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$144+ Cheap flights from Oregon 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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
abr. 22 — abr. 291
mar. 4/22
mar. 4/29
1 adult, Economy
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Cheap flight deals from Oregon to Caribbean

Keep the following information in mind while searching for Oregon to Caribbean flight deals. Data was last updated abril 17, 2025.

Round-trip from

$369
(Delta)

One-way from

$144
(Cheapflightsfares)

Popular in

March

Cheapest in

September

Average price

$515
From Oregon to Caribbean
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One-way flight from Oregon to Caribbean
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Highest demand for flights based on searches. 12% potential increase in price ($79 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 April 2025
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Find flight deals from Oregon to Caribbean

Cheapest flights from Oregon to Caribbean
Explore the most affordable flight options available from Oregon to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on abril 17, 2025.

This Delta deal was found by Cheapflights users on 4/17. 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. 9/167:55 pmPDX - SJU
2 stops13h 08mDelta
mié. 10/11:13 pmSJU - PDX
1 stop13h 16mDelta
Deal found 4/17$369
This Booking.com deal was found by Cheapflights users on 4/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/165:40 pmPDX - STT
2 stops18h 14mSpirit Airlines
vie. 5/2310:52 amSTT - PDX
2 stops28h 50mSpirit Airlines
Deal found 4/16$375
This American Airlines deal was found by Cheapflights users on 4/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/65:18 pmBOI - SJU
2 stops15h 57mAmerican Airlines
sáb. 9/135:25 pmSJU - BOI
2 stops21h 09mAmerican Airlines
Deal found 4/15$405
This Mytrip deal was found by Cheapflights users on 4/17. 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. 5/37:01 pmPDX - SJU
2 stops24h 31mSpirit Airlines
vie. 5/161:33 amSJU - PDX
3 stops18h 12mSpirit Airlines
Deal found 4/17$409
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/317:30 pmBOI - SJU
2 stops15h 40mDelta
sáb. 11/81:50 pmSJU - BOI
2 stops13h 27mDelta
Deal found 4/16$415
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/27:55 pmPDX - AUA
2 stops15h 15mDelta
vie. 9/193:25 pmAUA - PDX
2 stops20h 39mDelta
Deal found 4/16$416
This American Airlines deal was found by Cheapflights users on 4/17. 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. 8/2510:44 pmPDX - AUA
1 stop9h 41mAmerican Airlines
sáb. 8/302:40 pmAUA - PDX
1 stop9h 08mAmerican Airlines
Deal found 4/17$436
This CheapOair deal was found by Cheapflights users on 4/17. 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.
sáb. 5/101:37 pmPDX - SJU
2 stops18h 54mMultiple Airlines
sáb. 5/174:15 pmSJU - PDX
1 stop25h 39mMultiple Airlines
Deal found 4/17$437
This FlightHub deal was found by Cheapflights users on 4/17. 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. 6/75:40 pmPDX - PUJ
2 stops17h 37mSpirit Airlines
mié. 6/113:22 pmPUJ - PDX
2 stops22h 55mSpirit Airlines
Deal found 4/17$449
This American Airlines deal was found by Cheapflights users on 4/17. 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. 5/196:07 pmPDX - SJU
2 stops13h 52mAmerican Airlines
lun. 6/26:10 amSJU - PDX
1 stop19h 57mAmerican Airlines
Deal found 4/17$452
This United Airlines deal was found by Cheapflights users on 4/17. 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. 9/165:40 pmPDX - SJU
2 stops17h 05mUnited Airlines
mar. 9/301:05 amSJU - PDX
2 stops14h 38mUnited Airlines
Deal found 4/17$459
This American Airlines deal was found by Cheapflights users on 4/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/611:59 pmPDX - NAS
1 stop12h 01mAmerican Airlines
sáb. 5/1010:20 amNAS - PDX
1 stop15h 47mAmerican Airlines
Deal found 4/15$465

Cheapflights Fare Finder

Customize your flight search to find flights from Oregon 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 abril 17, 2025.
Use the filters below to find and compare flights from Oregon to Caribbean that are best for you.

Fly from

Oregon

Fly to

Caribbean

Route

Depart

Return

Price

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

mar. 9/16

7:55 pm-12:03 pm

2 stops13h 08m

San Juan Luis Munoz Marin Intl

mié. 10/1

1:13 pm-11:29 pm

1 stop13h 16m

$369

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

vie. 5/16

5:40 pm-2:54 pm

2 stops18h 14m

Saint Thomas Island Cyril E King

vie. 5/23

10:52 am-12:42 pm

2 stops28h 50m

$375

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

sáb. 9/6

5:18 pm-12:45 pm

2 stops17h 27m

San Juan Luis Munoz Marin Intl

sáb. 9/13

3:58 pm-12:34 pm

2 stops22h 36m

$405

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

sáb. 5/3

7:01 pm-10:32 pm

2 stops24h 31m

San Juan Luis Munoz Marin Intl

vie. 5/16

1:33 am-4:45 pm

3 stops18h 12m

$409

PortlandOranjestad

PDX - AUA

PDXAUA

Portland

mar. 9/2

7:55 pm-2:10 pm

2 stops15h 15m

Oranjestad Reina Beatrix

vie. 9/19

3:25 pm-9:04 am

2 stops20h 39m

$416

PortlandOranjestad

PDX - AUA

PDXAUA

Portland

lun. 8/25

10:44 pm-11:25 am

1 stop9h 41m

Oranjestad Reina Beatrix

sáb. 8/30

2:40 pm-8:48 pm

1 stop9h 08m

$436

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

sáb. 5/10

1:37 pm-11:31 am

2 stops18h 54m

San Juan Luis Munoz Marin Intl

sáb. 5/17

4:15 pm-2:54 pm

1 stop25h 39m

$437

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

sáb. 6/7

5:40 pm-2:17 pm

2 stops17h 37m

Punta Cana

mié. 6/11

3:22 pm-11:17 am

2 stops22h 55m

$449

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

lun. 5/19

6:07 pm-10:59 am

2 stops13h 52m

San Juan Luis Munoz Marin Intl

lun. 6/2

6:10 am-11:07 pm

1 stop19h 57m

$452

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

mar. 9/16

11:59 pm-2:44 pm

1 stop11h 45m

San Juan Luis Munoz Marin Intl

mar. 9/30

1:05 am-8:53 am

1 stop10h 48m

$459

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

Showing 1-10 of 60 results
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Best time to book a flight from Oregon to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Oregon 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 Oregon to Caribbean

What is the cheapest month to book a flight from Oregon to Caribbean?

Currently, September is the cheapest month in which you can book a flight from Oregon to Caribbean (average of $254). Flying from Oregon 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 OR to CB?

Find hourly flight availability from Oregon 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 abril 17, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oregon to Caribbean as you normally would.

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 abril 17, 2025.
Alaska Airlines
8.0
Very good
9,882 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,882 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,280 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,917 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
LATAM Airlines
7.5
Good
1,761 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,667 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Related info for your journey

Find useful and relevant information for your journey from Oregon to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Oregon to Caribbean one-way?

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $144. Users have also found prices from $180 and $185 on JetBlue and American Airlines, respectively.

  • Can I find deals for flights from Oregon to Caribbean that include hotel bookings?

    Yes. In addition to deals on Oregon to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oregon to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oregon to Caribbean.

  • Can I find deals for business class flights from Oregon to Caribbean?

    Yes. Cheapflights offers flight deals from Oregon 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 Oregon to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from Oregon to Caribbean (average of $254). Flying from Oregon 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Oregon 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 Oregon to Caribbean

Discover the top 9 airlines that operate flights from Oregon 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 abril 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$306FlexibilityNo cancel feeOn-time62%
DeltaCheapest$202Average$735FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$242Average$591FlexibilityNo cancel feeOn-time75%
Spirit AirlinesCheapest$245Average$363FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$288Average$382FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$298Average$720FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$327Average$736FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$450Average$702FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$475Average$717FlexibilityNo cancel feeOn-time83%

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