HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$200+ 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 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$399
(Delta)

One-way from

$200
(Delta)

Popular in

November

Cheapest in

February

Average price

$565
From Caribbean to Portland
Search Deals
One-way flight from Caribbean to Portland
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($52 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 29, 2025.

This Delta deal was found by Cheapflights users on 7/28. 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 10/281:10 pmSJU - PDX
1 stop13h 19mDelta
Mon 11/312:50 amPDX - SJU
2 stops12h 35mDelta
Deal found 7/28$399
This American Airlines deal was found by Cheapflights users on 7/27. 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 10/167:10 amSJU - PDX
1 stop16h 52mAmerican Airlines
Tue 10/2111:59 pmPDX - SJU
1 stop11h 26mAmerican Airlines
Deal found 7/27$408
This Mytrip deal was found by Cheapflights users on 7/27. 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 9/151:59 amSJU - PDX
3 stops20h 05mSpirit Airlines
Mon 9/228:04 pmPDX - SJU
3 stops25h 40mSpirit Airlines
Deal found 7/27$411
This Mytrip deal was found by Cheapflights users on 7/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1111:59 amSJU - PDX
3 stops26h 13mMultiple Airlines
Thu 9/188:04 pmPDX - SJU
3 stops25h 40mMultiple Airlines
Deal found 7/29$434
This United Airlines deal was found by Cheapflights users on 7/28. 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.
Thu 9/1112:52 pmMBJ - PDX
2 stops35h 50mUnited Airlines
Thu 9/186:27 pmPDX - MBJ
2 stops41h 03mUnited Airlines
Deal found 7/28$467
This United Airlines deal was found by Cheapflights users on 7/28. 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 9/191:05 amSJU - PDX
1 stop11h 18mUnited Airlines
Fri 10/35:00 amPDX - SJU
1 stop9h 30mUnited Airlines
Deal found 7/28$489
This Trip.com deal was found by Cheapflights users on 7/27. 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.
Wed 9/1012:08 pmKIN - PDX
2 stops14h 07mMultiple Airlines
Wed 9/176:05 amPDX - KIN
2 stops26h 57mMultiple Airlines
Deal found 7/27$504
This Mytrip deal was found by Cheapflights users on 7/27. 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 9/1012:08 pmKIN - PDX
3 stops32h 56mSpirit Airlines
Wed 9/1712:07 pmPDX - KIN
3 stops20h 55mSpirit Airlines
Deal found 7/27$582
This Mytrip deal was found by Cheapflights users on 7/28. 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.
Tue 8/2612:19 pmMBJ - PDX
3 stops32h 38mSpirit Airlines
Wed 9/37:52 pmPDX - MBJ
3 stops37h 13mSpirit Airlines
Deal found 7/28$582
This American Airlines deal was found by Cheapflights users on 7/28. 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 8/263:35 pmMBJ - PDX
2 stops21h 09mAmerican Airlines
Wed 9/39:56 pmPDX - MBJ
1 stop12h 47mAmerican Airlines
Deal found 7/28$628
This Air Canada deal was found by Cheapflights users on 7/29. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/91:45 pmKIN - PDX
2 stops27h 01mAir Canada
Tue 9/163:25 pmPDX - KIN
2 stops19h 10mAir Canada
Deal found 7/29$640
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/129:00 amKIN - PDX
1 stop14h 47mDelta
Fri 9/1910:50 pmPDX - KIN
2 stops19h 10mDelta
Deal found 7/29$646

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 July 29, 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 10/28

7:00 am-10:27 pm

2 stops18h 27m

Portland

Tue 11/4

7:00 am-12:40 am

1 stop13h 40m

$399

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 10/16

7:10 am-9:02 pm

1 stop16h 52m

Portland

Tue 10/21

11:59 pm-2:25 pm

1 stop11h 26m

$408

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Mon 9/15

1:59 am-7:04 pm

3 stops20h 05m

Portland

Mon 9/22

8:04 pm-12:44 am

3 stops25h 40m

$411

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 9/11

11:59 am-11:12 am

3 stops26h 13m

Portland

Thu 9/18

8:04 pm-12:44 am

3 stops25h 40m

$434

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Thu 9/11

12:52 pm-10:42 pm

2 stops35h 50m

Portland

Thu 9/18

6:27 pm-1:30 pm

2 stops41h 03m

$467

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Fri 9/19

1:05 am-9:23 am

1 stop11h 18m

Portland

Fri 10/3

5:00 am-5:30 pm

1 stop9h 30m

$489

KingstonPortland

KIN - PDX

KINPDX

Kingston Norman Manley

Wed 9/10

12:08 pm-12:15 am

2 stops14h 07m

Portland

Wed 9/17

6:05 am-11:02 am

2 stops26h 57m

$504

KingstonPortland

KIN - PDX

KINPDX

Kingston Norman Manley

Wed 9/10

12:08 pm-7:04 pm

3 stops32h 56m

Portland

Wed 9/17

12:07 pm-11:02 am

3 stops20h 55m

$582

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Tue 8/26

12:19 pm-6:57 pm

3 stops32h 38m

Portland

Wed 9/3

7:52 pm-11:05 am

3 stops37h 13m

$582

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Tue 8/26

3:35 pm-10:44 am

2 stops21h 09m

Portland

Wed 9/3

9:56 pm-12:43 pm

1 stop12h 47m

$628

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 51 results
1
2
3
...
6

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 July 29, 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 July 29, 2025.
Read through reviews of airlines operating flights from Caribbean to Portland, such as Southwest, Delta, and LATAM Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,977 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
LATAM Airlines
7.5
Good
1,821 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,899 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • 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 $200 on Delta. Other airlines that offer cheap prices include Spirit Airlines from $212 and United Airlines from $245 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, Kingston Norman Manley - Portland or Santo Domingo Las Americas - 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
Lincoln City
McMinnville
Lake Oswego
Hillsboro
Astoria
Cannon Beach
Long Beach
Longview
Tigard
Depoe Bay
Woodburn
Stevenson
Wilsonville
Pacific City
Troutdale
Tillamook

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.
Dallas/Fort Worth to Portland flights
Los Angeles to Portland flights
O'Hare Intl to Portland flights
Ontario to Portland flights
Burbank to Portland flights
John F Kennedy Intl to Portland flights
San Francisco to Portland flights
Newark to Portland flights
Boston to Portland flights
Santa Ana to Portland flights
Dulles Intl to Portland flights
Reagan-National to Portland flights
Sky Harbor Intl to Portland flights
Minneapolis to Portland flights
San Diego to Portland flights
Hobby to Portland flights
San Jose to Portland flights
Love Field to Portland flights
Denver to Portland flights
LaGuardia to Portland flights
Austin to Portland flights
Detroit to Portland flights
Atlanta to Portland flights
Oakland to Portland flights
Baltimore to Portland flights
Orlando to Portland flights
Los Angeles to Boise flights
Salt Lake City to Portland flights
Sacramento to Portland flights
George Bush Intcntl to Portland flights
Denver to Boise flights
Philadelphia to Portland flights
Honolulu to Portland flights
Los Angeles to Redmond flights
San Francisco to Boise flights
Los Angeles to Eugene flights
Fresno to Portland flights
Palm Springs to Portland flights
Nashville to Portland flights
Burbank to Boise flights
Greensboro to Portland flights
Seattle to Boise flights
San Francisco to Redmond flights
O'Hare Intl to Boise flights
Manchester to Portland flights
Sacramento to Boise flights
Minneapolis to Boise flights
Las Vegas to Portland flights
Dallas/Fort Worth to Boise flights
Raleigh to Portland flights

Top 5 airlines flying from Caribbean to Portland

Discover the top 5 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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$232Average$394FlexibilityNo cancel feeOn-time62%
DeltaCheapest$290Average$516FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$348Average$586FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$406Average$632FlexibilityNo 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.