HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$186+ Cheap flights from Caribbean 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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Caribbean 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 to Portland

Keep the following information in mind while searching for Caribbean to Portland flight deals. Data was last updated September 17, 2025.

Round-trip from

$419
(Delta)

One-way from

$186
(Kiwi.com)

Popular in

November

Cheapest in

February

Average price

$479
From Caribbean to Portland
Search Deals
One-way flight from Caribbean to Portland
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($65 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find flight deals from Caribbean to Portland

Cheapest flights from Caribbean to Portland
Explore the most affordable flight options available from Caribbean to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/283:00 pmSJU - PDX
1 stop11h 06mAmerican Airlines
Tue 11/410:45 pmPDX - SJU
1 stop10h 58mAmerican Airlines
Deal found 9/15$419
This Southwest deal was found by Cheapflights users on 9/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/305:50 amSJU - PDX
2 stops14h 30mSouthwest
Tue 11/48:00 amPDX - SJU
2 stops12h 35mSouthwest
Deal found 9/16$450
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/287:05 amSJU - PDX
2 stops12h 59mAmerican Airlines
Tue 11/115:42 pmPDX - SJU
2 stops14h 23mAmerican Airlines
Deal found 9/15$457
This Sun Country Air deal was found by Cheapflights users on 9/15. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/219:00 amSJU - PDX
1 stop11h 30mSun Country Air
Fri 9/266:24 pmPDX - SJU
1 stop17h 47mSun Country Air
Deal found 9/15$459
This eDestinos deal was found by Cheapflights users on 9/15. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/61:59 amSJU - PDX
3 stops36h 49mMultiple Airlines
Sat 10/115:38 pmPDX - SJU
2 stops18h 46mMultiple Airlines
Deal found 9/15$464
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/229:07 amSJU - PDX
2 stops18h 05mFrontier
Sat 9/278:02 amPDX - SJU
2 stops22h 50mFrontier
Deal found 9/15$470
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/71:06 pmSJU - PDX
2 stops13h 51mDelta
Sat 10/117:12 amPDX - SJU
1 stop13h 44mDelta
Deal found 9/15$482
This American Airlines deal was found by Cheapflights users on 9/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/113:00 pmSJU - PDX
1 stop11h 06mAmerican Airlines
Tue 10/1411:59 pmPDX - SJU
2 stops12h 55mAmerican Airlines
Deal found 9/16$492
This Mytrip deal was found by Cheapflights users on 9/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/16:44 amSJU - PDX
2 stops31h 27mMultiple Airlines
Sun 10/56:16 pmPDX - SJU
2 stops29h 35mMultiple Airlines
Deal found 9/15$493
This American Airlines deal was found by Cheapflights users on 9/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/143:00 pmSJU - PDX
1 stop21h 31mAmerican Airlines
Wed 10/225:05 amPDX - SJU
2 stops14h 05mAmerican Airlines
Deal found 9/16$495
This Delta deal was found by Cheapflights users on 9/14. 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.
Thu 10/301:32 pmMBJ - PDX
1 stop10h 36mDelta
Thu 11/63:19 pmPDX - MBJ
2 stops18h 04mDelta
Deal found 9/14$533
This United Airlines deal was found by Cheapflights users on 9/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/12:36 pmMBJ - PDX
2 stops22h 02mUnited Airlines
Sat 11/87:38 pmPDX - MBJ
2 stops15h 27mUnited Airlines
Deal found 9/17$541

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean 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 September 17, 2025.
Use the filters below to find and compare flights from Caribbean to Portland that are best for you.

Fly from

Caribbean

Fly to

Portland

Route

Depart

Return

Price

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Tue 10/7

1:06 pm-11:57 pm

2 stops13h 51m

Portland

Sat 10/18

7:12 am-11:56 pm

1 stop13h 44m

$419

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 2/26

7:30 am-8:47 pm

2 stops17h 17m

Portland

Mon 3/2

9:45 pm-1:00 pm

1 stop11h 15m

$419

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 10/30

12:46 pm-10:08 pm

1 stop12h 22m

Portland

Tue 11/4

7:12 am-12:56 am

1 stop13h 44m

$419

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 10/9

1:06 pm-11:57 pm

2 stops13h 51m

Portland

Fri 10/17

12:40 am-4:25 pm

2 stops12h 45m

$482

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Tue 10/28

7:00 am-10:27 pm

2 stops18h 27m

Portland

Mon 11/10

12:35 am-5:20 pm

2 stops12h 45m

$482

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Thu 10/30

1:32 pm-10:08 pm

1 stop10h 36m

Portland

Thu 11/6

3:19 pm-12:23 pm

2 stops18h 04m

$533

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Sat 11/1

2:20 pm-11:58 am

3 stops23h 38m

Portland

Sat 11/8

7:38 pm-2:05 pm

2 stops15h 27m

$541

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Thu 10/30

1:00 pm-11:08 pm

1 stop12h 08m

Portland

Thu 11/6

10:45 pm-2:12 pm

1 stop12h 27m

$542

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Thu 10/30

1:48 pm-9:38 am

2 stops21h 50m

Portland

Thu 11/6

7:10 pm-2:05 pm

2 stops39h 55m

$542

Punta CanaPortland

PUJ - PDX

PUJPDX

Punta Cana

Thu 2/19

2:05 pm-9:18 pm

1 stop11h 13m

Portland

Sun 2/22

10:56 pm-1:49 pm

1 stop10h 53m

$542

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 40 results
1
2
3
4

Best time to book a flight from Caribbean to Portland

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

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

Currently, November is the cheapest month in which you can book a flight from Caribbean to Portland (average of $277). Flying from Caribbean to Portland in March is currently the most expensive (average of $368). 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 CB to PDX?

Find hourly flight availability from Caribbean 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 September 17, 2025.

When flying from Caribbean 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.

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 September 17, 2025.
Read through reviews of airlines operating flights from Caribbean to Portland, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,961 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Caribbean 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?

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

  • How long is the flight from Caribbean to Portland?

    Departing from Caribbean to Portland will take you 12h 08m. The distance between Caribbean and Portland is about 3155 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    One-way options have recently been found by users for as low as $210 on American Airlines. Other airlines that offer cheap prices include United Airlines from $210 and Air Canada from $297 one-way.

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

    When deciding which route to take from Caribbean to Portland consider San Juan Luis Munoz Marin Intl - Portland, Santo Domingo Las Americas - Portland or Kingston Norman Manley - Portland as they are the most popular.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Caribbean 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 to Portland?

    Currently, November is the cheapest month in which you can book a flight from Caribbean to Portland (average of $277). Flying from Caribbean to Portland in March is currently the most expensive (average of $368). 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 Portland?

Book flights to Portland if you plan to visit one of these locations
Vancouver
Seaside
Beaverton
Clackamas
McMinnville
Lake Oswego
Hillsboro
Cannon Beach
Long Beach
Longview
Lincoln City
Tigard
Depoe Bay
Stevenson
Wilsonville
Pacific City
Tillamook
Troutdale
Gresham
Silverton

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 to Portland

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

Top 4 airlines flying from Caribbean to Portland

Discover the top 4 airlines that operate flights from Caribbean 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$248Average$512FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$353Average$589FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$406Average$587FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$424Average$565FlexibilityNo cancel feeOn-time63%

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.