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Caribbean

$162+ Cheap flights from Oregon to Caribbean

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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Apr 7 — Apr 141
Mon 4/7
Mon 4/14
1 adult, Economy
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Cheap flight deals from Oregon to Caribbean

Keep the following information in mind while searching for Oregon to Caribbean flight deals. Data was last updated April 2, 2025.

Round-trip from

$369
(American Airlines)

One-way from

$162
(FlightHub)

Popular in

March

Cheapest in

September

Average price

$515
From Oregon to Caribbean
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One-way flight from Oregon to Caribbean
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Highest demand for flights based on searches. 11% potential increase in price ($75 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($22 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 Oregon to Caribbean

Cheapest flights from Oregon to Caribbean
Explore the most affordable flight options available from Oregon to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 2, 2025.

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 4/1110:25 amPDX - SJU
2 stops30h 15mSpirit Airlines
Tue 4/225:10 pmSJU - PDX
2 stops23h 27mSpirit Airlines
Deal found 4/1$353
This American Airlines deal was found by Cheapflights users on 4/2. 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.
Sat 4/2611:52 pmPDX - SJU
2 stops11h 53mAmerican Airlines
Thu 5/16:21 amSJU - PDX
1 stop20h 07mAmerican Airlines
Deal found 4/2$369
This Delta deal was found by Cheapflights users on 4/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/27:00 amPDX - SJU
1 stop12h 50mDelta
Fri 12/123:25 pmSJU - PDX
1 stop10h 29mDelta
Deal found 4/2$379
This FlightHub deal was found by Cheapflights users on 3/31. 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.
Tue 5/67:01 pmPDX - STT
2 stops11h 56mSpirit Airlines
Sat 5/103:49 pmSTT - PDX
2 stops27h 56mSpirit Airlines
Deal found 3/31$385
This United Airlines deal was found by Cheapflights users on 4/2. 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.
Thu 12/410:56 pmPDX - SJU
1 stop11h 44mUnited Airlines
Tue 12/92:05 amSJU - PDX
2 stops13h 30mUnited Airlines
Deal found 4/2$394
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.
Sun 4/1311:59 pmPDX - SJU
2 stops14h 34mMultiple Airlines
Sat 4/1912:54 amSJU - PDX
2 stops35h 18mMultiple Airlines
Deal found 4/1$397
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/71:37 pmPDX - PUJ
2 stops21h 40mSpirit Airlines
Fri 5/163:22 pmPUJ - PDX
2 stops24h 20mSpirit Airlines
Deal found 4/1$434
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 4/307:01 pmPDX - KIN
2 stops15h 30mSpirit Airlines
Wed 5/71:34 pmKIN - PDX
2 stops29h 11mSpirit Airlines
Deal found 4/1$436
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.
Mon 9/111:59 pmPDX - AUA
2 stops12h 46mAmerican Airlines
Mon 9/154:45 pmAUA - PDX
2 stops20h 45mAmerican Airlines
Deal found 4/1$441
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.
Fri 5/26:30 pmPDX - NAS
2 stops16h 20mUnited Airlines
Thu 5/85:00 pmNAS - PDX
1 stop8h 45mUnited Airlines
Deal found 4/1$465
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.
Tue 4/227:59 pmPDX - NAS
2 stops14h 45mDelta
Tue 4/293:09 pmNAS - PDX
2 stops11h 47mDelta
Deal found 4/1$469
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/159:30 pmPDX - NAS
1 stop19h 29mAlaska Airlines
Sat 5/249:00 amNAS - PDX
1 stop29h 52mAlaska Airlines
Deal found 4/1$472

Cheapflights Fare Finder

Customize your flight search to find flights from Oregon to Caribbean 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 Oregon to Caribbean that are best for you.

Fly from

Oregon

Fly to

Caribbean

Route

Depart

Return

Price

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 4/26

11:52 pm-2:45 pm

2 stops11h 53m

San Juan Luis Munoz Marin Intl

Thu 5/1

6:21 am-11:28 pm

1 stop20h 07m

$369

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 5/11

1:37 pm-12:44 pm

3 stops44h 07m

San Juan Luis Munoz Marin Intl

Thu 5/15

1:33 am-12:42 pm

3 stops38h 09m

$373

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 9/16

7:00 am-10:42 pm

1 stop12h 42m

San Juan Luis Munoz Marin Intl

Wed 10/1

1:13 pm-11:29 pm

1 stop13h 16m

$379

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Tue 5/6

7:01 pm-9:57 am

2 stops11h 56m

Saint Thomas Island Cyril E King

Sat 5/10

3:49 pm-4:45 pm

2 stops27h 56m

$385

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 4/13

11:59 pm-5:33 pm

2 stops14h 34m

San Juan Luis Munoz Marin Intl

Sat 4/19

12:54 am-9:12 am

2 stops35h 18m

$397

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Wed 5/7

1:37 pm-2:17 pm

2 stops21h 40m

Punta Cana

Fri 5/16

3:22 pm-12:42 pm

2 stops24h 20m

$434

PortlandKingston

PDX - KIN

PDXKIN

Portland

Wed 4/30

7:01 pm-12:31 pm

2 stops15h 30m

Kingston Norman Manley

Wed 5/7

1:34 pm-4:45 pm

2 stops29h 11m

$436

PortlandOranjestad

PDX - AUA

PDXAUA

Portland

Mon 9/1

11:59 pm-3:45 pm

2 stops12h 46m

Oranjestad Reina Beatrix

Mon 9/15

4:45 pm-10:30 am

2 stops20h 45m

$441

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 9/16

7:41 pm-1:45 pm

2 stops15h 04m

San Juan Luis Munoz Marin Intl

Tue 9/30

1:05 am-11:35 am

2 stops13h 30m

$459

PortlandNassau

PDX - NAS

PDXNAS

Portland

Fri 5/2

6:30 pm-1:50 pm

2 stops16h 20m

Nassau Intl

Thu 5/8

5:00 pm-10:45 pm

1 stop8h 45m

$465

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 55 results
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Best time to book a flight from Oregon to Caribbean

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

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

Currently, September is the cheapest month in which you can book a flight from Oregon to Caribbean (average of $254). Flying from Oregon to Caribbean in December is currently the most expensive (average of $336). 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 OR to CB?

Find hourly flight availability from Oregon to Caribbean. 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.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oregon to Caribbean as you normally would.

Rainfall in Caribbean by month

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

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

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

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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 Caribbean. Reviews last updated April 2, 2025.
Alaska Airlines
8.0
Very good
9,823 reviews

Boarding

8.2

Crew

8.5

Food

7.1

Comfort

7.9

Overall

8.0

Entertainment

7.1

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
9,823 reviews
Alaska Airlines
8.0
Very good
9,823 reviews

Boarding

8.2

Crew

8.5

Food

7.1

Comfort

7.9

Overall

8.0

Entertainment

7.1

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
4,275 reviews
Alaska Airlines
8.0
Very good
9,823 reviews

Boarding

8.2

Crew

8.5

Food

7.1

Comfort

7.9

Overall

8.0

Entertainment

7.1

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
7,899 reviews
Alaska Airlines
8.0
Very good
9,823 reviews

Boarding

8.2

Crew

8.5

Food

7.1

Comfort

7.9

Overall

8.0

Entertainment

7.1

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
LATAM Airlines
7.5
Good
1,754 reviews
Alaska Airlines
8.0
Very good
9,823 reviews

Boarding

8.2

Crew

8.5

Food

7.1

Comfort

7.9

Overall

8.0

Entertainment

7.1

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
9,823 reviews

Boarding

8.2

Crew

8.5

Food

7.1

Comfort

7.9

Overall

8.0

Entertainment

7.1

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 Oregon to Caribbean. 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 Oregon to Caribbean one-way?

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $162. Users have also found prices from $185 and $190 on American Airlines and Delta, respectively.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Oregon to Caribbean (average of $254). Flying from Oregon to Caribbean in December is currently the most expensive (average of $336). 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 Oregon to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 9 airlines flying from Oregon to Caribbean

Discover the top 9 airlines that operate flights from Oregon to Caribbean. 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
FrontierCheapest$145Average$363FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$242Average$586FlexibilityNo cancel feeOn-time75%
Spirit AirlinesCheapest$245Average$362FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$288Average$392FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$298Average$734FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$327Average$743FlexibilityNo cancel feeOn-time71%
DeltaCheapest$356Average$729FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$450Average$714FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$475Average$717FlexibilityNo cancel feeOn-time83%

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