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$111+ 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 4/1. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Feb 28 — Mar 71
Fri 2/28
Fri 3/7
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 February 23, 2025.

Round-trip from

$246
(Booking.com)

One-way from

$112
(Trip.com)

Popular in

March

Cheapest in

September

Average price

$562
From Oregon to Caribbean
Search Deals
One-way flight from Oregon to Caribbean
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($71 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 February 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 February 23, 2025.

This Booking.com deal was found by Cheapflights users on 2/22. 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.
Tue 4/86:13 pmPDX - STT
2 stops15h 40mSpirit Airlines
Tue 4/1510:45 amSTT - PDX
2 stops24h 37mSpirit Airlines
Deal found 2/22$246
This Booking.com deal was found by Cheapflights users on 2/22. 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.
Mon 4/71:31 pmBOI - SJU
2 stops25h 03mSpirit Airlines
Tue 4/158:55 pmSJU - BOI
2 stops18h 44mSpirit Airlines
Deal found 2/22$275
This Frontier deal was found by Cheapflights users on 2/22. 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.
Mon 5/51:15 pmPDX - PUJ
2 stops19h 30mFrontier
Sun 5/111:10 pmPUJ - PDX
2 stops22h 43mFrontier
Deal found 2/22$321
This CheapOair deal was found by Cheapflights users on 2/22. 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.
Sun 3/97:32 pmPDX - SJU
2 stops23h 18mSpirit Airlines
Wed 3/1212:05 pmSJU - PDX
2 stops28h 33mSpirit Airlines
Deal found 2/22$333
This FlightHub deal was found by Cheapflights users on 2/22. 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.
Mon 5/511:02 amPDX - PUJ
2 stops21h 42mSpirit Airlines
Mon 5/121:50 pmPUJ - PDX
2 stops21h 22mSpirit Airlines
Deal found 2/22$352
This American Airlines deal was found by Cheapflights users on 2/22. 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.
Tue 4/15:57 pmPDX - SJU
2 stops13h 58mAmerican Airlines
Wed 4/96:21 amSJU - PDX
1 stop20h 07mAmerican Airlines
Deal found 2/22$369
This Priceline deal was found by Cheapflights users on 2/22. 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.
Mon 3/177:32 pmPDX - AUA
2 stops16h 13mSpirit Airlines
Tue 3/253:50 pmAUA - PDX
2 stops21h 30mSpirit Airlines
Deal found 2/22$379
This FlightHub deal was found by Cheapflights users on 2/22. 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.
Sat 5/311:02 amPDX - MBJ
2 stops21h 53mSpirit Airlines
Sat 5/1012:11 pmMBJ - PDX
2 stops22h 01mSpirit Airlines
Deal found 2/22$393
This Expedia deal was found by Cheapflights users on 2/22. 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.
Mon 4/71:23 pmBOI - SJU
1 stop13h 37mMultiple Airlines
Tue 4/158:55 pmSJU - BOI
2 stops18h 44mMultiple Airlines
Deal found 2/22$403
This Delta deal was found by Cheapflights users on 2/22. 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.
Sun 3/237:15 pmBOI - SJU
2 stops18h 02mDelta
Sat 3/297:45 amSJU - BOI
2 stops17h 11mDelta
Deal found 2/22$405
This CheapOair deal was found by Cheapflights users on 2/22. 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 5/1011:10 amPDX - SJU
2 stops19h 46mMultiple Airlines
Sat 5/174:15 pmSJU - PDX
1 stop28h 16mMultiple Airlines
Deal found 2/22$420
This United Airlines deal was found by Cheapflights users on 2/22. 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.
Wed 4/97:30 pmPDX - NAS
2 stops16h 29mUnited Airlines
Wed 4/164:01 pmNAS - PDX
1 stop9h 35mUnited Airlines
Deal found 2/22$435

Find flights from Oregon to Caribbean within your budget

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 February 23, 2025.

Fly from

Oregon

Fly to

Caribbean

Route

Depart

Return

Price

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Tue 4/8

6:13 pm-12:53 pm

2 stops15h 40m

Saint Thomas Island Cyril E King

Tue 4/15

10:45 am-8:22 am

2 stops24h 37m

$246

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Mon 4/7

1:31 pm-4:34 pm

2 stops25h 03m

San Juan Luis Munoz Marin Intl

Tue 4/15

8:55 pm-1:39 pm

2 stops18h 44m

$275

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Mon 5/5

1:15 pm-11:45 am

2 stops19h 30m

Punta Cana

Sun 5/11

1:10 pm-8:53 am

2 stops22h 43m

$321

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 3/9

7:32 pm-9:50 pm

2 stops23h 18m

San Juan Luis Munoz Marin Intl

Wed 3/12

12:05 pm-1:38 pm

2 stops28h 33m

$333

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Mon 5/5

11:02 am-11:44 am

2 stops21h 42m

Punta Cana

Mon 5/12

1:50 pm-8:12 am

2 stops21h 22m

$352

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 4/1

5:57 pm-10:55 am

2 stops13h 58m

San Juan Luis Munoz Marin Intl

Wed 4/9

6:21 am-11:28 pm

1 stop20h 07m

$369

PortlandOranjestad

PDX - AUA

PDXAUA

Portland

Mon 3/17

7:32 pm-2:45 pm

2 stops16h 13m

Oranjestad Reina Beatrix

Tue 3/25

3:50 pm-10:20 am

2 stops21h 30m

$379

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Sat 5/3

11:02 am-10:55 am

2 stops21h 53m

Montego Bay Sangster Intl

Sat 5/10

12:11 pm-8:12 am

2 stops22h 01m

$393

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Mon 4/7

1:23 pm-5:00 am

1 stop13h 37m

San Juan Luis Munoz Marin Intl

Tue 4/15

8:55 pm-1:39 pm

2 stops18h 44m

$403

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Sun 3/23

7:15 pm-3:17 pm

2 stops18h 02m

San Juan Luis Munoz Marin Intl

Sat 3/29

7:45 am-10:56 pm

2 stops17h 11m

$405

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

Showing 1-10 of 47 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.

Travel insights for flights from Oregon to Caribbean

Get recent, data-driven insights about flights from Oregon to Caribbean including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $363). 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 February 23, 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 February 23, 2025.
Southwest
8.1
Very good
4,395 reviews

Food

7.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Overall

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,395 reviews
Southwest
8.1
Very good
4,395 reviews

Food

7.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Overall

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,706 reviews
Southwest
8.1
Very good
4,395 reviews

Food

7.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Overall

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,203 reviews
Southwest
8.1
Very good
4,395 reviews

Food

7.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Overall

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,754 reviews
Southwest
8.1
Very good
4,395 reviews

Food

7.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Overall

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,395 reviews

Food

7.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Overall

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $127. Users have also found prices from $165 and $209 on American Airlines and United 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 March is currently the most expensive (average of $363). 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 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 February 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$352FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$213Average$372FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$242Average$1,714FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$281Average$721FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$288Average$509FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$328Average$729FlexibilityNo cancel feeOn-time71%
DeltaCheapest$354Average$724FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$425Average$656FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$475Average$717FlexibilityNo cancel feeOn-time83%
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