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Caribbean Islands

$146+ 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 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap flight deals from Oregon to Caribbean Islands

Keep the following information in mind while searching for Oregon to Caribbean Islands flight deals. Data was last updated July 31, 2025.

Round-trip from

$370
(Booking.com)

One-way from

$146
(Booking.com)

Popular in

March

Cheapest in

October

Average price

$580
From Oregon to Caribbean Islands
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One-way flight from Oregon to Caribbean Islands
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Highest demand for flights based on searches. 8% potential increase in price ($53 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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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 July 31, 2025.

This Booking.com deal was found by Cheapflights users on 7/30. 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 10/278:58 pmBOI - SJU
2 stops19h 36mSpirit Airlines
Fri 10/317:40 pmSJU - BOI
2 stops19h 41mSpirit Airlines
Deal found 7/30$370
This Southwest deal was found by Cheapflights users on 7/30. 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.
Tue 11/185:15 amBOI - SJU
2 stops10h 20mSouthwest
Fri 11/216:40 amSJU - BOI
2 stops12h 30mSouthwest
Deal found 7/30$375
This Delta deal was found by Cheapflights users on 7/30. 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 10/274:46 pmBOI - SJU
2 stops17h 14mDelta
Fri 10/317:15 amSJU - BOI
2 stops15h 01mDelta
Deal found 7/30$385
This Southwest deal was found by Cheapflights users on 7/31. 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.
Mon 11/107:10 pmPDX - SJU
2 stops11h 15mSouthwest
Tue 12/98:55 amSJU - PDX
2 stops14h 25mSouthwest
Deal found 7/31$389
This Mytrip deal was found by Cheapflights users on 7/29. 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.
Wed 10/158:04 pmPDX - SJU
3 stops25h 39mSpirit Airlines
Thu 10/302:48 pmSJU - PDX
3 stops31h 16mSpirit Airlines
Deal found 7/29$393
This Delta deal was found by Cheapflights users on 7/31. 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.
Tue 9/95:30 amPDX - SJU
2 stops15h 21mDelta
Sat 9/137:00 amSJU - PDX
2 stops18h 42mDelta
Deal found 7/31$409
This Southwest deal was found by Cheapflights users on 7/31. 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.
Mon 11/102:55 pmEUG - SJU
2 stops18h 20mSouthwest
Tue 12/98:55 amSJU - EUG
2 stops16h 20mSouthwest
Deal found 7/31$411
This American Airlines deal was found by Cheapflights users on 7/31. 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 9/61:57 pmBOI - SJU
2 stops19h 14mAmerican Airlines
Sat 9/137:05 pmSJU - BOI
2 stops19h 22mAmerican Airlines
Deal found 7/31$415
This American Airlines deal was found by Cheapflights users on 7/29. 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 10/3011:58 pmPDX - SJU
1 stop12h 42mAmerican Airlines
Thu 11/272:41 pmSJU - PDX
1 stop12h 26mAmerican Airlines
Deal found 7/29$419
This Priceline deal was found by Cheapflights users on 7/31. 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.
Fri 11/76:36 pmPDX - SJU
1 stop17h 38mMultiple Airlines
Fri 11/146:00 amSJU - PDX
2 stops19h 36mMultiple Airlines
Deal found 7/31$425
This United Airlines deal was found by Cheapflights users on 7/29. 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 9/97:04 amPDX - SJU
1 stop10h 34mUnited Airlines
Fri 9/191:25 pmSJU - PDX
1 stop11h 12mUnited Airlines
Deal found 7/29$428
This American Airlines deal was found by Cheapflights users on 7/30. 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 9/139:56 pmPDX - NAS
1 stop12h 09mAmerican Airlines
Sat 9/202:09 pmNAS - PDX
1 stop9h 28mAmerican Airlines
Deal found 7/30$439

Cheapflights Fare Finder

 
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 July 31, 2025.
Use the filters below to find and compare flights from Oregon to Caribbean Islands that are best for you.

Fly from

Oregon

Fly to

Caribbean Islands

Route

Depart

Return

Price

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Mon 10/27

8:58 pm-6:34 pm

2 stops19h 36m

San Juan Luis Munoz Marin Intl

Fri 10/31

7:40 pm-1:21 pm

2 stops19h 41m

$370

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Tue 11/18

5:15 am-6:35 pm

2 stops10h 20m

San Juan Luis Munoz Marin Intl

Fri 11/21

6:40 am-4:10 pm

2 stops12h 30m

$375

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Wed 1/21

5:40 am-11:58 pm

2 stops15h 18m

San Juan Luis Munoz Marin Intl

Tue 1/27

7:00 am-6:25 pm

2 stops14h 25m

$385

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 11/10

7:10 pm-10:25 am

2 stops11h 15m

San Juan Luis Munoz Marin Intl

Tue 12/9

8:55 am-7:20 pm

2 stops14h 25m

$389

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 10/15

8:04 pm-12:43 am

3 stops25h 39m

San Juan Luis Munoz Marin Intl

Thu 10/30

2:48 pm-7:04 pm

3 stops31h 16m

$393

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 9/9

5:30 am-11:51 pm

2 stops15h 21m

San Juan Luis Munoz Marin Intl

Sat 9/13

7:00 am-10:42 pm

2 stops18h 42m

$409

EugeneSan Juan

EUG - SJU

EUGSJU

Eugene

Mon 11/10

2:55 pm-1:15 pm

2 stops18h 20m

San Juan Luis Munoz Marin Intl

Tue 12/9

8:55 am-9:15 pm

2 stops16h 20m

$411

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Sat 9/6

1:57 pm-11:11 am

2 stops19h 14m

San Juan Luis Munoz Marin Intl

Sat 9/13

7:05 pm-12:27 pm

2 stops19h 22m

$415

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 10/30

11:58 pm-3:40 pm

1 stop12h 42m

San Juan Luis Munoz Marin Intl

Sun 12/7

5:50 am-11:16 pm

1 stop21h 26m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 11/7

6:36 pm-4:14 pm

1 stop17h 38m

San Juan Luis Munoz Marin Intl

Fri 11/14

6:00 am-9:36 pm

2 stops19h 36m

$425

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 57 results
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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.

Cheapflights Insights

Everything you need to know about your flight from Oregon to Caribbean Islands

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 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 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 July 31, 2025.

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.

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 July 31, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest, and Delta from Oregon to Caribbean Islands to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
LATAM Airlines
7.5
Good
1,822 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,900 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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 $146. Delta flights start at $193 while deals on United Airlines start at $200 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 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.

See more FAQs

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Top 7 airlines flying from Oregon to Caribbean Islands

Discover the top 7 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$369FlexibilityNo cancel feeOn-time62%
DeltaCheapest$202Average$676FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$248Average$379FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$318Average$698FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$328Average$705FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$450Average$728FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$454Average$599FlexibilityNo cancel feeOn-time75%

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