HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$179+ 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 7/14. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Oregon to Caribbean Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 June 18, 2025.

Round-trip from

$375
(FlightHub)

One-way from

$179
(FlightHub)

Popular in

March

Cheapest in

September

Average price

$635
From Oregon to Caribbean Islands
Search Deals
One-way flight from Oregon to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($74 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
Search Deals

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 June 18, 2025.

This FlightHub deal was found by Cheapflights users on 6/17. 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 7/86:39 pmPDX - SJU
2 stops13h 53mSpirit Airlines
Tue 7/154:43 pmSJU - PDX
2 stops24h 32mSpirit Airlines
Deal found 6/17$375
This FlightHub deal was found by Cheapflights users on 6/18. 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 7/86:39 pmPDX - STT
2 stops14h 51mSpirit Airlines
Tue 7/151:25 pmSTT - PDX
2 stops22h 53mSpirit Airlines
Deal found 6/18$384
This Delta deal was found by Cheapflights users on 6/17. 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 9/1210:55 pmPDX - SJU
1 stop11h 15mDelta
Wed 9/177:00 amSJU - PDX
2 stops19h 51mDelta
Deal found 6/17$399
This Delta deal was found by Cheapflights users on 6/17. 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.
Sat 9/66:00 amBOI - SJU
2 stops14h 07mDelta
Sat 9/132:15 pmSJU - BOI
2 stops11h 23mDelta
Deal found 6/17$415
This FlightHub deal was found by Cheapflights users on 6/17. 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.
Sat 7/512:12 pmPDX - PUJ
2 stops22h 58mSpirit Airlines
Sat 7/121:00 pmPUJ - PDX
2 stops23h 18mSpirit Airlines
Deal found 6/17$444
This Mytrip deal was found by Cheapflights users on 6/16. 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.
Mon 7/219:22 amPDX - STT
3 stops26h 48mMultiple Airlines
Sun 7/2710:43 amSTT - PDX
2 stops25h 35mMultiple Airlines
Deal found 6/16$446
This Southwest deal was found by Cheapflights users on 6/17. 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 9/176:40 pmPDX - SJU
2 stops12h 35mSouthwest
Sun 9/215:05 amSJU - PDX
2 stops18h 35mSouthwest
Deal found 6/17$447
This FlightHub deal was found by Cheapflights users on 6/17. 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.
Sun 7/273:10 pmPDX - MBJ
2 stops17h 55mSpirit Airlines
Sat 8/212:10 pmMBJ - PDX
2 stops23h 08mSpirit Airlines
Deal found 6/17$450
This United Airlines deal was found by Cheapflights users on 6/15. 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.
Sun 9/216:31 pmEUG - SJU
2 stops16h 14mUnited Airlines
Sun 9/282:00 pmSJU - EUG
1 stop10h 05mUnited Airlines
Deal found 6/15$474
This Delta deal was found by Cheapflights users on 6/16. 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 9/235:30 pmEUG - SJU
2 stops15h 33mDelta
Mon 9/297:00 amSJU - EUG
2 stops19h 14mDelta
Deal found 6/16$475
This Mytrip deal was found by Cheapflights users on 6/17. 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 7/910:23 amPDX - SJU
2 stops22h 09mMultiple Airlines
Tue 7/151:21 amSJU - PDX
2 stops18h 55mMultiple Airlines
Deal found 6/17$476
This American Airlines deal was found by Cheapflights users on 6/17. 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 8/2711:12 pmPDX - SJU
1 stop20h 37mAmerican Airlines
Wed 9/36:10 amSJU - PDX
2 stops16h 13mAmerican Airlines
Deal found 6/17$482

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 June 18, 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

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 7/8

6:39 pm-11:32 am

2 stops13h 53m

San Juan Luis Munoz Marin Intl

Tue 7/15

4:43 pm-2:15 pm

2 stops24h 32m

$375

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Tue 7/8

6:39 pm-12:30 pm

2 stops14h 51m

Saint Thomas Island Cyril E King

Tue 7/15

1:25 pm-9:18 am

2 stops22h 53m

$384

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 9/12

10:55 pm-1:10 pm

1 stop11h 15m

San Juan Luis Munoz Marin Intl

Thu 9/18

7:00 am-11:51 pm

2 stops19h 51m

$399

BoiseSan Juan

BOI - SJU

BOISJU

Boise Air Term. Gowen Fld

Sat 9/6

6:00 am-10:07 pm

2 stops14h 07m

San Juan Luis Munoz Marin Intl

Sat 9/13

2:15 pm-11:38 pm

2 stops11h 23m

$415

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Sat 7/5

12:12 pm-2:10 pm

2 stops22h 58m

Punta Cana

Sat 7/12

1:00 pm-9:18 am

2 stops23h 18m

$444

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Mon 7/21

9:22 am-3:10 pm

3 stops26h 48m

Saint Thomas Island Cyril E King

Sun 7/27

10:43 am-9:18 am

2 stops25h 35m

$446

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 9/17

6:40 pm-10:15 am

2 stops12h 35m

San Juan Luis Munoz Marin Intl

Sun 9/21

5:05 am-8:40 pm

2 stops18h 35m

$447

PortlandMontego Bay

PDX - MBJ

PDXMBJ

Portland

Sun 7/27

3:10 pm-11:05 am

2 stops17h 55m

Montego Bay Sangster Intl

Sat 8/2

12:10 pm-9:18 am

2 stops23h 08m

$450

EugeneSan Juan

EUG - SJU

EUGSJU

Eugene

Sun 9/21

6:31 pm-1:45 pm

2 stops16h 14m

San Juan Luis Munoz Marin Intl

Sun 9/28

2:00 pm-9:05 pm

1 stop10h 05m

$474

EugeneSan Juan

EUG - SJU

EUGSJU

Eugene

Tue 9/23

5:30 pm-12:03 pm

2 stops15h 33m

San Juan Luis Munoz Marin Intl

Mon 9/29

7:00 am-11:14 pm

2 stops19h 14m

$475

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Showing 1-10 of 60 results
1
2
3
...
6

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 June is currently the most expensive (average of $339). 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 June 18, 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 June 18, 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
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Southwest
8.0
Very good
4,278 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Delta
8.0
Very good
7,964 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Copa Airlines
7.5
Good
1,455 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
United Airlines
7.4
Good
8,809 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.

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 $179. JetBlue flights start at $190 while deals on Delta start at $200 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 June is currently the most expensive (average of $339). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Oregon to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Cancún flights
Los Angeles to John F Kennedy Intl flights
Dallas/Fort Worth to LaGuardia flights
Newark to Fort Lauderdale flights
Los Angeles to Seattle flights
Dallas/Fort Worth to Seattle flights
John F Kennedy Intl to Miami flights
Los Angeles to Newark flights
LaGuardia to Fort Lauderdale flights
Newark to Cancún flights
John F Kennedy Intl to Seattle flights
Newark to O'Hare Intl flights
Newark to Miami flights
John F Kennedy Intl to O'Hare Intl flights
LaGuardia to Dallas/Fort Worth flights
Los Angeles to Honolulu flights
Newark to Seattle flights
LaGuardia to Miami flights
John F Kennedy Intl to Orlando flights
Dallas/Fort Worth to Cancún flights
LaGuardia to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
San Francisco to Seattle flights
Dallas/Fort Worth to John F Kennedy Intl flights
John F Kennedy Intl to Los Angeles flights
O'Hare Intl to Cancún flights
San Francisco to John F Kennedy Intl flights
Seattle to Los Angeles flights
Los Angeles to O'Hare Intl flights
John F Kennedy Intl to Fort Lauderdale flights
George Bush Intcntl to Cancún flights
Newark to Los Angeles flights
Newark to Orlando flights
Dallas/Fort Worth to Newark flights
John F Kennedy Intl to Las Vegas flights
John F Kennedy Intl to San Francisco flights
John F Kennedy Intl to Mexico City flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Seattle flights
San Francisco to Newark flights
Dallas/Fort Worth to Las Vegas flights
Fort Lauderdale to Newark flights
LaGuardia to Orlando flights
O'Hare Intl to LaGuardia flights
Los Angeles to LaGuardia flights
Fort Lauderdale to LaGuardia flights
Atlanta to John F Kennedy Intl flights
LaGuardia to Atlanta flights
Newark to San Francisco flights
Atlanta to Las Vegas flights

Top 8 airlines flying from Oregon to Caribbean Islands

Discover the top 8 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 June 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$380FlexibilityNo cancel feeOn-time62%
DeltaCheapest$202Average$696FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$251Average$363FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$306Average$698FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$328Average$719FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$450Average$713FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$454Average$599FlexibilityNo cancel feeOn-time75%
Sun Country AirCheapest$475Average$737FlexibilityNo cancel feeOn-time83%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.