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$187+ 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 7/13. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
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 junio 12, 2025.

Round-trip from

$333
(FlightHub)

One-way from

$187
(FlightHub)

Popular in

March

Cheapest in

September

Average price

$635
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. 12% potential increase in price ($74 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in June 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 junio 12, 2025.

This FlightHub deal was found by Cheapflights users on 6/12. 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.
mar. 7/812:12 pmPDX - STT
2 stops18h 36mSpirit Airlines
mar. 7/151:25 pmSTT - PDX
2 stops22h 53mSpirit Airlines
Deal found 6/12$333
This FlightHub deal was found by Cheapflights users on 6/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/163:10 pmPDX - SJU
2 stops16h 19mSpirit Airlines
mar. 7/224:43 pmSJU - PDX
2 stops24h 32mSpirit Airlines
Deal found 6/10$378
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/307:19 amPDX - SJU
1 stop13h 32mDelta
jue. 9/412:50 pmSJU - PDX
1 stop12h 22mDelta
Deal found 6/11$399
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 7/44:37 pmPDX - SJU
3 stops39h 02mMultiple Airlines
mié. 7/94:43 pmSJU - PDX
2 stops24h 32mMultiple Airlines
Deal found 6/11$406
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 7/219:22 amPDX - STX
2 stops27h 40mMultiple Airlines
lun. 7/285:09 pmSTX - PDX
3 stops43h 09mMultiple Airlines
Deal found 6/11$425
This United Airlines deal was found by Cheapflights users on 6/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/185:00 amPDX - SJU
1 stop9h 30mUnited Airlines
mié. 8/271:05 amSJU - PDX
1 stop10h 48mUnited Airlines
Deal found 6/11$434
This Frontier deal was found by Cheapflights users on 6/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/186:35 amPDX - SJU
2 stops15h 11mFrontier
jue. 8/287:25 amSJU - PDX
2 stops19h 50mFrontier
Deal found 6/11$439
This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/2210:23 amPDX - STX
2 stops26h 39mSpirit Airlines
lun. 7/285:09 pmSTX - PDX
3 stops43h 09mSpirit Airlines
Deal found 6/10$460
This Southwest deal was found by Cheapflights users on 6/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/106:40 pmPDX - SJU
2 stops12h 35mSouthwest
mar. 9/167:20 amSJU - PDX
2 stops14h 05mSouthwest
Deal found 6/10$467
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/93:10 pmPDX - MBJ
3 stops41h 20mSpirit Airlines
mié. 7/1612:10 pmMBJ - PDX
2 stops23h 08mSpirit Airlines
Deal found 6/11$469
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 7/113:10 pmPDX - PUJ
2 stops21h 45mSpirit Airlines
vie. 7/183:25 pmPUJ - PDX
2 stops25h 50mSpirit Airlines
Deal found 6/11$482
This American Airlines deal was found by Cheapflights users on 6/11. 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.
lun. 8/187:40 amPDX - SJU
2 stops13h 19mAmerican Airlines
jue. 8/282:55 pmSJU - PDX
1 stop21h 29mAmerican Airlines
Deal found 6/11$482

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 junio 12, 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

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

mar. 7/8

12:12 pm-9:48 am

2 stops18h 36m

Saint Thomas Island Cyril E King

mar. 7/15

1:25 pm-9:18 am

2 stops22h 53m

$333

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

mié. 7/16

3:10 pm-10:29 am

2 stops16h 19m

San Juan Luis Munoz Marin Intl

mar. 7/22

4:43 pm-2:15 pm

2 stops24h 32m

$378

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

sáb. 8/30

7:19 am-11:51 pm

1 stop13h 32m

San Juan Luis Munoz Marin Intl

jue. 9/4

12:50 pm-10:12 pm

1 stop12h 22m

$399

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

vie. 7/4

4:37 pm-10:39 am

3 stops39h 02m

San Juan Luis Munoz Marin Intl

mié. 7/9

4:43 pm-2:15 pm

2 stops24h 32m

$406

PortlandChristiansted

PDX - STX

PDXSTX

Portland

lun. 7/21

9:22 am-4:02 pm

2 stops27h 40m

Christiansted Henry Rohlsen

lun. 7/28

5:09 pm-9:18 am

3 stops43h 09m

$425

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

lun. 8/18

5:00 am-5:30 pm

1 stop9h 30m

San Juan Luis Munoz Marin Intl

mié. 8/27

1:05 am-8:53 am

1 stop10h 48m

$434

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

lun. 8/18

6:35 am-12:46 am

2 stops15h 11m

San Juan Luis Munoz Marin Intl

jue. 8/28

7:25 am-12:15 am

2 stops19h 50m

$439

PortlandChristiansted

PDX - STX

PDXSTX

Portland

mar. 7/22

10:23 am-4:02 pm

2 stops26h 39m

Christiansted Henry Rohlsen

lun. 7/28

5:09 pm-9:18 am

3 stops43h 09m

$460

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

mié. 9/10

6:40 pm-10:15 am

2 stops12h 35m

San Juan Luis Munoz Marin Intl

mar. 9/16

7:20 am-6:25 pm

2 stops14h 05m

$467

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

mié. 7/9

3:10 pm-10:30 am

3 stops41h 20m

Montego Bay Sangster Intl

mié. 7/16

12:10 pm-9:18 am

2 stops23h 08m

$469

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

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 junio 12, 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.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 junio 12, 2025.
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Delta
8.0
Very good
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
LATAM Airlines
7.5
Good
1,785 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.

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 $187. Users have also found prices from $190 and $200 on JetBlue 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 - Montego Bay Sangster 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.

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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 8 airlines flying from Portland to Caribbean

Discover the top 8 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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$380FlexibilityNo cancel feeOn-time62%
DeltaCheapest$218Average$709FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$248Average$362FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$306Average$694FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$327Average$720FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$431Average$534FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$450Average$713FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$475Average$737FlexibilityNo cancel feeOn-time83%

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