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Oregon

$165+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
Apr 7 — Apr 141
Mon 4/7
Mon 4/14
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 April 2, 2025.

Round-trip from

$369
(American Airlines)

One-way from

$165
(Cheapflightsfares)

Popular in

November

Cheapest in

February

Average price

$523
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. 10% potential increase in price ($58 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 April 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 April 2, 2025.

This American Airlines deal was found by Cheapflights users on 4/1. 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 5/71:10 pmSJU - PDX
1 stop10h 26mAmerican Airlines
Mon 5/129:38 pmPDX - SJU
1 stop19h 55mAmerican Airlines
Deal found 4/1$369
This Delta deal was found by Cheapflights users on 4/1. 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 9/112:28 pmSJU - BOI
1 stop10h 15mDelta
Tue 9/167:30 pmBOI - SJU
2 stops18h 48mDelta
Deal found 4/1$405
This Delta deal was found by Cheapflights users on 4/1. 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 5/281:12 pmSJU - PDX
1 stop13h 03mDelta
Sun 6/18:17 pmPDX - SJU
2 stops13h 28mDelta
Deal found 4/1$416
This Mytrip deal was found by Cheapflights users on 4/1. 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 5/151:33 amSJU - PDX
3 stops38h 09mMultiple Airlines
Fri 5/234:35 pmPDX - SJU
2 stops23h 32mMultiple Airlines
Deal found 4/1$437
This Mytrip deal was found by Cheapflights users on 3/30. 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.
Fri 5/24:44 pmSDQ - PDX
2 stops23h 53mSpirit Airlines
Tue 5/135:40 pmPDX - SDQ
2 stops18h 20mSpirit Airlines
Deal found 3/30$455
This United Airlines deal was found by Cheapflights users on 4/1. 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 5/61:05 amSJU - PDX
2 stops16h 49mUnited Airlines
Mon 5/1210:47 pmPDX - SJU
1 stop10h 10mUnited Airlines
Deal found 4/1$459
This Mytrip deal was found by Cheapflights users on 3/30. 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.
Fri 5/24:44 pmSDQ - PDX
2 stops23h 53mMultiple Airlines
Tue 5/131:37 pmPDX - SDQ
3 stops23h 52mMultiple Airlines
Deal found 3/30$488
This Mytrip deal was found by Cheapflights users on 4/1. 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 5/21:39 pmKIN - PDX
2 stops25h 58mSpirit Airlines
Thu 5/85:40 pmPDX - KIN
2 stops16h 49mSpirit Airlines
Deal found 4/1$500
This Mytrip deal was found by Cheapflights users on 4/1. 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 5/712:07 pmMBJ - PDX
2 stops30h 38mSpirit Airlines
Wed 5/145:40 pmPDX - MBJ
3 stops39h 22mSpirit Airlines
Deal found 4/1$515
This Mytrip deal was found by Cheapflights users on 4/1. 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 5/161:34 pmKIN - PDX
3 stops25h 08mMultiple Airlines
Fri 5/234:35 pmPDX - KIN
2 stops17h 54mMultiple Airlines
Deal found 4/1$553
This American Airlines deal was found by Cheapflights users on 4/1. 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 5/212:46 pmKIN - PDX
1 stop12h 42mAmerican Airlines
Thu 5/810:24 pmPDX - KIN
1 stop13h 01mAmerican Airlines
Deal found 4/1$571
This United Airlines deal was found by Cheapflights users on 4/1. 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 5/72:40 pmMBJ - PDX
1 stop10h 05mUnited Airlines
Wed 5/141:45 pmPDX - MBJ
2 stops21h 45mUnited Airlines
Deal found 4/1$571

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 2, 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

Wed 5/7

1:10 pm-8:36 pm

1 stop10h 26m

Portland

Mon 5/12

9:38 pm-8:33 pm

1 stop19h 55m

$369

San JuanBoise

SJU - BOI

SJUBOI

San Juan Luis Munoz Marin Intl

Thu 9/11

2:28 pm-10:43 pm

1 stop10h 15m

Boise Air Term. Gowen Fld

Tue 9/16

7:30 pm-4:18 pm

2 stops18h 48m

$405

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Wed 5/28

1:12 pm-11:15 pm

1 stop13h 03m

Portland

Sun 6/1

8:17 pm-12:45 pm

2 stops13h 28m

$416

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 5/15

1:33 am-12:42 pm

3 stops38h 09m

Portland

Fri 5/23

4:35 pm-7:07 pm

2 stops23h 32m

$437

Santo DomingoPortland

SDQ - PDX

SDQPDX

Santo Domingo Las Americas

Fri 5/2

4:44 pm-1:37 pm

2 stops23h 53m

Portland

Tue 5/13

5:40 pm-3:00 pm

2 stops18h 20m

$455

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Tue 5/6

1:05 am-12:39 pm

2 stops14h 34m

Portland

Mon 5/12

6:30 pm-1:45 pm

2 stops16h 15m

$459

Santo DomingoPortland

SDQ - PDX

SDQPDX

Santo Domingo Las Americas

Fri 5/2

4:44 pm-1:37 pm

2 stops23h 53m

Portland

Tue 5/13

1:37 pm-4:29 pm

3 stops23h 52m

$488

KingstonPortland

KIN - PDX

KINPDX

Kingston Norman Manley

Fri 5/2

1:39 pm-1:37 pm

2 stops25h 58m

Portland

Thu 5/8

5:40 pm-12:29 pm

2 stops16h 49m

$500

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Wed 5/7

12:07 pm-4:45 pm

2 stops30h 38m

Portland

Wed 5/14

5:40 pm-11:02 am

3 stops39h 22m

$515

KingstonPortland

KIN - PDX

KINPDX

Kingston Norman Manley

Fri 5/16

1:34 pm-12:42 pm

3 stops25h 08m

Portland

Fri 5/23

4:35 pm-12:29 pm

2 stops17h 54m

$553

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 53 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 $369). 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 April 2, 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.

Rainfall in Oregon by month

Plan your trip to Oregon by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Oregon ranges from 0.7 - 5.6 inches per month. November is typically the wettest month, when rainfall can reach 5.6 in. July is typically the driest time to visit Oregon when rainfall is around 0.7 in.

Temperature in Oregon by month

Plan your trip to Oregon by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Oregon, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 41.0 F).

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 2, 2025.
Alaska Airlines
8.0
Very good
9,820 reviews

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,820 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,272 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,898 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,615 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
JetBlue
7.3
Good
2,922 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 Spirit Airlines ($165), United Airlines ($185), and Delta ($203).

  • 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 $369). 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 6 airlines flying from Caribbean to Oregon

Discover the top 6 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 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$288Average$517FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$310Average$385FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$312Average$597FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$342Average$559FlexibilityNo cancel feeOn-time71%
DeltaCheapest$354Average$435FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$424Average$570FlexibilityNo cancel feeOn-time63%

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