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Caribbean

$187+ 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 7/13. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$333
(FlightHub)

One-way from

$187
(FlightHub)

Popular in

March

Cheapest in

September

Average price

$635
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 ($74 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 June 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 June 12, 2025.

This FlightHub deal was found by Cheapflights users on 6/12. 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.
Tue 7/812:12 pmPDX - STT
2 stops18h 36mSpirit Airlines
Tue 7/151:25 pmSTT - PDX
2 stops22h 53mSpirit Airlines
Deal found 6/12$333
This FlightHub deal was found by Cheapflights users on 6/10. 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.
Wed 7/163:10 pmPDX - SJU
2 stops16h 19mSpirit Airlines
Tue 7/224:43 pmSJU - PDX
2 stops24h 32mSpirit Airlines
Deal found 6/10$378
This Delta deal was found by Cheapflights users on 6/11. 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.
Sat 8/307:19 amPDX - SJU
1 stop13h 32mDelta
Thu 9/412:50 pmSJU - PDX
1 stop12h 22mDelta
Deal found 6/11$399
This Mytrip deal was found by Cheapflights users on 6/11. 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 7/44:37 pmPDX - SJU
3 stops39h 02mMultiple Airlines
Wed 7/94:43 pmSJU - PDX
2 stops24h 32mMultiple Airlines
Deal found 6/11$406
This United Airlines deal was found by Cheapflights users on 6/10. 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 11/126:15 amBOI - SJU
1 stop9h 10mUnited Airlines
Fri 11/142:05 amSJU - BOI
2 stops14h 20mUnited Airlines
Deal found 6/10$415
This American Airlines deal was found by Cheapflights users on 6/10. 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 11/11:15 pmEUG - SJU
2 stops19h 30mAmerican Airlines
Sat 11/88:14 amSJU - EUG
2 stops15h 07mAmerican Airlines
Deal found 6/10$415
This Delta deal was found by Cheapflights users on 6/10. 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 9/235:30 pmEUG - SJU
2 stops15h 33mDelta
Mon 9/292:15 pmSJU - EUG
2 stops12h 34mDelta
Deal found 6/10$425
This United Airlines deal was found by Cheapflights users on 6/11. 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.
Mon 8/185:00 amPDX - SJU
1 stop9h 30mUnited Airlines
Wed 8/271:05 amSJU - PDX
1 stop10h 48mUnited Airlines
Deal found 6/11$434
This Frontier deal was found by Cheapflights users on 6/11. 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 8/186:35 amPDX - SJU
2 stops15h 11mFrontier
Thu 8/287:25 amSJU - PDX
2 stops19h 50mFrontier
Deal found 6/11$439
This Delta deal was found by Cheapflights users on 6/10. 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.
Fri 7/256:00 pmBOI - SJU
2 stops17h 26mDelta
Tue 7/291:06 pmSJU - BOI
2 stops13h 03mDelta
Deal found 6/10$464
This Southwest deal was found by Cheapflights users on 6/10. 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 9/106:40 pmPDX - SJU
2 stops12h 35mSouthwest
Tue 9/167:20 amSJU - PDX
2 stops14h 05mSouthwest
Deal found 6/10$467
This Mytrip deal was found by Cheapflights users on 6/11. 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 7/93:10 pmPDX - MBJ
3 stops41h 20mSpirit Airlines
Wed 7/1612:10 pmMBJ - PDX
2 stops23h 08mSpirit Airlines
Deal found 6/11$469

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 June 12, 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

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Tue 7/8

12:12 pm-9:48 am

2 stops18h 36m

Saint Thomas Island Cyril E King

Tue 7/15

1:25 pm-9:18 am

2 stops22h 53m

$333

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 7/16

3:10 pm-10:29 am

2 stops16h 19m

San Juan Luis Munoz Marin Intl

Tue 7/22

4:43 pm-2:15 pm

2 stops24h 32m

$378

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 8/30

7:19 am-11:51 pm

1 stop13h 32m

San Juan Luis Munoz Marin Intl

Thu 9/4

12:50 pm-10:12 pm

1 stop12h 22m

$399

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 7/4

4:37 pm-10:39 am

3 stops39h 02m

San Juan Luis Munoz Marin Intl

Wed 7/9

4:43 pm-2:15 pm

2 stops24h 32m

$406

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Wed 11/12

6:15 am-6:25 pm

1 stop9h 10m

San Juan Luis Munoz Marin Intl

Fri 11/14

2:05 am-1:25 pm

2 stops14h 20m

$415

EugeneSan Juan

EUG - SJU

EUGSJU

Eugene

Sat 11/1

1:15 pm-11:45 am

2 stops19h 30m

San Juan Luis Munoz Marin Intl

Sat 11/8

8:14 am-7:21 pm

2 stops15h 07m

$415

EugeneSan Juan

EUG - SJU

EUGSJU

Eugene

Tue 9/23

5:30 pm-12:03 pm

2 stops15h 33m

San Juan Luis Munoz Marin Intl

Mon 9/29

2:15 pm-11:49 pm

2 stops12h 34m

$425

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 8/18

5:00 am-5:30 pm

1 stop9h 30m

San Juan Luis Munoz Marin Intl

Wed 8/27

1:05 am-8:53 am

1 stop10h 48m

$434

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 8/18

6:35 am-12:46 am

2 stops15h 11m

San Juan Luis Munoz Marin Intl

Thu 8/28

7:25 am-12:15 am

2 stops19h 50m

$439

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Fri 7/25

6:00 pm-1:26 pm

2 stops17h 26m

San Juan Luis Munoz Marin Intl

Tue 7/29

1:06 pm-12:09 am

2 stops13h 03m

$464

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

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 June 12, 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 June 12, 2025.
Delta
8.0
Very good
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,946 reviews
Delta
8.0
Very good
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Alaska Airlines
8.0
Very good
10,000 reviews
Delta
8.0
Very good
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Southwest
8.0
Very good
4,287 reviews
Delta
8.0
Very good
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Copa Airlines
7.5
Good
1,451 reviews
Delta
8.0
Very good
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
LATAM Airlines
7.5
Good
1,785 reviews
Delta
8.0
Very good
7,946 reviews

Overall

8.0

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 $187. Users have also found prices from $190 and $200 on JetBlue and Delta, 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

Browse thousands of different options on Cheapflights for your next trip

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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 8 airlines flying from Oregon to Caribbean

Discover the top 8 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$380FlexibilityNo cancel feeOn-time62%
DeltaCheapest$202Average$692FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$248Average$362FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$306Average$705FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$327Average$728FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$431Average$591FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$450Average$713FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$475Average$737FlexibilityNo cancel feeOn-time83%

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