJU
1 stop9h 25mUnited Airlines
Tue 11/187:45 amSJU - PDX
2 stops14h 51mUnited Airlines
Deal found 9/15$419
This Frontier deal was found by Cheapflights users on 9/15. 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.
Wed 9/247:15 amPDX - SJU
2 stops23h 37mFrontier
Mon 9/299:07 amSJU - PDX
2 stops18h 05mFrontier
Deal found 9/15$425
This Frontier deal was found by Cheapflights users on 9/15. 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 9/278:02 amPDX - SJU
2 stops22h 50mFrontier
Mon 9/299:07 amSJU - PDX
2 stops18h 05mFrontier
Deal found 9/15$428
This United Airlines deal was found by Cheapflights users on 9/17. 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 10/176:25 pmPDX - SJU
2 stops15h 09mUnited Airlines
Thu 10/231:05 amSJU - PDX
1 stop10h 48mUnited Airlines
Deal found 9/17$448
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Mon 10/1310:17 pmPDX - SJU
1 stop10h 43mUnited Airlines
Thu 10/161:05 amSJU - PDX
1 stop10h 48mUnited Airlines
Deal found 9/16$449
This Southwest deal was found by Cheapflights users on 9/15. 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 11/126:15 amPDX - SJU
2 stops13h 05mSouthwest
Tue 11/188:55 amSJU - PDX
2 stops13h 20mSouthwest
Deal found 9/15$450
This United Airlines deal was found by Cheapflights users on 9/16. 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 10/315:00 amPDX - PUJ
1 stop9h 18mUnited Airlines
Fri 11/72:55 pmPUJ - PDX
1 stop11h 38mUnited Airlines
Deal found 9/16$455

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 September 17, 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

Tue 1/20

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

$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

Sat 1/10

10:55 pm-9:24 pm

1 stop18h 29m

Santiago de los Caballeros

Sat 1/17

7:00 am-7:32 pm

2 stops16h 32m

$472

PortlandSantiago de los Caballeros

PDX - STI

PDXSTI

Portland

Sun 11/23

12:35 am-12:59 am

2 stops20h 24m

Santiago de los Caballeros

Mon 12/8

6:35 am-8:45 pm

1 stop18h 10m

$472

PortlandSantiago de los Caballeros

PDX - STI

PDXSTI

Portland

Mon 11/24

12:35 am-12:59 am

2 stops20h 24m

Santiago de los Caballeros

Tue 12/9

6:35 am-8:45 pm

1 stop18h 10m

$472

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 1/8

5:45 pm-2:16 pm

2 stops16h 31m

San Juan Luis Munoz Marin Intl

Sat 1/17

6:15 am-7:08 pm

2 stops16h 53m

$482

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 11/8

12:35 am-5:20 pm

2 stops12h 45m

San Juan Luis Munoz Marin Intl

Thu 11/13

2:10 pm-11:56 pm

2 stops13h 46m

$482

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 1/5

5:45 pm-2:16 pm

2 stops16h 31m

San Juan Luis Munoz Marin Intl

Thu 1/15

7:30 am-8:47 pm

2 stops17h 17m

$482

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 11/7

5:25 pm-3:11 pm

2 stops17h 46m

San Juan Luis Munoz Marin Intl

Fri 11/14

3:20 pm-10:05 pm

1 stop10h 45m

$482

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Mon 10/6

1:40 pm-12:28 pm

1 stop19h 48m

Punta Cana

Thu 10/16

2:09 pm-9:48 pm

1 stop10h 39m

$487

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

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, September is the cheapest month in which you can book a flight from Portland to Caribbean (average of $254). Flying from Portland to Caribbean 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 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 September 17, 2025.

When flying from Portland to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 17, 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

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

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
8.0
Very good
7,961 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

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
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

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
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

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
8,023 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

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 Delta, American Airlines, and United Airlines fly from Portland to Caribbean in about 10h 25m. The time it takes to get you to your destination can typically vary by up to 9h 04m. 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 $210. Users have also found prices from $210 and $274 on Delta and Southwest, 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 - Punta Cana.

  • 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, September is the cheapest month in which you can book a flight from Portland to Caribbean (average of $254). Flying from Portland to Caribbean 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

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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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$540FlexibilityNo cancel feeOn-time62%
DeltaCheapest$190Average$698FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$248Average$415FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$341Average$700FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$399Average$704FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$450Average$729FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$454Average$534FlexibilityNo cancel feeOn-time75%

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