Caribbean

$124+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Jan 26 — Feb 21
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Cheap flight deals from Oregon to Caribbean

Discover tips and strategies to find the most affordable flight options for your journey from Oregon (USOR) to Caribbean (0CB). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$261
(FlightHub)

One-way from

$142
(CheapOair)
From Oregon to Caribbean
One-way flight from Oregon to Caribbean

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 January 21, 2025.

This FlightHub deal was found by Cheapflights users on 1/21. 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 2/257:41 pmBOI - SJU
2 stops18h 20mSpirit Airlines
Tue 3/45:56 pmSJU - BOI
2 stops21h 36mSpirit Airlines
Deal found 1/21$261
This CheapOair deal was found by Cheapflights users on 1/20. 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.
Tue 2/258:28 pmPDX - STT
2 stops34h 18mSpirit Airlines
Mon 3/311:41 amSTT - PDX
2 stops35h 50mSpirit Airlines
Deal found 1/20$296
This Mytrip deal was found by Cheapflights users on 1/20. 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 3/28:28 pmPDX - SJU
3 stops40h 52mSpirit Airlines
Fri 3/74:12 pmSJU - PDX
2 stops30h 25mSpirit Airlines
Deal found 1/20$339
This American Airlines deal was found by Cheapflights users on 1/20. 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 4/711:59 pmPDX - SJU
2 stops14h 11mAmerican Airlines
Wed 4/166:21 amSJU - PDX
1 stop19h 51mAmerican Airlines
Deal found 1/20$359
This Orbitz deal was found by Cheapflights users on 1/19. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/41:23 pmBOI - SJU
1 stop12h 46mMultiple Airlines
Tue 3/1112:05 pmSJU - BOI
2 stops26h 27mMultiple Airlines
Deal found 1/19$377
This Delta deal was found by Cheapflights users on 1/21. 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.
Mon 4/147:55 pmBOI - SJU
2 stops13h 55mDelta
Thu 4/242:35 pmSJU - BOI
1 stop10h 06mDelta
Deal found 1/21$395
This CheapOair deal was found by Cheapflights users on 1/21. 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.
Mon 4/76:40 amPDX - PUJ
2 stops25h 49mFrontier
Thu 4/101:04 pmPUJ - PDX
2 stops22h 07mFrontier
Deal found 1/21$403
This American Airlines deal was found by Cheapflights users on 1/21. 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 2/267:05 amBOI - SJU
2 stops13h 50mAmerican Airlines
Tue 3/46:29 pmSJU - BOI
2 stops21h 01mAmerican Airlines
Deal found 1/21$420
This United Airlines deal was found by Cheapflights users on 1/21. 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 3/46:58 pmBOI - SJU
2 stops15h 19mUnited Airlines
Mon 3/101:05 amSJU - BOI
2 stops14h 23mUnited Airlines
Deal found 1/21$424
This Delta deal was found by Cheapflights users on 1/21. 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.
Sun 2/237:35 pmPDX - SJU
2 stops17h 21mDelta
Thu 2/272:11 pmSJU - PDX
2 stops13h 47mDelta
Deal found 1/21$425
This Mytrip deal was found by Cheapflights users on 1/20. 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 2/219:18 pmPDX - SDQ
2 stops37h 22mFrontier
Tue 3/44:00 pmSDQ - PDX
2 stops20h 00mFrontier
Deal found 1/20$433
This American Airlines deal was found by Cheapflights users on 1/19. 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 2/2410:55 pmPDX - NAS
1 stop10h 05mAmerican Airlines
Tue 3/48:03 amNAS - PDX
1 stop18h 55mAmerican Airlines
Deal found 1/19$435

Find flights from Oregon to Caribbean within your budget

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Tue 2/25

7:41 pm-5:01 pm

2 stops18h 20m

San Juan Luis Munoz Marin Intl

Tue 3/4

5:56 pm-12:32 pm

2 stops21h 36m

$261

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Tue 2/25

8:28 pm-10:46 am

2 stops34h 18m

Saint Thomas Island Cyril E King

Mon 3/3

11:41 am-7:31 pm

2 stops35h 50m

$296

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 3/2

8:28 pm-5:20 pm

3 stops40h 52m

San Juan Luis Munoz Marin Intl

Fri 3/7

4:12 pm-6:37 pm

2 stops30h 25m

$339

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 4/7

11:59 pm-2:27 pm

1 stop11h 28m

San Juan Luis Munoz Marin Intl

Wed 4/16

6:21 am-11:12 pm

1 stop19h 51m

$359

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Mon 4/14

7:55 pm-11:50 am

2 stops13h 55m

San Juan Luis Munoz Marin Intl

Thu 4/24

2:35 pm-10:41 pm

1 stop10h 06m

$395

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Mon 4/7

6:40 am-11:29 am

2 stops25h 49m

Punta Cana

Thu 4/10

1:04 pm-8:11 am

2 stops22h 07m

$403

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Wed 2/26

7:05 am-11:55 pm

2 stops13h 50m

San Juan Luis Munoz Marin Intl

Tue 3/4

6:29 pm-12:30 pm

2 stops21h 01m

$420

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 2/23

12:59 am-4:27 pm

1 stop11h 28m

San Juan Luis Munoz Marin Intl

Fri 3/7

2:11 pm-11:58 pm

2 stops13h 47m

$425

PortlandSanto Domingo

PDX - SDQ

PDXSDQ

Portland

Fri 2/21

9:18 pm-2:40 pm

2 stops37h 22m

Santo Domingo Las Americas

Tue 3/4

4:00 pm-8:00 am

2 stops20h 00m

$433

PortlandNassau

PDX - NAS

PDXNAS

Portland

Mon 2/24

10:55 pm-12:00 pm

1 stop10h 05m

Nassau Intl

Tue 3/4

8:03 am-11:58 pm

1 stop18h 55m

$435

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 58 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.

Travel insights for flights from Oregon to Caribbean

Get recent, data-driven insights about flights from Oregon to Caribbean including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $378). 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 January 21, 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 January 21, 2025.
8.1
Very good
4,662 reviews

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.1
Very good
4,662 reviews
8.1
Very good
4,662 reviews

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
9,706 reviews
8.1
Very good
4,662 reviews

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
8,521 reviews
8.1
Very good
4,662 reviews

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.7
Good
1,662 reviews
8.1
Very good
4,662 reviews

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.5
Good
1,858 reviews
8.1
Very good
4,662 reviews

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $142. Users have also found prices from $180 and $213 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 March is currently the most expensive (average of $378). 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.

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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$348FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$225Average$359FlexibilityNo cancel feeOn-time65%
Alaska AirlinesCheapest$236Average$1,008FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$281Average$710FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$288Average$513FlexibilityNo cancel feeOn-time62%
DeltaCheapest$305Average$711FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$336Average$741FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$474Average$669FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$475Average$717FlexibilityNo cancel feeOn-time83%
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