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$200+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
Aug 9 — Aug 161
Sat 8/9
Sat 8/16
1 adult, Economy
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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 August 4, 2025.

Round-trip from

$399
(Delta)

One-way from

$200
(Delta)
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 August 4, 2025.

This Delta deal was found by Cheapflights users on 8/4. 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 10/287:00 amSJU - PDX
2 stops18h 27mDelta
Mon 11/312:50 amPDX - SJU
2 stops12h 43mDelta
Deal found 8/4$399
This American Airlines deal was found by Cheapflights users on 8/4. 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 55mAmerican Airlines
Tue 10/2111:59 pmPDX - SJU
1 stop11h 26mAmerican Airlines
Deal found 8/4$408
This Mytrip deal was found by Cheapflights users on 8/4. 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 8/214:12 pmSJU - PDX
2 stops29h 45mSpirit Airlines
Tue 8/267:52 pmPDX - SJU
3 stops25h 05mSpirit Airlines
Deal found 8/4$474
This United Airlines deal was found by Cheapflights users on 8/4. 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 10/21:05 amSJU - PDX
1 stop10h 48mUnited Airlines
Sun 10/1211:59 pmPDX - SJU
1 stop11h 45mUnited Airlines
Deal found 8/4$484
This Mytrip deal was found by Cheapflights users on 8/4. 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 8/182:11 amSJU - PDX
3 stops18h 35mMultiple Airlines
Fri 8/228:46 amPDX - SJU
3 stops27h 24mMultiple Airlines
Deal found 8/4$504
This American Airlines deal was found by Cheapflights users on 8/3. 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.
Fri 8/223:30 pmPUJ - PDX
1 stop20h 54mAmerican Airlines
Sun 8/319:52 pmPDX - PUJ
1 stop10h 13mAmerican Airlines
Deal found 8/3$551
This Southwest deal was found by Cheapflights users on 8/3. 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 8/278:00 amSJU - PDX
2 stops13h 25mSouthwest
Wed 9/36:10 amPDX - SJU
2 stops10h 35mSouthwest
Deal found 8/3$565
This Delta deal was found by Cheapflights users on 8/4. 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 9/59:25 amKIN - PDX
1 stop14h 47mDelta
Thu 9/1810:50 pmPDX - KIN
2 stops19h 10mDelta
Deal found 8/4$646
This Mytrip deal was found by Cheapflights users on 8/3. 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.
Sat 9/278:50 amGCM - PDX
3 stops28h 21mMultiple Airlines
Thu 10/28:18 pmPDX - GCM
3 stops23h 02mMultiple Airlines
Deal found 8/3$664
This United Airlines deal was found by Cheapflights users on 8/3. 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 9/271:35 pmGCM - PDX
1 stop10h 52mUnited Airlines
Thu 10/210:46 amPDX - GCM
2 stops47h 44mUnited Airlines
Deal found 8/3$674
This Delta deal was found by Cheapflights users on 8/3. 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 9/2712:52 pmGCM - PDX
1 stop10h 55mDelta
Thu 10/210:05 pmPDX - GCM
1 stop11h 31mDelta
Deal found 8/3$699
This Delta deal was found by Cheapflights users on 8/3. 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 8/221:05 pmPUJ - PDX
1 stop12h 07mDelta
Sat 8/3012:46 amPDX - PUJ
2 stops10h 48mDelta
Deal found 8/3$1,005

Cheapflights Fare Finder

 
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 August 4, 2025.
Use the filters below to find and compare flights from Caribbean Islands to Portland that are best for you.

Fly from

Caribbean Islands

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

Mon 11/3

12:50 am-5:33 pm

2 stops12h 43m

$399

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 1/29

2:45 pm-11:29 pm

1 stop12h 44m

Portland

Tue 2/10

5:53 am-12:05 am

2 stops14h 12m

$408

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 8/21

4:12 pm-6:57 pm

2 stops29h 45m

Portland

Tue 8/26

7:52 pm-11:57 pm

3 stops25h 05m

$474

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 10/2

1:05 am-8:53 am

1 stop10h 48m

Portland

Sun 10/12

11:59 pm-2:44 pm

1 stop11h 45m

$484

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Mon 8/18

2:11 am-5:46 pm

3 stops18h 35m

Portland

Fri 8/22

8:46 am-3:10 pm

3 stops27h 24m

$504

Punta CanaPortland

PUJ - PDX

PUJPDX

Punta Cana

Fri 8/22

3:30 pm-9:24 am

1 stop20h 54m

Portland

Sun 8/31

9:52 pm-11:05 am

1 stop10h 13m

$551

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Wed 8/27

8:00 am-6:25 pm

2 stops13h 25m

Portland

Wed 9/3

6:10 am-7:45 pm

2 stops10h 35m

$565

Santo DomingoPortland

SDQ - PDX

SDQPDX

Santo Domingo Las Americas

Thu 1/29

2:55 pm-11:33 pm

1 stop12h 38m

Portland

Fri 2/6

7:00 am-11:59 pm

1 stop12h 59m

$575

KingstonPortland

KIN - PDX

KINPDX

Kingston Norman Manley

Fri 9/5

9:25 am-10:12 pm

1 stop14h 47m

Portland

Thu 9/18

10:50 pm-8:00 pm

2 stops19h 10m

$646

George TownPortland

GCM - PDX

GCMPDX

George Town Owen Roberts Intl

Sat 9/27

8:50 am-11:11 am

3 stops28h 21m

Portland

Thu 10/2

8:18 pm-9:20 pm

3 stops23h 02m

$664

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/4

Showing 1-10 of 41 results
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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.

Cheapflights Insights

Everything you need to know about your flight from Caribbean Islands to Portland

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 $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 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 August 4, 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.

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 August 4, 2025.
Read through reviews of airlines operating flights from Caribbean Islands to Portland, such as Alaska Airlines, Southwest, and Delta. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Delta
8.0
Very good
7,987 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
LATAM Airlines
7.5
Good
1,830 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
United Airlines
7.4
Good
8,912 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Food

7.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)

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 most popular routes from Caribbean Islands to Portland?

    Most travelers choose San Juan Luis Munoz Marin Intl - Portland, Kingston Norman Manley - Portland or Montego Bay Sangster 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 $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
Lincoln City
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

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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 August 4, 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%

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