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Caribbean Islands

$159+ Cheap flights from Oregon to Caribbean Islands

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 6/14. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheap flight deals from Oregon to Caribbean Islands

Keep the following information in mind while searching for Oregon to Caribbean Islands flight deals. Data was last updated May 1, 2025.

Round-trip from

$376
(Booking.com)

One-way from

$159
(Cheapflightsfares)

Popular in

March

Cheapest in

September

Average price

$482
From Oregon to Caribbean Islands
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One-way flight from Oregon to Caribbean Islands
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Highest demand for flights based on searches. 13% potential increase in price ($83 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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Find flight deals from Oregon to Caribbean Islands

Cheapest flights from Oregon to Caribbean Islands
Explore the most affordable flight options available from Oregon to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

This Booking.com deal was found by Cheapflights users on 4/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/41:37 pmPDX - STT
2 stops17h 20mSpirit Airlines
Wed 6/1110:52 amSTT - PDX
2 stops27h 25mSpirit Airlines
Deal found 4/29$376
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/167:00 amPDX - SJU
1 stop12h 42mDelta
Wed 10/11:13 pmSJU - PDX
1 stop13h 16mDelta
Deal found 4/30$379
This FlightHub deal was found by Cheapflights users on 4/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/261:37 pmPDX - SJU
2 stops18h 54mSpirit Airlines
Mon 6/21:59 amSJU - PDX
2 stops17h 46mSpirit Airlines
Deal found 4/30$380
This United Airlines deal was found by Cheapflights users on 4/29. 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 10/225:00 amPDX - SJU
1 stop9h 30mUnited Airlines
Sat 10/257:00 amSJU - PDX
2 stops16h 41mUnited Airlines
Deal found 4/29$397
This Expedia deal was found by Cheapflights users on 4/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/101:37 pmPDX - PUJ
2 stops21h 40mSpirit Airlines
Tue 6/173:23 pmPUJ - PDX
2 stops22h 54mSpirit Airlines
Deal found 4/30$413
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/187:45 pmBOI - SJU
2 stops15h 35mDelta
Sat 7/262:30 pmSJU - BOI
2 stops11h 29mDelta
Deal found 4/30$415
This Mytrip deal was found by Cheapflights users on 4/30. 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.
Sat 5/245:40 pmPDX - MBJ
2 stops15h 22mSpirit Airlines
Wed 5/2812:07 pmMBJ - PDX
2 stops26h 35mSpirit Airlines
Deal found 4/30$436
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/3010:24 pmPDX - SJU
1 stop11h 15mAmerican Airlines
Wed 6/41:10 pmSJU - PDX
2 stops13h 49mAmerican Airlines
Deal found 4/30$442
This CheapOair deal was found by Cheapflights users on 4/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/236:30 pmPDX - SJU
1 stop16h 17mMultiple Airlines
Mon 5/261:59 amSJU - PDX
2 stops17h 46mMultiple Airlines
Deal found 4/30$458
This Southwest deal was found by Cheapflights users on 4/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/106:10 amPDX - SJU
2 stops10h 35mSouthwest
Wed 9/1711:50 amSJU - PDX
2 stops13h 05mSouthwest
Deal found 4/30$460
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/119:38 pmPDX - NAS
1 stop13h 07mAmerican Airlines
Sat 5/177:45 amNAS - PDX
1 stop18h 26mAmerican Airlines
Deal found 4/30$465
This JetBlue deal was found by Cheapflights users on 4/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1311:35 pmPDX - SJU
1 stop13h 14mJetBlue
Mon 6/1612:55 pmSJU - PDX
1 stop12h 20mJetBlue
Deal found 4/29$474

Cheapflights Fare Finder

Customize your flight search to find flights from Oregon to Caribbean Islands 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 May 1, 2025.
Use the filters below to find and compare flights from Oregon to Caribbean Islands that are best for you.

Fly from

Oregon

Fly to

Caribbean Islands

Route

Depart

Return

Price

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Wed 6/4

1:37 pm-9:57 am

2 stops17h 20m

Saint Thomas Island Cyril E King

Wed 6/11

10:52 am-11:17 am

2 stops27h 25m

$376

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

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 5/26

1:37 pm-11:31 am

2 stops18h 54m

San Juan Luis Munoz Marin Intl

Mon 6/2

1:59 am-4:45 pm

2 stops17h 46m

$380

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 10/22

5:00 am-5:30 pm

1 stop9h 30m

San Juan Luis Munoz Marin Intl

Sat 10/25

7:00 am-8:41 pm

2 stops16h 41m

$397

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Tue 6/10

1:37 pm-2:17 pm

2 stops21h 40m

Punta Cana

Tue 6/17

3:23 pm-11:17 am

2 stops22h 54m

$413

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Fri 7/18

7:45 pm-1:20 pm

2 stops15h 35m

San Juan Luis Munoz Marin Intl

Sat 7/26

2:30 pm-11:59 pm

2 stops11h 29m

$415

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Sat 5/24

5:40 pm-11:02 am

2 stops15h 22m

Montego Bay Sangster Intl

Wed 5/28

12:07 pm-12:42 pm

2 stops26h 35m

$436

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 5/30

10:24 pm-12:39 pm

1 stop11h 15m

San Juan Luis Munoz Marin Intl

Wed 6/4

1:10 pm-11:59 pm

2 stops13h 49m

$442

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 5/23

6:30 pm-1:47 pm

1 stop16h 17m

San Juan Luis Munoz Marin Intl

Mon 5/26

1:59 am-4:45 pm

2 stops17h 46m

$458

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 9/10

6:10 am-7:45 pm

2 stops10h 35m

San Juan Luis Munoz Marin Intl

Wed 9/17

11:50 am-9:55 pm

2 stops13h 05m

$460

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 56 results
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Best time to book a flight from Oregon to Caribbean Islands

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

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

Currently, September is the cheapest month in which you can book a flight from Oregon to Caribbean Islands (average of $254). Flying from Oregon to Caribbean Islands 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 EPX?

Find hourly flight availability from Oregon to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 1, 2025.

When flying from Oregon to Caribbean Islands, 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 Caribbean Islands by month

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

In terms of precipitation, rainfall in Caribbean Islands 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 Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

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

If weather is an important factor for your trip to Caribbean Islands, 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 Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated May 1, 2025.
Read through reviews of airlines operating flights from Oregon to Caribbean Islands, such as Alaska Airlines, Southwest and Delta. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,968 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,968 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,294 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,934 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,924 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Related info for your journey

Find useful and relevant information for your journey from Oregon to Caribbean Islands. 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 Islands one-way?

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $159. Delta flights start at $190 while deals on Southwest start at $227 one-way.

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

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

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

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

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

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

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

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Alternative routes for Oregon to Caribbean Islands

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 Islands

Discover the top 9 airlines that operate flights from Oregon to Caribbean Islands. 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$202Average$696FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$223Average$306FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$245Average$373FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$250Average$591FlexibilityNo cancel feeOn-time75%
JetBlueCheapest$288Average$380FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$298Average$713FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$327Average$730FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$450Average$701FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$475Average$717FlexibilityNo cancel feeOn-time83%

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