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$189+ 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
ago. 3 — ago. 101
dom. 8/3
dom. 8/10
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 29, 2025.

Round-trip from

$389
(Southwest)

One-way from

$189
(Mytrip)

Popular in

March

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. 8% potential increase in price ($53 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 29, 2025.

This Southwest deal was found by Cheapflights users on 7/29. 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.
mar. 9/96:00 amPDX - SJU
2 stops13h 30mSouthwest
vie. 9/195:50 amSJU - PDX
1 stop13h 10mSouthwest
Deal found 7/29$389
This Delta deal was found by Cheapflights users on 7/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/287:15 amPDX - SJU
1 stop13h 32mDelta
sáb. 10/42:26 pmSJU - PDX
1 stop10h 21mDelta
Deal found 7/27$399
This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/2512:07 pmPDX - SJU
3 stops33h 37mSpirit Airlines
dom. 9/282:48 pmSJU - PDX
2 stops31h 16mSpirit Airlines
Deal found 7/28$403
This American Airlines deal was found by Cheapflights users on 7/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/610:45 pmPDX - SJU
1 stop10h 56mAmerican Airlines
jue. 11/136:44 amSJU - PDX
2 stops14h 28mAmerican Airlines
Deal found 7/28$419
This Frontier deal was found by Cheapflights users on 7/28. 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.
sáb. 8/27:01 pmPDX - SJU
2 stops17h 51mFrontier
mié. 8/139:30 amSJU - PDX
2 stops16h 54mFrontier
Deal found 7/28$440
This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/208:04 pmPDX - SJU
2 stops15h 57mMultiple Airlines
sáb. 9/273:19 pmSJU - PDX
3 stops28h 15mMultiple Airlines
Deal found 7/28$476
This American Airlines deal was found by Cheapflights users on 7/27. 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 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. 10/173:21 pmPUJ - PDX
1 stop21h 10mAmerican Airlines
Deal found 7/27$487
This American Airlines deal was found by Cheapflights users on 7/26. 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.
vie. 12/56:44 pmPDX - STX
2 stops16h 11mAmerican Airlines
sáb. 12/134:35 pmSTX - PDX
1 stop10h 41mAmerican Airlines
Deal found 7/26$489
This American Airlines deal was found by Cheapflights users on 7/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/189:52 pmPDX - NAS
1 stop9h 08mAmerican Airlines
mar. 10/2111:40 amNAS - PDX
1 stop11h 34mAmerican Airlines
Deal found 7/28$489
This United Airlines deal was found by Cheapflights users on 7/29. 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. 9/1610:50 pmPDX - SJU
1 stop11h 55mUnited Airlines
mar. 9/301:05 amSJU - PDX
1 stop10h 48mUnited Airlines
Deal found 7/29$489
This Delta deal was found by Cheapflights users on 7/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/91:30 pmPDX - PUJ
1 stop19h 55mDelta
mar. 9/163:59 pmPUJ - PDX
2 stops19h 56mDelta
Deal found 7/26$491
This FlightHub deal was found by Cheapflights users on 7/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/277:52 pmPDX - STT
2 stops40h 27mSpirit Airlines
lun. 9/810:49 amSTT - PDX
2 stops27h 23mSpirit Airlines
Deal found 7/27$491

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 29, 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

mar. 9/9

6:00 am-10:30 pm

2 stops13h 30m

San Juan Luis Munoz Marin Intl

vie. 9/19

5:50 am-4:00 pm

1 stop13h 10m

$389

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

mar. 1/20

12:55 am-3:20 pm

1 stop10h 25m

San Juan Luis Munoz Marin Intl

mié. 1/28

7:00 am-7:11 pm

2 stops16h 11m

$399

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

jue. 9/25

12:07 pm-12:44 am

3 stops33h 37m

San Juan Luis Munoz Marin Intl

dom. 9/28

2:48 pm-7:04 pm

2 stops31h 16m

$403

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

jue. 11/6

10:45 pm-1:41 pm

1 stop10h 56m

San Juan Luis Munoz Marin Intl

jue. 11/13

6:44 am-5:12 pm

2 stops14h 28m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

sáb. 9/20

8:04 pm-3:01 pm

2 stops15h 57m

San Juan Luis Munoz Marin Intl

sáb. 9/27

3:19 pm-4:34 pm

3 stops28h 15m

$476

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

sáb. 10/11

11:58 pm-2:05 pm

1 stop11h 07m

Punta Cana

vie. 10/17

3:21 pm-9:31 am

1 stop21h 10m

$487

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

mar. 9/16

10:50 pm-1:45 pm

1 stop11h 55m

San Juan Luis Munoz Marin Intl

mar. 9/23

1:25 pm-9:37 pm

1 stop11h 12m

$489

PortlandChristiansted

PDX - STX

PDXSTX

Portland

vie. 12/5

6:44 pm-2:55 pm

2 stops16h 11m

Christiansted Henry Rohlsen

sáb. 12/13

4:35 pm-11:16 pm

1 stop10h 41m

$489

PortlandNassau

PDX - NAS

PDXNAS

Portland

sáb. 10/18

9:52 pm-10:00 am

1 stop9h 08m

Nassau Intl

mar. 10/21

11:40 am-8:14 pm

1 stop11h 34m

$489

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

mar. 9/9

1:36 pm-12:25 pm

2 stops19h 49m

Punta Cana

mar. 9/16

3:59 pm-8:55 am

2 stops19h 56m

$491

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 54 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 29, 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 29, 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

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,238 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,977 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,899 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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 $189. Users have also found prices from $200 and $243 on American Airlines and Air Canada, 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 julio 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$369FlexibilityNo cancel feeOn-time62%
DeltaCheapest$212Average$703FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$248Average$379FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$318Average$691FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$328Average$723FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$450Average$728FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$454Average$549FlexibilityNo cancel feeOn-time75%

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