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Oregon

$209+ 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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
dic. 3 — dic. 101
mié. 12/3
mié. 12/10
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 noviembre 3, 2025.

Round-trip from

$397
(Southwest)

One-way from

$209
(Kiwi.com)

Popular in

November

Cheapest in

February

Average price

$685
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. 13% potential increase in price ($85 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in November 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 noviembre 3, 2025.

This Southwest deal was found by Cheapflights users on 11/2. 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.
mar. 12/22:05 pmSJU - PDX
2 stops12h 30mSouthwest
mar. 12/96:55 pmPDX - SJU
2 stops11h 30mSouthwest
Deal found 11/2$397
This United Airlines deal was found by Cheapflights users on 11/3. 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.
lun. 12/82:10 pmSJU - PDX
1 stop11h 35mUnited Airlines
jue. 12/115:00 amPDX - SJU
2 stops13h 22mUnited Airlines
Deal found 11/3$419
This American Airlines deal was found by Cheapflights users on 11/2. 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.
lun. 12/2210:25 amSJU - PDX
1 stop18h 34mAmerican Airlines
mar. 1/611:01 pmPDX - SJU
1 stop14h 00mAmerican Airlines
Deal found 11/2$427
This American Airlines deal was found by Cheapflights users on 11/2. 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.
mar. 11/183:56 pmSJU - PDX
1 stop11h 30mAmerican Airlines
jue. 12/410:15 pmPDX - SJU
1 stop19h 54mAmerican Airlines
Deal found 11/2$482
This eDestinos deal was found by Cheapflights users on 11/3. 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.
mar. 12/233:55 amSJU - PDX
2 stops35h 48mMultiple Airlines
vie. 1/211:20 pmPDX - SJU
1 stop27h 14mMultiple Airlines
Deal found 11/3$492
This eDestinos deal was found by Cheapflights users on 11/3. 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.
lun. 12/225:22 pmSJU - PDX
2 stops31h 48mMultiple Airlines
mar. 1/66:14 amPDX - SJU
2 stops29h 59mMultiple Airlines
Deal found 11/3$496
This American Airlines deal was found by Cheapflights users on 11/3. 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.
mié. 12/2410:25 amSJU - PDX
1 stop18h 34mAmerican Airlines
vie. 1/23:02 pmPDX - SJU
1 stop9h 58mAmerican Airlines
Deal found 11/3$501
This Southwest deal was found by Cheapflights users on 11/3. 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.
lun. 12/88:55 amSJU - PDX
2 stops14h 25mSouthwest
jue. 12/116:15 amPDX - SJU
2 stops11h 50mSouthwest
Deal found 11/3$520
This Gotogate deal was found by Cheapflights users on 11/3. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/77:05 pmMBJ - PDX
2 stops41h 10mAir Canada
vie. 11/283:15 pmPDX - MBJ
2 stops18h 55mAir Canada
Deal found 11/3$657
This Delta deal was found by Cheapflights users on 11/3. 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.
vie. 11/72:32 pmMBJ - PDX
1 stop10h 36mDelta
vie. 11/285:26 pmPDX - MBJ
2 stops18h 04mDelta
Deal found 11/3$659
This United Airlines deal was found by Cheapflights users on 11/2. 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.
mié. 12/175:45 pmGCM - PDX
2 stops26h 46mUnited Airlines
mié. 12/2410:52 pmPDX - GCM
1 stop14h 43mUnited Airlines
Deal found 11/2$674
This American Airlines deal was found by Cheapflights users on 11/3. 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.
vie. 11/712:22 pmMBJ - PDX
1 stop10h 56mAmerican Airlines
vie. 11/281:47 pmPDX - MBJ
1 stop20h 13mAmerican Airlines
Deal found 11/3$680

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 noviembre 3, 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

mar. 12/2

2:05 pm-10:35 pm

2 stops12h 30m

Portland

mar. 12/9

6:55 pm-10:25 am

2 stops11h 30m

$397

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

lun. 12/8

2:10 pm-9:45 pm

1 stop11h 35m

Portland

jue. 12/11

5:00 am-10:22 pm

2 stops13h 22m

$419

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

jue. 2/26

6:15 am-6:50 pm

2 stops16h 35m

Portland

lun. 3/2

7:00 am-11:58 pm

1 stop12h 58m

$419

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

lun. 12/22

10:25 am-12:59 am

1 stop18h 34m

Portland

mar. 1/6

11:01 pm-5:01 pm

1 stop14h 00m

$427

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

mar. 11/18

2:47 pm-11:31 pm

1 stop12h 44m

Portland

jue. 12/4

10:15 pm-10:09 pm

1 stop19h 54m

$482

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

mié. 2/25

2:05 am-2:48 pm

2 stops16h 43m

Portland

lun. 3/2

3:50 pm-2:40 pm

2 stops18h 50m

$499

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

lun. 12/8

8:55 am-7:20 pm

2 stops14h 25m

Portland

jue. 12/11

6:15 am-10:05 pm

2 stops11h 50m

$520

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

vie. 11/14

7:45 am-8:38 pm

2 stops16h 53m

Portland

vie. 11/14

11:59 pm-3:40 pm

1 stop11h 41m

$540

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

sáb. 2/28

8:00 am-10:39 pm

1 stop17h 39m

Portland

mar. 3/3

9:45 pm-3:15 pm

1 stop14h 30m

$543

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

sáb. 2/28

3:20 pm-12:38 pm

2 stops24h 18m

Portland

mar. 3/3

11:59 pm-1:46 pm

1 stop10h 47m

$543

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 57 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, September is the cheapest month in which you can book a flight from Caribbean to Oregon (average of $228). Flying from Caribbean to Oregon in October is currently the most expensive (average of $488). 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 noviembre 3, 2025.

When flying from Caribbean to Oregon, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 22% versus a flight at noon.

What is the cheapest day to fly from Caribbean to Oregon?

Use this chart to determine the cheapest time to fly round-trip from Caribbean to Oregon. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Caribbean to Oregon flight should consider departing on Saturday afternoons when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 noviembre 3, 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
4,238 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

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
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

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
7.9
Good
8,002 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

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
8,997 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

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
11,038 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

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?

    Southwest, United Airlines, and Delta can get you from Caribbean to Oregon in just under 11h 35m. Your travel time can differ by up to 5h. The distance between Caribbean and Oregon is about 3710 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 Frontier ($209), Delta ($300), and United Airlines ($300).

  • 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, September is the cheapest month in which you can book a flight from Caribbean to Oregon (average of $228). Flying from Caribbean to Oregon in October is currently the most expensive (average of $488). 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 noviembre 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$242Average$522FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$349Average$497FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$406Average$573FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$466Average$565FlexibilityNo cancel feeOn-time63%

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