Oregon

$186+ 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 6/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
May 21 — May 281
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Cheap 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 April 21, 2026.

This United Airlines deal was found by Cheapflights users on 4/18. 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 6/22:40 pm
MBJ
-
PDX
2 stops20h 59m
United Airlines
Tue 6/95:00 pm
PDX
-
MBJ
2 stops20h 10m
United Airlines
Deal found 4/18$426
This Southwest deal was found by Cheapflights users on 4/16. 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 8/208:55 pm
SJU
-
PDX
2 stops17h 45m
Southwest
Mon 8/2410:45 pm
PDX
-
SJU
1 stop11h 05m
Southwest
Deal found 4/16$466
This Delta deal was found by Cheapflights users on 4/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/72:35 pm
SJU
-
PDX
1 stop10h 27m
Delta
Tue 5/127:00 am
PDX
-
SJU
1 stop13h 35m
Delta
Deal found 4/20$496
This Southwest deal was found by Cheapflights users on 4/16. 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 9/2411:35 am
SJU
-
PDX
2 stops12h 35m
Southwest
Sun 9/2710:45 pm
PDX
-
SJU
2 stops12h 00m
Southwest
Deal found 4/16$498
This United Airlines deal was found by Cheapflights users on 4/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/44:12 pm
MBJ
-
PDX
2 stops19h 27m
United Airlines
Thu 6/1111:30 pm
PDX
-
MBJ
1 stop13h 40m
United Airlines
Deal found 4/20$514
This Southwest deal was found by Cheapflights users on 4/20. 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.
Wed 8/1211:50 am
SJU
-
BOI
2 stops12h 35m
Southwest
Wed 8/196:25 am
BOI
-
SJU
2 stops13h 35m
Southwest
Deal found 4/20$526
This American Airlines deal was found by Cheapflights users on 4/17. 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.
Tue 8/183:44 pm
SJU
-
PDX
1 stop10h 23m
American Airlines
Tue 8/256:35 am
PDX
-
SJU
2 stops14h 24m
American Airlines
Deal found 4/17$530
This American Airlines deal was found by Cheapflights users on 4/17. 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.
Tue 8/251:38 pm
SJU
-
PDX
2 stops12h 29m
American Airlines
Wed 9/211:59 pm
PDX
-
SJU
1 stop11h 55m
American Airlines
Deal found 4/17$535
This American Airlines deal was found by Cheapflights users on 4/19. 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 4/1910:17 am
MBJ
-
PDX
1 stop12h 46m
American Airlines
Mon 4/2010:28 pm
PDX
-
MBJ
1 stop11h 23m
American Airlines
Deal found 4/19$545
This American Airlines deal was found by Cheapflights users on 4/16. 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.
Tue 7/217:25 am
SJU
-
PDX
1 stop19h 28m
American Airlines
Mon 7/2710:30 pm
PDX
-
SJU
1 stop12h 03m
American Airlines
Deal found 4/16$548
This American Airlines deal was found by Cheapflights users on 4/18. 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 5/227:00 am
SJU
-
PDX
1 stop19h 59m
American Airlines
Wed 5/276:15 am
PDX
-
SJU
2 stops13h 30m
American Airlines
Deal found 4/18$553
This FlightHub deal was found by Cheapflights users on 4/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2312:25 pm
GCM
-
PDX
2 stops23h 06m
Air Canada
Wed 7/293:30 pm
PDX
-
GCM
2 stops17h 55m
Air Canada
Deal found 4/20$558

Find flight deals from Caribbean to Oregon

Keep the following information in mind while searching for Caribbean to Oregon flight deals. Data was last updated April 21, 2026.

Round-trip from

$356
(American Airlines)

One-way from

$186
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$541
From Caribbean to Oregon
One-way flight from Caribbean to Oregon
Highest demand for flights based on searches. 2% potential increase in price ($14 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Average for round-trip flights in April 2026

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 April 21, 2026.
Use the filters below to find and compare flights from Caribbean to Oregon that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Tue 6/2

2:40 pm-9:39 am

2 stops20h 59m

Portland

Tue 6/9

11:30 pm-3:10 pm

1 stop13h 40m

$426

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Wed 5/6

2:03 pm-11:57 pm

2 stops12h 54m

Portland

Sun 5/10

5:51 pm-12:01 pm

2 stops15h 10m

$496

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 5/7

2:35 pm-10:02 pm

1 stop10h 27m

Portland

Tue 5/12

7:00 am-11:35 pm

1 stop13h 35m

$496

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 9/24

5:30 am-3:00 pm

1 stop12h 30m

Portland

Sun 9/27

10:45 pm-2:30 pm

1 stop12h 45m

$498

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Thu 6/4

12:31 pm-11:59 pm

1 stop13h 28m

Portland

Thu 6/11

10:59 pm-1:24 pm

1 stop12h 25m

$514

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Fri 6/5

2:30 pm-11:56 pm

1 stop11h 26m

Portland

Thu 6/11

12:40 am-4:17 pm

1 stop13h 37m

$514

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Thu 6/4

4:12 pm-9:39 am

2 stops19h 27m

Portland

Thu 6/11

11:30 pm-3:10 pm

1 stop13h 40m

$514

San JuanBoise

SJU - BOI

SJUBOI

San Juan Luis Munoz Marin Intl

Wed 8/12

11:50 am-10:25 pm

2 stops12h 35m

Boise Air Term. Gowen Fld

Wed 8/19

6:25 am-10:00 pm

2 stops13h 35m

$526

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 9/24

5:30 am-3:00 pm

1 stop12h 30m

Portland

Sat 9/26

10:45 pm-5:05 pm

2 stops15h 20m

$530
Quickest round-trip

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 9/24

2:55 pm-10:59 pm

1 stop11h 04m

Portland

Sat 9/26

10:56 pm-11:57 am

1 stop10h 01m

$530

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/20

Showing 1-10 of 60 resultsSorted by cheapest first
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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, June is the cheapest month in which you can book a flight from Caribbean to Oregon (average of $185). Flying from Caribbean to Oregon in January is currently the most expensive (average of $447). 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.

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 April 21, 2026.
Peruse reviews from past customers who have flown with Delta,United Airlines, andAmerican Airlines 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.

Crew

8.5

Overall

7.9

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Crew

8.5

Overall

7.9

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Crew

8.5

Overall

7.9

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Crew

8.5

Overall

7.9

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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.
  • How long is the flight from Caribbean to Oregon?

    American Airlines, United Airlines, and Southwest can get you from Caribbean to Oregon in just under 11h 34m. Your travel time can differ by up to 9h 25m. The distance between Caribbean and Oregon is about 3155 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 ($149), JetBlue ($185), and American Airlines ($212).

  • 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, June is the cheapest month in which you can book a flight from Caribbean to Oregon (average of $185). Flying from Caribbean to Oregon in January is currently the most expensive (average of $447). 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.

Top 3 airlines flying from Caribbean to Oregon

Discover the top 3 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 April 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$184Average$522FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$406Average$567FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$419Average$550FlexibilityNo cancel feeOn-time71%

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