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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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$419
(Delta)

One-way from

$186
(Kiwi.com)

Popular in

November

Cheapest in

February

Average price

$479
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. 11% potential increase in price ($65 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 17, 2025.

This American Airlines deal was found by Cheapflights users on 9/15. 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 10/283:00 pmSJU - PDX
1 stop11h 06mAmerican Airlines
Tue 11/410:45 pmPDX - SJU
1 stop10h 58mAmerican Airlines
Deal found 9/15$419
This Southwest deal was found by Cheapflights users on 9/16. 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 10/305:50 amSJU - PDX
2 stops14h 30mSouthwest
Tue 11/48:00 amPDX - SJU
2 stops12h 35mSouthwest
Deal found 9/16$450
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/287:05 amSJU - PDX
2 stops12h 59mAmerican Airlines
Tue 11/115:42 pmPDX - SJU
2 stops14h 23mAmerican Airlines
Deal found 9/15$457
This Sun Country Air deal was found by Cheapflights users on 9/15. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/219:00 amSJU - PDX
1 stop11h 30mSun Country Air
Fri 9/266:24 pmPDX - SJU
1 stop17h 47mSun Country Air
Deal found 9/15$459
This eDestinos deal was found by Cheapflights users on 9/15. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/61:59 amSJU - PDX
3 stops36h 49mMultiple Airlines
Sat 10/115:38 pmPDX - SJU
2 stops18h 46mMultiple Airlines
Deal found 9/15$464
This Frontier deal was found by Cheapflights users on 9/15. 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 9/229:07 amSJU - PDX
2 stops18h 05mFrontier
Sat 9/278:02 amPDX - SJU
2 stops22h 50mFrontier
Deal found 9/15$470
This Delta deal was found by Cheapflights users on 9/15. 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 10/71:06 pmSJU - PDX
2 stops13h 51mDelta
Sat 10/117:12 amPDX - SJU
1 stop13h 44mDelta
Deal found 9/15$482
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Sat 10/113:00 pmSJU - PDX
1 stop11h 06mAmerican Airlines
Tue 10/1411:59 pmPDX - SJU
2 stops12h 55mAmerican Airlines
Deal found 9/16$492
This Mytrip deal was found by Cheapflights users on 9/15. 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 10/16:44 amSJU - PDX
2 stops31h 27mMultiple Airlines
Sun 10/56:16 pmPDX - SJU
2 stops29h 35mMultiple Airlines
Deal found 9/15$493
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/143:00 pmSJU - PDX
1 stop21h 31mAmerican Airlines
Wed 10/225:05 amPDX - SJU
2 stops14h 05mAmerican Airlines
Deal found 9/16$495
This Delta deal was found by Cheapflights users on 9/14. 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 10/301:32 pmMBJ - PDX
1 stop10h 36mDelta
Thu 11/63:19 pmPDX - MBJ
2 stops18h 04mDelta
Deal found 9/14$533
This United Airlines deal was found by Cheapflights users on 9/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/12:36 pmMBJ - PDX
2 stops22h 02mUnited Airlines
Sat 11/87:38 pmPDX - MBJ
2 stops15h 27mUnited Airlines
Deal found 9/17$541

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 September 17, 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

Tue 10/7

1:06 pm-11:57 pm

2 stops13h 51m

Portland

Sat 10/18

7:12 am-11:56 pm

1 stop13h 44m

$419

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 2/26

7:30 am-8:47 pm

2 stops17h 17m

Portland

Mon 3/2

9:45 pm-1:00 pm

1 stop11h 15m

$419

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 10/30

12:46 pm-10:08 pm

1 stop12h 22m

Portland

Tue 11/4

7:12 am-12:56 am

1 stop13h 44m

$419

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 10/9

1:06 pm-11:57 pm

2 stops13h 51m

Portland

Fri 10/17

12:40 am-4:25 pm

2 stops12h 45m

$482

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Tue 10/28

7:00 am-10:27 pm

2 stops18h 27m

Portland

Mon 11/10

12:35 am-5:20 pm

2 stops12h 45m

$482

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Thu 10/30

1:32 pm-10:08 pm

1 stop10h 36m

Portland

Thu 11/6

3:19 pm-12:23 pm

2 stops18h 04m

$533

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Sat 11/1

2:20 pm-11:58 am

3 stops23h 38m

Portland

Sat 11/8

7:38 pm-2:05 pm

2 stops15h 27m

$541

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Thu 10/30

1:00 pm-11:08 pm

1 stop12h 08m

Portland

Thu 11/6

10:45 pm-2:12 pm

1 stop12h 27m

$542

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Thu 10/30

1:48 pm-9:38 am

2 stops21h 50m

Portland

Thu 11/6

7:10 pm-2:05 pm

2 stops39h 55m

$542

Punta CanaPortland

PUJ - PDX

PUJPDX

Punta Cana

Thu 2/19

2:05 pm-9:18 pm

1 stop11h 13m

Portland

Sun 2/22

10:56 pm-1:49 pm

1 stop10h 53m

$542

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 39 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 September 17, 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 September 17, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United 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.
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,961 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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?

    Delta, United Airlines, and American Airlines can get you from Caribbean to Oregon in just under 12h 08m. Your travel time can differ by up to 11h 30m. 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 American Airlines ($210), United Airlines ($210), and Air Canada ($297).

  • 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 4 airlines flying from Caribbean to Oregon

Discover the top 4 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$248Average$512FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$353Average$589FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$406Average$587FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$424Average$565FlexibilityNo cancel feeOn-time63%

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