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Caribbean

$188+ 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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$375
(Delta)

One-way from

$188
(Delta)

Popular in

March

Cheapest in

October

Average price

$580
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. 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

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 July 29, 2025.

This Delta deal was found by Cheapflights users on 7/28. 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 10/214:46 pmBOI - SJU
2 stops17h 14mDelta
Tue 10/287:15 amSJU - BOI
2 stops18h 44mDelta
Deal found 7/28$375
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/96:00 amPDX - SJU
2 stops13h 30mSouthwest
Fri 9/195:50 amSJU - PDX
1 stop13h 10mSouthwest
Deal found 7/29$389
This Delta deal was found by Cheapflights users on 7/27. 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 9/287:15 amPDX - SJU
1 stop13h 32mDelta
Sat 10/42:26 pmSJU - PDX
1 stop10h 21mDelta
Deal found 7/27$399
This Mytrip deal was found by Cheapflights users on 7/28. 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.
Thu 9/2512:07 pmPDX - SJU
3 stops33h 37mSpirit Airlines
Sun 9/282:48 pmSJU - PDX
2 stops31h 16mSpirit Airlines
Deal found 7/28$403
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.
Sat 9/61:57 pmBOI - SJU
2 stops19h 14mAmerican Airlines
Sat 9/137:05 pmSJU - BOI
2 stops19h 22mAmerican Airlines
Deal found 7/29$415
This American Airlines deal was found by Cheapflights users on 7/28. 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 11/610:45 pmPDX - SJU
1 stop10h 56mAmerican Airlines
Thu 11/136:44 amSJU - PDX
2 stops14h 28mAmerican Airlines
Deal found 7/28$419
This Mytrip deal was found by Cheapflights users on 7/26. 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 8/156:06 pmBOI - SJU
3 stops27h 51mSpirit Airlines
Thu 8/214:12 pmSJU - BOI
3 stops26h 59mSpirit Airlines
Deal found 7/26$426
This Frontier deal was found by Cheapflights users on 7/28. 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.
Sat 8/27:01 pmPDX - SJU
2 stops17h 51mFrontier
Wed 8/139:30 amSJU - PDX
2 stops16h 54mFrontier
Deal found 7/28$440
This Mytrip deal was found by Cheapflights users on 7/28. 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 9/208:04 pmPDX - SJU
2 stops15h 57mMultiple Airlines
Sat 9/273:19 pmSJU - PDX
3 stops28h 15mMultiple Airlines
Deal found 7/28$476
This American Airlines deal was found by Cheapflights users on 7/27. 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 10/1111:58 pmPDX - PUJ
1 stop11h 07mAmerican Airlines
Fri 10/173:21 pmPUJ - PDX
1 stop21h 10mAmerican Airlines
Deal found 7/27$487
This American Airlines deal was found by Cheapflights users on 7/26. 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.
Fri 12/56:44 pmPDX - STX
2 stops16h 11mAmerican Airlines
Sat 12/134:35 pmSTX - PDX
1 stop10h 41mAmerican Airlines
Deal found 7/26$489
This American Airlines deal was found by Cheapflights users on 7/28. 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 10/189:52 pmPDX - NAS
1 stop9h 08mAmerican Airlines
Tue 10/2111:40 amNAS - PDX
1 stop11h 34mAmerican Airlines
Deal found 7/28$489

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 July 29, 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

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Tue 10/21

4:46 pm-12:00 pm

2 stops17h 14m

San Juan Luis Munoz Marin Intl

Tue 10/28

7:15 am-11:59 pm

2 stops18h 44m

$375

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 9/9

6:00 am-10:30 pm

2 stops13h 30m

San Juan Luis Munoz Marin Intl

Fri 9/19

5:50 am-4:00 pm

1 stop13h 10m

$389

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 1/20

12:55 am-3:20 pm

1 stop10h 25m

San Juan Luis Munoz Marin Intl

Wed 1/28

7:00 am-7:11 pm

2 stops16h 11m

$399

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 9/25

12:07 pm-12:44 am

3 stops33h 37m

San Juan Luis Munoz Marin Intl

Sun 9/28

2:48 pm-7:04 pm

2 stops31h 16m

$403

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 11/6

10:45 pm-1:41 pm

1 stop10h 56m

San Juan Luis Munoz Marin Intl

Thu 11/13

6:44 am-5:12 pm

2 stops14h 28m

$419

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Fri 8/15

6:06 pm-11:57 pm

3 stops27h 51m

San Juan Luis Munoz Marin Intl

Thu 8/21

4:12 pm-5:11 pm

3 stops26h 59m

$426

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 9/20

8:04 pm-3:01 pm

2 stops15h 57m

San Juan Luis Munoz Marin Intl

Sat 9/27

3:19 pm-4:34 pm

3 stops28h 15m

$476

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Sat 10/11

11:58 pm-2:05 pm

1 stop11h 07m

Punta Cana

Fri 10/17

3:21 pm-9:31 am

1 stop21h 10m

$487

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 9/16

10:50 pm-1:45 pm

1 stop11h 55m

San Juan Luis Munoz Marin Intl

Tue 9/23

1:25 pm-9:37 pm

1 stop11h 12m

$489

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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 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 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 July 29, 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.

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 July 29, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest, and Delta from Oregon to Caribbean to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Food

7.1

Overall

8.0

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

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Food

7.1

Overall

8.0

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
4,238 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Food

7.1

Overall

8.0

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
7,977 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Food

7.1

Overall

8.0

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
8,899 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Food

7.1

Overall

8.0

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.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Food

7.1

Overall

8.0

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. 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 Delta. According to our data, you can fly for as low as $188. Users have also found prices from $189 and $200 on Spirit Airlines 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 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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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 7 airlines flying from Oregon to Caribbean

Discover the top 7 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 July 29, 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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