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$155+ 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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
jul. 21 — jul. 281
lun. 7/21
lun. 7/28
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 julio 16, 2025.

Round-trip from

$338
(FlightHub)

One-way from

$155
(Mytrip)

Popular in

December

Cheapest in

October

Average price

$580
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 ($19 potential savings vs. average RT price).
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Average for round-trip flights in July 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 julio 16, 2025.

This FlightHub deal was found by Cheapflights users on 7/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/242:35 pmPDX - SJU
2 stops23h 11mSpirit Airlines
jue. 10/301:10 amSJU - PDX
2 stops15h 20mSpirit Airlines
Deal found 7/14$338
This Mytrip deal was found by Cheapflights users on 7/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/298:46 amPDX - SJU
3 stops27h 24mMultiple Airlines
jue. 9/1112:06 pmSJU - PDX
3 stops26h 06mMultiple Airlines
Deal found 7/16$367
This Frontier deal was found by Cheapflights users on 7/16. 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.
vie. 8/151:40 pmPDX - SJU
2 stops21h 38mFrontier
jue. 8/2112:59 amSJU - PDX
2 stops20h 15mFrontier
Deal found 7/16$377
This American Airlines deal was found by Cheapflights users on 7/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/169:56 pmPDX - SJU
1 stop14h 56mAmerican Airlines
mié. 10/11:37 pmSJU - PDX
2 stops13h 28mAmerican Airlines
Deal found 7/16$399
This Delta deal was found by Cheapflights users on 7/14. 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.
dom. 11/167:00 amPDX - SJU
1 stop12h 50mDelta
jue. 12/41:50 pmSJU - PDX
1 stop12h 42mDelta
Deal found 7/14$409
This FlightHub deal was found by Cheapflights users on 7/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/23:10 pmPDX - STT
2 stops15h 38mSpirit Airlines
dom. 8/101:25 pmSTT - PDX
2 stops22h 53mSpirit Airlines
Deal found 7/15$433
This Mytrip deal was found by Cheapflights users on 7/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/712:07 pmPDX - PUJ
3 stops23h 07mSpirit Airlines
jue. 9/113:19 pmPUJ - PDX
3 stops30h 45mSpirit Airlines
Deal found 7/16$477
This Booking.com deal was found by Cheapflights users on 7/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/52:35 pmPDX - PUJ
2 stops17h 35mMultiple Airlines
mar. 11/1110:25 pmPUJ - PDX
2 stops24h 05mMultiple Airlines
Deal found 7/14$481
This Delta deal was found by Cheapflights users on 7/13. 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.
mar. 8/1210:05 pmPDX - NAS
1 stop10h 43mDelta
mar. 8/193:05 pmNAS - PDX
1 stop10h 07mDelta
Deal found 7/13$489
This United Airlines deal was found by Cheapflights users on 7/15. 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.
mar. 9/210:45 pmPDX - PUJ
1 stop12h 20mUnited Airlines
lun. 9/84:35 pmPUJ - PDX
2 stops19h 53mUnited Airlines
Deal found 7/15$491
This American Airlines deal was found by Cheapflights users on 7/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/1111:58 pmPDX - PUJ
1 stop11h 07mAmerican Airlines
vie. 10/174:23 pmPUJ - PDX
1 stop23h 38mAmerican Airlines
Deal found 7/16$497
This Expedia deal was found by Cheapflights users on 7/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/119:50 amPDX - NAS
2 stops24h 05mAir Canada
mié. 11/191:50 pmNAS - PDX
2 stops27h 55mAir Canada
Deal found 7/15$502

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 julio 16, 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

vie. 10/24

2:35 pm-4:46 pm

2 stops23h 11m

San Juan Luis Munoz Marin Intl

jue. 10/30

1:10 am-1:30 pm

2 stops15h 20m

$338

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

vie. 8/29

8:46 am-3:10 pm

3 stops27h 24m

San Juan Luis Munoz Marin Intl

jue. 9/11

12:06 pm-11:12 am

3 stops26h 06m

$367

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

vie. 8/15

1:40 pm-2:18 pm

2 stops21h 38m

San Juan Luis Munoz Marin Intl

jue. 8/21

12:59 am-6:14 pm

2 stops20h 15m

$377

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

dom. 1/11

5:45 pm-2:16 pm

2 stops16h 31m

San Juan Luis Munoz Marin Intl

jue. 1/22

2:12 pm-11:33 pm

1 stop13h 21m

$399

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

mar. 12/2

11:13 pm-5:10 pm

1 stop13h 57m

San Juan Luis Munoz Marin Intl

jue. 12/11

12:50 pm-11:16 pm

1 stop14h 26m

$419

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

sáb. 8/2

3:10 pm-9:48 am

2 stops15h 38m

Saint Thomas Island Cyril E King

dom. 8/10

1:25 pm-9:18 am

2 stops22h 53m

$433

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

dom. 9/7

12:07 pm-2:14 pm

3 stops23h 07m

Punta Cana

jue. 9/11

3:19 pm-7:04 pm

3 stops30h 45m

$477

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

mié. 11/5

2:35 pm-12:10 pm

2 stops17h 35m

Punta Cana

mar. 11/11

10:25 pm-6:30 pm

2 stops24h 05m

$481

PortlandNassau

PDX - NAS

PDXNAS

Portland

mar. 8/12

10:05 pm-11:48 am

1 stop10h 43m

Nassau Intl

mar. 8/19

3:05 pm-10:12 pm

1 stop10h 07m

$489

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

mar. 9/2

10:45 pm-2:05 pm

1 stop12h 20m

Punta Cana

lun. 9/8

4:35 pm-9:28 am

2 stops19h 53m

$491

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/14

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 julio 16, 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 julio 16, 2025.
Read through reviews of airlines operating flights from Portland to Caribbean, such as Alaska Airlines, Southwest, and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

EUG - SEA

Mobility support was fabulous No flight entertainment that I was aware of.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

EUG - SEA

Mobility support was fabulous No flight entertainment that I was aware of.
Southwest
8.0
Very good
4,241 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

EUG - SEA

Mobility support was fabulous No flight entertainment that I was aware of.
Delta
8.0
Very good
7,957 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

EUG - SEA

Mobility support was fabulous No flight entertainment that I was aware of.
United Airlines
7.4
Good
8,863 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

EUG - SEA

Mobility support was fabulous No flight entertainment that I was aware of.
JetBlue
7.3
Good
2,909 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

EUG - SEA

Mobility support was fabulous No flight entertainment that I was aware of.

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.

  • 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 $155. Users have also found prices from $200 and $203 on Delta 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 - Punta Cana and Portland - Montego Bay Sangster 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 julio 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$369FlexibilityNo cancel feeOn-time62%
DeltaCheapest$216Average$718FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$248Average$351FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$314Average$693FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$328Average$719FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$450Average$729FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$454Average$549FlexibilityNo cancel feeOn-time75%

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