Caribbean Islands

$158+ Cheap flights from Oregon to Caribbean Islands

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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Dec 28 — Jan 41
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Oregon to Caribbean Islands with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Oregon to Caribbean Islands

Discover tips and strategies to find the most affordable flight options for your journey from Oregon (USOR) to Caribbean Islands (zzEPX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 23, 2024.

Round-trip from

$323
(FlightHub)

One-way from

$158
(CheapOair)
From Oregon to Caribbean Islands
One-way flight from Oregon to Caribbean Islands

Find flight deals from Oregon to Caribbean Islands

Cheapest flights from Oregon to Caribbean Islands
Explore the most affordable flight options available from Oregon to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 23, 2024.

This American Airlines deal was found by Cheapflights users on 12/21. 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.
Sat 12/2810:42 pmPDX - SJU
1 stop10h 53mAmerican Airlines
Tue 12/317:05 amSJU - PDX
1 stop20h 33mAmerican Airlines
Deal found 12/21$574
This American Airlines deal was found by Cheapflights users on 12/22. 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.
Mon 12/2310:42 pmPDX - NAS
1 stop16h 30mAmerican Airlines
Thu 12/263:10 pmNAS - PDX
1 stop12h 45mAmerican Airlines
Deal found 12/22$603
This FlightHub deal was found by Cheapflights users on 12/21. 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.
Thu 12/2611:57 amBOI - SJU
2 stops24h 22mSpirit Airlines
Mon 3/36:00 amSJU - BOI
2 stops39h 46mSpirit Airlines
Deal found 12/21$719
This Mytrip deal was found by Cheapflights users on 12/21. 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.
Fri 12/2711:59 pmPDX - SJU
3 stops35h 20mMultiple Airlines
Tue 1/76:35 pmSJU - PDX
2 stops23h 14mMultiple Airlines
Deal found 12/21$766
This FlightHub deal was found by Cheapflights users on 12/22. 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.
Sun 12/297:19 pmPDX - SJU
2 stops18h 21mSpirit Airlines
Sun 1/52:45 amSJU - PDX
2 stops44h 08mSpirit Airlines
Deal found 12/22$784
This Delta deal was found by Cheapflights users on 12/22. 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.
Mon 12/235:10 pmPDX - NAS
2 stops15h 31mDelta
Thu 12/261:34 pmNAS - PDX
2 stops13h 22mDelta
Deal found 12/22$793
This Delta deal was found by Cheapflights users on 12/21. 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.
Thu 12/265:10 pmBOI - SJU
2 stops15h 25mDelta
Mon 3/34:10 pmSJU - BOI
1 stop10h 48mDelta
Deal found 12/21$794
This deal was found by Cheapflights users on 12/22. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2511:59 pmPDX - NAS
1 stop10h 34mUnited Airlines
Tue 12/3112:55 pmNAS - PDX
1 stop10h 50mUnited Airlines
Deal found 12/22$858
This Booking.com deal was found by Cheapflights users on 12/22. 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 12/236:44 pmPDX - PUJ
1 stop16h 17mSun Country Air
Mon 12/304:05 pmPUJ - PDX
1 stop21h 16mSun Country Air
Deal found 12/22$860
This American Airlines deal was found by Cheapflights users on 12/22. 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.
Mon 12/2310:42 pmPDX - STT
1 stop9h 58mAmerican Airlines
Mon 12/304:10 pmSTT - PDX
1 stop11h 28mAmerican Airlines
Deal found 12/22$865
This Southwest deal was found by Cheapflights users on 12/21. 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.
Wed 12/251:10 pmPDX - SJU
2 stops17h 15mSouthwest
Tue 12/3111:45 amSJU - PDX
2 stops14h 50mSouthwest
Deal found 12/21$879
This Southwest deal was found by Cheapflights users on 12/20. 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.
Sat 12/216:25 pmPDX - PLS
2 stops17h 35mSouthwest
Sat 12/283:20 pmPLS - PDX
2 stops20h 05mSouthwest
Deal found 12/20$883

Find flights from Oregon to Caribbean Islands within your budget

Customize your flight search to find flights from Oregon to Caribbean Islands 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 December 23, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Thu 1/30

5:30 pm-1:48 pm

2 stops16h 18m

Saint Thomas Island Cyril E King

Sun 2/9

11:51 am-9:21 am

2 stops25h 30m

$323

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 2/18

10:16 am-5:01 pm

2 stops26h 45m

San Juan Luis Munoz Marin Intl

Sun 2/23

5:56 pm-9:21 am

2 stops19h 25m

$381

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 2/23

10:55 pm-12:15 pm

1 stop9h 20m

San Juan Luis Munoz Marin Intl

Mon 3/3

7:45 am-11:58 pm

1 stop20h 13m

$386

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Sun 1/5

11:57 am-5:40 pm

2 stops26h 43m

San Juan Luis Munoz Marin Intl

Thu 1/9

6:55 pm-6:43 pm

2 stops26h 48m

$408

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 1/24

12:45 am-3:13 pm

1 stop10h 28m

San Juan Luis Munoz Marin Intl

Thu 1/30

7:30 am-6:00 pm

1 stop14h 30m

$424

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 5/17

11:10 pm-4:09 pm

1 stop13h 59m

San Juan Luis Munoz Marin Intl

Sat 5/31

1:35 pm-9:55 pm

1 stop11h 20m

$434

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Sat 1/18

5:30 pm-5:39 pm

2 stops20h 09m

Punta Cana

Fri 1/24

4:50 pm-10:55 pm

1 stop34h 05m

$451

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Sat 1/11

10:45 pm-12:27 pm

1 stop9h 42m

Saint Thomas Island Cyril E King

Sat 1/18

6:31 pm-11:06 am

2 stops20h 35m

$458

EugeneSan Juan

EUG - SJU

EUGSJU

Eugene

Sat 2/22

6:00 am-10:22 pm

2 stops12h 22m

San Juan Luis Munoz Marin Intl

Tue 3/4

7:45 am-8:52 pm

2 stops17h 07m

$459

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Tue 2/11

5:30 pm-12:42 pm

2 stops15h 12m

Punta Cana

Wed 2/26

4:48 pm-7:31 pm

3 stops30h 43m

$460

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 54 results
1
2
3
...
6

Best time to book a flight from Oregon to Caribbean Islands

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

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

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

Currently, September is the cheapest month in which you can book a flight from Oregon to Caribbean Islands (average of $254). Flying from Oregon to Caribbean Islands in March is currently the most expensive (average of $380). 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 EPX?

Find hourly flight availability from Oregon to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 23, 2024.

When flying from Oregon to Caribbean Islands, 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 Islands by month

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

In terms of precipitation, rainfall in Caribbean Islands 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 Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

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

If weather is an important factor for your trip to Caribbean Islands, 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 Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated December 23, 2024.
Read through reviews of airlines operating flights from Oregon to Caribbean Islands, such as Delta, Spirit Airlines and United Airlines. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.1
Very good
4,804 reviews

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Boarding

8.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.1
Very good
4,804 reviews
8.1
Very good
4,804 reviews

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Boarding

8.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
8,594 reviews
8.1
Very good
4,804 reviews

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Boarding

8.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
9,537 reviews
8.1
Very good
4,804 reviews

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Boarding

8.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.7
Good
1,713 reviews
8.1
Very good
4,804 reviews

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Boarding

8.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.4
Good
9,028 reviews
8.1
Very good
4,804 reviews

Comfort

8.1

Entertainment

7.7

Food

7.2

Overall

8.1

Boarding

8.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

Find useful and relevant information for your journey from Oregon to Caribbean Islands. 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 Islands one-way?

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $158. American Airlines flights start at $174 while deals on United Airlines start at $182 one-way.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Oregon to Caribbean Islands (average of $254). Flying from Oregon to Caribbean Islands in March is currently the most expensive (average of $380). 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 Islands

See prices for flight routes from nearby airports that may be better suited for you.

Top 9 airlines flying from Oregon to Caribbean Islands

Discover the top 9 airlines that operate flights from Oregon to Caribbean Islands. 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 December 23, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$348FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$217Average$1,713FlexibilityNo cancel feeOn-time75%
Spirit AirlinesCheapest$225Average$362FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$281Average$708FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$288Average$569FlexibilityNo cancel feeOn-time62%
DeltaCheapest$305Average$698FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$325Average$759FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$504Average$864FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$507Average$717FlexibilityNo cancel feeOn-time83%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.