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Oregon

$193+ Cheap flights from Caribbean to Oregon

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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
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Cheap flight deals from Caribbean to Oregon

Keep the following information in mind while searching for Caribbean to Oregon flight deals. Data was last updated July 30, 2025.

Round-trip from

$399
(Delta)

One-way from

$193
(Delta)

Popular in

November

Cheapest in

February

Average price

$565
From Caribbean to Oregon
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One-way flight from Caribbean to Oregon
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Highest demand for flights based on searches. 9% potential increase in price ($52 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 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 Caribbean to Oregon

Cheapest flights from Caribbean to Oregon
Explore the most affordable flight options available from Caribbean to Oregon. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 30, 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.
Sat 10/117:15 amSJU - PDX
2 stops18h 12mDelta
Fri 10/1710:58 pmPDX - SJU
1 stop10h 54mDelta
Deal found 7/28$399
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.
Fri 8/292:55 pmSJU - PDX
1 stop21h 29mAmerican Airlines
Sun 8/317:40 amPDX - SJU
2 stops13h 19mAmerican Airlines
Deal found 7/28$408
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 9/1111:59 amSJU - PDX
3 stops26h 13mSpirit Airlines
Thu 9/188:04 pmPDX - SJU
2 stops19h 30mSpirit Airlines
Deal found 7/28$428
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.
Thu 9/1111:59 amSJU - PDX
3 stops26h 13mMultiple Airlines
Thu 9/188:04 pmPDX - SJU
3 stops25h 40mMultiple Airlines
Deal found 7/29$434
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/191:05 amSJU - PDX
1 stop11h 18mUnited Airlines
Fri 10/35:00 amPDX - SJU
1 stop9h 30mUnited Airlines
Deal found 7/28$489
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.
Wed 9/106:10 amSJU - BOI
2 stops18h 44mAmerican Airlines
Sun 9/147:00 amBOI - SJU
2 stops14h 37mAmerican Airlines
Deal found 7/29$511
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.
Thu 8/285:50 amSJU - PDX
1 stop13h 10mSouthwest
Sun 8/319:05 pmPDX - SJU
1 stop12h 35mSouthwest
Deal found 7/29$557
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/142:50 pmMBJ - PDX
3 stops30h 33mMultiple Airlines
Sun 9/2112:07 pmPDX - MBJ
3 stops20h 58mMultiple Airlines
Deal found 7/30$575
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.
Sun 9/143:36 pmMBJ - PDX
2 stops20h 01mAmerican Airlines
Sun 9/219:56 pmPDX - MBJ
2 stops12h 09mAmerican Airlines
Deal found 7/30$596
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/107:30 amSJU - BOI
2 stops18h 28mDelta
Sun 9/1411:35 pmBOI - SJU
1 stop11h 41mDelta
Deal found 7/29$619
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.
Tue 8/2612:32 pmKIN - PDX
3 stops32h 25mMultiple Airlines
Wed 9/37:52 pmPDX - KIN
3 stops22h 13mMultiple Airlines
Deal found 7/28$632
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/91:45 pmKIN - PDX
2 stops27h 01mAir Canada
Tue 9/163:25 pmPDX - KIN
2 stops19h 10mAir Canada
Deal found 7/29$640

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean to Oregon 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 30, 2025.
Use the filters below to find and compare flights from Caribbean to Oregon that are best for you.

Fly from

Caribbean

Fly to

Oregon

Route

Depart

Return

Price

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Sat 10/11

7:15 am-10:27 pm

2 stops18h 12m

Portland

Fri 10/17

10:58 pm-12:52 pm

1 stop10h 54m

$399

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Fri 8/29

2:55 pm-9:24 am

1 stop21h 29m

Portland

Sun 8/31

7:40 am-11:59 pm

2 stops13h 19m

$408

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 9/11

11:59 am-11:12 am

3 stops26h 13m

Portland

Thu 9/18

8:04 pm-6:34 pm

2 stops19h 30m

$428

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 9/11

11:59 am-11:12 am

3 stops26h 13m

Portland

Thu 9/18

8:04 pm-12:44 am

3 stops25h 40m

$434

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Fri 9/19

1:05 am-9:23 am

1 stop11h 18m

Portland

Fri 10/3

5:00 am-5:30 pm

1 stop9h 30m

$489

San JuanBoise

SJU - BOI

SJUBOI

San Juan Luis Munoz Marin Intl

Wed 9/10

6:10 am-10:54 pm

2 stops18h 44m

Boise Air Term. Gowen Fld

Sun 9/14

7:00 am-11:37 pm

2 stops14h 37m

$511

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 8/28

5:50 am-4:00 pm

1 stop13h 10m

Portland

Sun 8/31

9:05 pm-12:40 pm

1 stop12h 35m

$557

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Sun 9/14

2:50 pm-7:23 pm

3 stops30h 33m

Portland

Sun 9/21

12:07 pm-11:05 am

3 stops20h 58m

$575

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Sun 9/14

3:36 pm-9:37 am

2 stops20h 01m

Portland

Sun 9/21

9:56 pm-12:05 pm

2 stops12h 09m

$596

San JuanBoise

SJU - BOI

SJUBOI

San Juan Luis Munoz Marin Intl

Wed 9/10

7:30 am-11:58 pm

2 stops18h 28m

Boise Air Term. Gowen Fld

Sun 9/14

11:35 pm-1:16 pm

1 stop11h 41m

$619

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 42 results
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Best time to book a flight from Caribbean to Oregon

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

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

Currently, November is the cheapest month in which you can book a flight from Caribbean to Oregon (average of $277). Flying from Caribbean to Oregon in March is currently the most expensive (average of $368). 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 CB to OR?

Find hourly flight availability from Caribbean to Oregon. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 30, 2025.

When flying from Caribbean to Oregon, 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 Oregon

Get insights into the airlines that provide service to Oregon. 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 Oregon. Reviews last updated July 30, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest, and Delta from Caribbean to Oregon 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

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

YEG - SEA

Alaska airline excellent airline pilot smooth, landing, crew staff very nice friendly behave
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

YEG - SEA

Alaska airline excellent airline pilot smooth, landing, crew staff very nice friendly behave
Southwest
8.0
Very good
4,241 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

YEG - SEA

Alaska airline excellent airline pilot smooth, landing, crew staff very nice friendly behave
Delta
8.0
Very good
7,980 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

YEG - SEA

Alaska airline excellent airline pilot smooth, landing, crew staff very nice friendly behave
United Airlines
7.4
Good
8,896 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

YEG - SEA

Alaska airline excellent airline pilot smooth, landing, crew staff very nice friendly behave
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2025

YEG - SEA

Alaska airline excellent airline pilot smooth, landing, crew staff very nice friendly behave

Related info for your journey

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

    The cheapest airlines for a one-way flight from Caribbean to Oregon are Delta ($193), American Airlines ($204), and Southwest ($206).

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

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

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

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

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

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

    Currently, November is the cheapest month in which you can book a flight from Caribbean to Oregon (average of $277). Flying from Caribbean to Oregon in March is currently the most expensive (average of $368). 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 Caribbean to Oregon

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Caribbean to Oregon

Discover the top 5 airlines that operate flights from Caribbean to Oregon. 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 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$232Average$394FlexibilityNo cancel feeOn-time62%
DeltaCheapest$290Average$516FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$348Average$586FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$406Average$632FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$424Average$565FlexibilityNo cancel feeOn-time63%

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