HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$174+ Cheap flights from Caribbean Islands to Portland (PDX)

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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Caribbean Islands to Portland 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 Caribbean Islands to Portland

Keep the following information in mind while searching for Caribbean Islands to Portland flight deals. Data was last updated February 20, 2025.

Round-trip from

$191
(Trip.com)

One-way from

$174
(Booking.com)
From Caribbean Islands to Portland
Search Deals
One-way flight from Caribbean Islands to Portland
Search Deals

Find flight deals from Caribbean Islands to Portland

Cheapest flights from Caribbean Islands to Portland
Explore the most affordable flight options available from Caribbean Islands to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This Trip.com deal was found by Cheapflights users on 2/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/66:45 amSJU - PDX
2 stops29h 55mFrontier
Mon 3/109:18 pmPDX - SJU
2 stops43h 58mFrontier
Deal found 2/19$191
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/66:00 amSJU - PDX
2 stops35h 38mSpirit Airlines
Mon 3/102:33 pmPDX - SJU
3 stops39h 59mSpirit Airlines
Deal found 2/19$293
This American Airlines deal was found by Cheapflights users on 2/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/111:45 amSJU - PDX
1 stop11h 50mAmerican Airlines
Mon 5/511:59 pmPDX - SJU
2 stops11h 41mAmerican Airlines
Deal found 2/18$369
This Priceline deal was found by Cheapflights users on 2/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/94:30 pmSDQ - PDX
2 stops18h 52mSpirit Airlines
Tue 4/152:33 pmPDX - SDQ
2 stops22h 02mSpirit Airlines
Deal found 2/19$424
This United Airlines deal was found by Cheapflights users on 2/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/181:40 pmSJU - PDX
2 stops13h 50mUnited Airlines
Sun 4/2711:59 pmPDX - SJU
1 stop11h 45mUnited Airlines
Deal found 2/19$443
This eDestinos deal was found by Cheapflights users on 2/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/264:05 pmSJU - PDX
1 stop28h 19mMultiple Airlines
Sat 5/36:20 amPDX - SJU
3 stops41h 31mMultiple Airlines
Deal found 2/19$450
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/512:43 pmSJU - PDX
1 stop13h 44mDelta
Fri 9/1210:55 pmPDX - SJU
1 stop11h 15mDelta
Deal found 2/20$465
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/94:30 pmSDQ - PDX
2 stops18h 52mMultiple Airlines
Mon 4/149:27 amPDX - SDQ
3 stops33h 18mMultiple Airlines
Deal found 2/19$495
This Mytrip deal was found by Cheapflights users on 2/20. 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 4/61:36 pmKIN - PDX
2 stops22h 44mMultiple Airlines
Sun 4/1311:59 pmPDX - KIN
2 stops18h 36mMultiple Airlines
Deal found 2/20$551
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/611:25 amGCM - PDX
2 stops27h 00mMultiple Airlines
Sun 4/1310:06 amPDX - GCM
1 stop28h 04mMultiple Airlines
Deal found 2/20$598
This Southwest deal was found by Cheapflights users on 2/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/265:00 amSJU - PDX
2 stops11h 40mSouthwest
Mon 6/306:55 pmPDX - SJU
2 stops12h 45mSouthwest
Deal found 2/20$618
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/68:00 amKIN - PDX
1 stop12h 02mDelta
Sun 4/136:15 amPDX - KIN
1 stop10h 38mDelta
Deal found 2/20$626

Find flights from Caribbean Islands to Portland within your budget

Customize your flight search to find flights from Caribbean Islands to Portland 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 February 20, 2025.

Fly from

Caribbean Islands

Fly to

Portland

Route

Depart

Return

Price

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 3/6

6:45 am-8:40 am

2 stops29h 55m

Portland

Mon 3/10

9:18 pm-8:16 pm

2 stops43h 58m

$191

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 3/6

6:00 am-1:38 pm

2 stops35h 38m

Portland

Mon 3/10

2:33 pm-9:32 am

3 stops39h 59m

$293

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 5/1

11:45 am-8:35 pm

1 stop11h 50m

Portland

Mon 5/5

11:59 pm-2:40 pm

2 stops11h 41m

$369

Santo DomingoPortland

SDQ - PDX

SDQPDX

Santo Domingo Las Americas

Wed 4/9

4:30 pm-8:22 am

2 stops18h 52m

Portland

Tue 4/15

2:33 pm-3:35 pm

2 stops22h 02m

$424

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Fri 4/18

1:40 pm-12:30 am

2 stops13h 50m

Portland

Sun 4/27

11:59 pm-2:44 pm

1 stop11h 45m

$443

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Sat 4/26

4:05 pm-5:24 pm

1 stop28h 19m

Portland

Sat 5/3

6:20 am-2:51 am

3 stops41h 31m

$450

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Sat 4/26

6:35 am-10:18 pm

2 stops18h 43m

Portland

Fri 5/2

12:50 am-2:02 pm

1 stop10h 12m

$465

Santo DomingoPortland

SDQ - PDX

SDQPDX

Santo Domingo Las Americas

Wed 4/9

4:30 pm-8:22 am

2 stops18h 52m

Portland

Mon 4/14

9:27 am-9:45 pm

3 stops33h 18m

$495

KingstonPortland

KIN - PDX

KINPDX

Kingston Norman Manley

Sun 4/6

1:36 pm-10:20 am

2 stops22h 44m

Portland

Sun 4/13

11:59 pm-8:35 pm

2 stops18h 36m

$551

George TownPortland

GCM - PDX

GCMPDX

George Town Owen Roberts Intl

Sun 4/6

11:25 am-12:25 pm

2 stops27h 00m

Portland

Sun 4/13

10:06 am-4:10 pm

1 stop28h 04m

$598

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 37 results
1
2
3
4

Best time to book a flight from Caribbean Islands to Portland

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

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

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

Currently, November is the cheapest month in which you can book a flight from Caribbean Islands to Portland (average of $277). Flying from Caribbean Islands to Portland in March is currently the most expensive (average of $376). 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 EPX to PDX?

Find hourly flight availability from Caribbean Islands to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 20, 2025.

When flying from Caribbean Islands to Portland, 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 Portland by month

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

In terms of precipitation, rainfall in Portland 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 Portland when rainfall is around 0.7 in.

Temperature in Portland by month

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

If weather is an important factor for your trip to Portland, 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 Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated February 20, 2025.
See what other customers who have flown with Southwest, Alaska Airlines and Delta from Caribbean Islands to Portland have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Caribbean Islands to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Portland from Caribbean Islands?

    Portland (PDX) is the airport you will fly into if you book a flight from Caribbean Islands to Portland. It is only a 6.0 mi journey from Portland (PDX) to Portland’s city center.

  • What are the cheapest airlines to fly from Caribbean Islands to Portland one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $174. However, be on the lookout for offers from American Airlines and Delta, as they are both options that can get you from Caribbean Islands to Portland for a low price.

  • What are the most popular routes from Caribbean Islands to Portland?

    Most travelers choose San Juan Luis Munoz Marin Intl - Portland, Santo Domingo Las Americas - Portland or George Town Owen Roberts Intl - Portland when deciding on the best route from Caribbean Islands to Portland.

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

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

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

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

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

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

    Currently, November is the cheapest month in which you can book a flight from Caribbean Islands to Portland (average of $277). Flying from Caribbean Islands to Portland in March is currently the most expensive (average of $376). 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

Traveling to a place near Caribbean Islands?

Book flights to Caribbean Islands if you plan to visit one of these locations
Seaside
Lincoln City
Beaverton
McMinnville
Lake Oswego
Hillsboro
Vancouver
Gresham
Long Beach
Cannon Beach
Tigard
Astoria
Hood River
Woodburn
Depoe Bay
Pacific City
Stevenson
Troutdale
Longview
Wilsonville

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 Caribbean Islands to Portland

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to Portland flights
John F Kennedy Intl to Portland flights
Dallas/Fort Worth to Portland flights
Newark to Portland flights
O'Hare Intl to Portland flights
Minneapolis to Portland flights
Burbank to Portland flights
Ontario to Portland flights
San Francisco to Portland flights
Santa Ana to Portland flights
Denver to Portland flights
Sky Harbor Intl to Portland flights
Boston to Portland flights
Dulles Intl to Portland flights
San Diego to Portland flights
Reagan-National to Portland flights
LaGuardia to Portland flights
Orlando to Portland flights
Austin to Portland flights
Oakland to Portland flights
Hobby to Portland flights
Atlanta to Portland flights
San Jose to Portland flights
Midway to Portland flights
Salt Lake City to Portland flights
George Bush Intcntl to Portland flights
Los Angeles to Boise flights
San Francisco to Redmond flights
Seattle to Boise flights
Baltimore to Portland flights
Detroit to Portland flights
Kansas City to Portland flights
Sacramento to Portland flights
San Francisco to Eugene flights
Philadelphia to Portland flights
O'Hare Intl to Boise flights
Los Angeles to Redmond flights
Charlotte to Portland flights
Denver to Boise flights
Love Field to Portland flights
Nashville to Portland flights
Las Vegas to Portland flights
Dallas/Fort Worth to Boise flights
Burbank to Boise flights
Minneapolis to Boise flights
Honolulu to Portland flights
Los Angeles to Eugene flights
Sacramento to Boise flights
Sky Harbor Intl to Boise flights
Reno to Portland flights

Top 5 airlines flying from Caribbean Islands to Portland

Discover the top 5 airlines that operate flights from Caribbean Islands to Portland. 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$288Average$517FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$308Average$597FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$310Average$385FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$342Average$562FlexibilityNo cancel feeOn-time71%
DeltaCheapest$354Average$431FlexibilityNo cancel feeOn-timeN/A
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.