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$178+ 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 5/17. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Apr 9 — Apr 161
Wed 4/9
Wed 4/16
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 April 4, 2025.

Round-trip from

$320
(Booking.com)

One-way from

$178
(Priceline)

Popular in

March

Cheapest in

September

Average price

$515
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. 11% potential increase in price ($75 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($22 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 4, 2025.

This Booking.com deal was found by Cheapflights users on 4/2. 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.
Fri 5/27:01 pmPDX - STT
2 stops13h 23mSpirit Airlines
Fri 5/910:52 amSTT - PDX
2 stops28h 50mSpirit Airlines
Deal found 4/2$320
This Delta deal was found by Cheapflights users on 4/2. 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.
Mon 11/247:00 amPDX - SJU
1 stop12h 50mDelta
Tue 12/27:00 amSJU - PDX
2 stops15h 16mDelta
Deal found 4/2$369
This Mytrip deal was found by Cheapflights users on 4/4. 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.
Tue 5/62:33 pmPDX - SJU
2 stops19h 11mSpirit Airlines
Mon 5/121:33 amSJU - PDX
2 stops38h 09mSpirit Airlines
Deal found 4/4$372
This United Airlines deal was found by Cheapflights users on 4/4. 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.
Tue 5/67:00 amPDX - SJU
2 stops13h 57mUnited Airlines
Tue 5/131:40 pmSJU - PDX
2 stops13h 51mUnited Airlines
Deal found 4/4$388
This American Airlines deal was found by Cheapflights users on 4/3. 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.
Thu 8/281:43 amPDX - SJU
1 stop18h 17mAmerican Airlines
Fri 9/53:42 pmSJU - PDX
1 stop10h 01mAmerican Airlines
Deal found 4/3$417
This Priceline deal was found by Cheapflights users on 4/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/71:37 pmPDX - PUJ
2 stops18h 24mSpirit Airlines
Fri 5/163:22 pmPUJ - PDX
2 stops24h 20mSpirit Airlines
Deal found 4/3$420
This American Airlines deal was found by Cheapflights users on 4/4. 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.
Mon 8/2510:44 pmPDX - AUA
1 stop9h 41mAmerican Airlines
Sat 8/302:40 pmAUA - PDX
1 stop22h 37mAmerican Airlines
Deal found 4/4$446
This United Airlines deal was found by Cheapflights users on 4/2. 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 4/2611:59 pmPDX - NAS
1 stop12h 00mUnited Airlines
Fri 5/212:50 pmNAS - PDX
1 stop11h 43mUnited Airlines
Deal found 4/2$465
This Alaska Airlines deal was found by Cheapflights users on 4/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/159:30 pmPDX - NAS
1 stop19h 29mAlaska Airlines
Sat 5/249:00 amNAS - PDX
2 stops24h 32mAlaska Airlines
Deal found 4/4$467
This CheapOair deal was found by Cheapflights users on 4/3. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/105:40 pmPDX - SJU
2 stops14h 51mMultiple Airlines
Sat 5/174:15 pmSJU - PDX
1 stop27h 58mMultiple Airlines
Deal found 4/3$473
This American Airlines deal was found by Cheapflights users on 4/3. 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.
Thu 5/1510:24 pmPDX - NAS
1 stop17h 51mAmerican Airlines
Tue 5/204:10 pmNAS - PDX
1 stop21h 39mAmerican Airlines
Deal found 4/3$476
This Mytrip deal was found by Cheapflights users on 4/3. 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.
Sat 5/105:40 pmPDX - MBJ
2 stops15h 22mSpirit Airlines
Wed 5/1412:07 pmMBJ - PDX
2 stops30h 38mSpirit Airlines
Deal found 4/3$477

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 April 4, 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

Fri 5/2

7:01 pm-11:24 am

2 stops13h 23m

Saint Thomas Island Cyril E King

Fri 5/9

10:52 am-12:42 pm

2 stops28h 50m

$320

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 5/6

5:15 pm-12:45 pm

2 stops16h 30m

San Juan Luis Munoz Marin Intl

Tue 5/13

1:12 pm-11:15 pm

1 stop13h 03m

$369

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 5/6

2:33 pm-12:44 pm

2 stops19h 11m

San Juan Luis Munoz Marin Intl

Mon 5/12

1:33 am-12:42 pm

2 stops38h 09m

$372

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 5/6

7:00 am-11:57 pm

2 stops13h 57m

San Juan Luis Munoz Marin Intl

Tue 5/13

1:40 pm-12:31 am

2 stops13h 51m

$388

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 8/28

1:43 am-11:00 pm

1 stop18h 17m

San Juan Luis Munoz Marin Intl

Fri 9/5

3:42 pm-10:43 pm

1 stop10h 01m

$417

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Wed 5/7

1:37 pm-11:01 am

2 stops18h 24m

Punta Cana

Fri 5/16

3:22 pm-12:42 pm

2 stops24h 20m

$420

PortlandOranjestad

PDX - AUA

PDXAUA

Portland

Mon 8/25

10:44 pm-11:25 am

1 stop9h 41m

Oranjestad Reina Beatrix

Sat 8/30

2:40 pm-10:17 am

1 stop22h 37m

$446

PortlandNassau

PDX - NAS

PDXNAS

Portland

Sat 4/26

7:35 pm-1:31 pm

2 stops14h 56m

Nassau Intl

Fri 5/2

12:50 pm-9:33 pm

1 stop11h 43m

$465

PortlandNassau

PDX - NAS

PDXNAS

Portland

Thu 5/15

9:30 pm-7:59 pm

1 stop19h 29m

Nassau Intl

Sat 5/24

9:00 am-6:32 am

2 stops24h 32m

$467

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 5/10

5:40 pm-11:31 am

2 stops14h 51m

San Juan Luis Munoz Marin Intl

Sat 5/17

4:15 pm-5:13 pm

1 stop27h 58m

$473

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/3

Showing 1-10 of 53 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 December is currently the most expensive (average of $336). 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 April 4, 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 April 4, 2025.
Alaska Airlines
8.0
Very good
9,836 reviews

Comfort

7.9

Entertainment

7.1

Boarding

8.2

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,836 reviews
Alaska Airlines
8.0
Very good
9,836 reviews

Comfort

7.9

Entertainment

7.1

Boarding

8.2

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,276 reviews
Alaska Airlines
8.0
Very good
9,836 reviews

Comfort

7.9

Entertainment

7.1

Boarding

8.2

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,901 reviews
Alaska Airlines
8.0
Very good
9,836 reviews

Comfort

7.9

Entertainment

7.1

Boarding

8.2

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
LATAM Airlines
7.5
Good
1,752 reviews
Alaska Airlines
8.0
Very good
9,836 reviews

Comfort

7.9

Entertainment

7.1

Boarding

8.2

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,618 reviews
Alaska Airlines
8.0
Very good
9,836 reviews

Comfort

7.9

Entertainment

7.1

Boarding

8.2

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 $178. Users have also found prices from $185 and $191 on American Airlines 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 - 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 December is currently the most expensive (average of $336). 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 9 airlines flying from Portland to Caribbean

Discover the top 9 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 April 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$363FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$242Average$524FlexibilityNo cancel feeOn-time75%
Spirit AirlinesCheapest$245Average$362FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$288Average$392FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$298Average$684FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$327Average$734FlexibilityNo cancel feeOn-time71%
DeltaCheapest$356Average$690FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$450Average$714FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$475Average$717FlexibilityNo cancel feeOn-time83%

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