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Caribbean

$173+ 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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 11, 2025.

Round-trip from

$418
(Frontier)

One-way from

$173
(Booking.com)

Popular in

December

Cheapest in

September

Average price

$453
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 ($42 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 11, 2025.

This Frontier deal was found by Cheapflights users on 9/8. 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.
Sun 11/93:26 pmPDX - SJU
2 stops17h 51mFrontier
Thu 11/132:11 amSJU - PDX
2 stops13h 45mFrontier
Deal found 9/8$393
This Frontier deal was found by Cheapflights users on 9/9. 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 stops19h 16mFrontier
Sun 11/162:11 amSJU - PDX
2 stops13h 45mFrontier
Deal found 9/9$418
This Delta deal was found by Cheapflights users on 9/10. 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 11/910:10 pmPDX - SJU
1 stop10h 36mDelta
Thu 11/133:20 pmSJU - PDX
1 stop10h 45mDelta
Deal found 9/10$419
This Mytrip deal was found by Cheapflights users on 9/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2512:07 pmPDX - SJU
2 stops19h 57mSpirit Airlines
Mon 9/2910:42 amSJU - PDX
2 stops27h 29mSpirit Airlines
Deal found 9/9$430
This Mytrip deal was found by Cheapflights users on 9/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/258:00 amPDX - SJU
3 stops24h 04mMultiple Airlines
Mon 9/2910:42 amSJU - PDX
2 stops27h 29mMultiple Airlines
Deal found 9/9$432
This United Airlines deal was found by Cheapflights users on 9/9. 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 - PUJ
1 stop9h 18mUnited Airlines
Wed 11/1912:56 pmPUJ - PDX
2 stops15h 30mUnited Airlines
Deal found 9/9$436
This United Airlines deal was found by Cheapflights users on 9/9. 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 11/182:05 amSJU - PDX
2 stops15h 42mUnited Airlines
Deal found 9/9$448
This United Airlines deal was found by Cheapflights users on 9/9. 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.
Thu 12/1111:59 pmPDX - PUJ
1 stop12h 03mUnited Airlines
Mon 12/152:05 pmPUJ - PDX
1 stop11h 10mUnited Airlines
Deal found 9/9$451
This United Airlines deal was found by Cheapflights users on 9/10. 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 10/85:00 amPDX - SJU
1 stop9h 30mUnited Airlines
Tue 10/141:05 amSJU - PDX
2 stops14h 37mUnited Airlines
Deal found 9/10$451
This United Airlines deal was found by Cheapflights users on 9/10. 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 11/75:00 amPDX - PUJ
1 stop9h 18mUnited Airlines
Tue 11/1812:56 pmPUJ - PDX
1 stop11h 33mUnited Airlines
Deal found 9/10$456
This American Airlines deal was found by Cheapflights users on 9/11. 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 12/210:15 pmPDX - SJU
1 stop18h 42mAmerican Airlines
Thu 12/117:00 amSJU - PDX
1 stop18h 21mAmerican Airlines
Deal found 9/11$457
This United Airlines deal was found by Cheapflights users on 9/9. 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.
Sat 10/115:15 pmPDX - SJU
2 stops15h 45mUnited Airlines
Sat 10/181:30 pmSJU - PDX
1 stop10h 56mUnited Airlines
Deal found 9/9$462

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 11, 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

Fri 11/14

11:12 pm-2:40 pm

1 stop11h 28m

San Juan Luis Munoz Marin Intl

Tue 11/18

8:10 am-6:36 pm

2 stops14h 26m

$419

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

3:20 pm-11:58 pm

2 stops12h 38m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 10/11

10:32 pm-12:00 pm

1 stop10h 28m

San Juan Luis Munoz Marin Intl

Fri 10/17

1:05 am-11:41 am

2 stops13h 36m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 11/9

5:26 pm-2:10 pm

2 stops16h 44m

San Juan Luis Munoz Marin Intl

Fri 11/14

3:20 pm-10:05 pm

1 stop10h 45m

$419

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Thu 12/11

4:02 pm-12:59 pm

2 stops16h 57m

Punta Cana

Mon 12/15

2:05 pm-9:15 pm

1 stop11h 10m

$451

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Fri 11/7

5:00 am-6:18 pm

1 stop9h 18m

Punta Cana

Tue 11/18

12:56 pm-8:29 pm

1 stop11h 33m

$456

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 12/2

10:15 pm-8:57 pm

1 stop18h 42m

San Juan Luis Munoz Marin Intl

Thu 12/11

7:00 am-9:21 pm

1 stop18h 21m

$457

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 12/3

6:15 am-11:20 pm

2 stops13h 05m

San Juan Luis Munoz Marin Intl

Tue 12/9

8:55 am-7:20 pm

2 stops14h 25m

$457

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 10/17

7:59 pm-2:11 pm

2 stops15h 12m

San Juan Luis Munoz Marin Intl

Wed 11/26

3:20 pm-10:05 pm

1 stop10h 45m

$457

PortlandSantiago de los Caballeros

PDX - STI

PDXSTI

Portland

Sat 1/10

10:55 pm-12:55 pm

1 stop10h 00m

Santiago de los Caballeros

Sat 1/17

4:35 pm-11:29 pm

1 stop10h 54m

$467

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

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 11, 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 11, 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
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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. The time it takes to get you to your destination can typically vary by up to 2h 45m. Portland and Caribbean are separated by a distance of 3447 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 Spirit Airlines. According to our data, you can fly for as low as $173. Users have also found prices from $184 and $191 on Frontier and American Airlines, 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 - Montego Bay Sangster Intl 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, 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 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$540FlexibilityNo cancel feeOn-time62%
DeltaCheapest$212Average$696FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$248Average$415FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$342Average$711FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$396Average$704FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$450Average$729FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$454Average$534FlexibilityNo cancel feeOn-time75%

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