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$195+ 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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
Oct 31 — Nov 71
Fri 10/31
Fri 11/7
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 October 1, 2025.

Round-trip from

$419
(Delta)

One-way from

$195
(Kiwi.com)
From Caribbean Islands to Portland
Search Deals
One-way flight from Caribbean Islands to Portland
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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 October 1, 2025.

This Delta deal was found by Cheapflights users on 10/1. 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
Tue 11/1111:15 pmPDX - SJU
1 stop10h 55mDelta
Deal found 10/1$419
This American Airlines deal was found by Cheapflights users on 9/30. 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 11/1111:13 amSJU - PDX
1 stop16h 18mAmerican Airlines
Mon 11/177:40 amPDX - SJU
2 stops12h 18mAmerican Airlines
Deal found 9/30$426
This American Airlines deal was found by Cheapflights users on 9/30. 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
Sun 11/910:15 pmPDX - SJU
1 stop18h 33mAmerican Airlines
Deal found 9/30$427
This United Airlines deal was found by Cheapflights users on 9/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/221:05 amSJU - PDX
2 stops13h 53mUnited Airlines
Sun 10/265:00 amPDX - SJU
2 stops12h 00mUnited Airlines
Deal found 9/29$443
This eDestinos deal was found by Cheapflights users on 9/30. 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 11/103:59 amSJU - PDX
3 stops59h 57mMultiple Airlines
Sun 11/167:30 amPDX - SJU
2 stops30h 24mMultiple Airlines
Deal found 9/30$459
This American Airlines deal was found by Cheapflights users on 9/30. 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 12/1712:49 pmSJU - PDX
1 stop15h 03mAmerican Airlines
Tue 1/610:59 pmPDX - SJU
1 stop14h 02mAmerican Airlines
Deal found 9/30$466
This American Airlines deal was found by Cheapflights users on 9/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/257:10 amSJU - PDX
2 stops15h 17mAmerican Airlines
Tue 10/2811:59 pmPDX - SJU
2 stops12h 55mAmerican Airlines
Deal found 9/29$473
This Delta deal was found by Cheapflights users on 9/29. 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.
Thu 10/2312:46 pmSJU - PDX
1 stop12h 22mDelta
Sat 10/2512:40 amPDX - SJU
2 stops12h 45mDelta
Deal found 9/29$482
This eDestinos deal was found by Cheapflights users on 9/30. 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 11/103:59 amSJU - PDX
2 stops44h 34mMultiple Airlines
Mon 11/175:30 pmPDX - SJU
2 stops20h 24mMultiple Airlines
Deal found 9/30$485
This Sun Country Air deal was found by Cheapflights users on 9/28. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:02 pmSJU - PDX
1 stop28h 12mSun Country Air
Mon 12/296:49 pmPDX - SJU
1 stop17h 24mSun Country Air
Deal found 9/28$494
This American Airlines deal was found by Cheapflights users on 9/30. 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 12/2310:26 amSJU - PDX
1 stop18h 33mAmerican Airlines
Sat 1/310:49 pmPDX - SJU
1 stop12h 59mAmerican Airlines
Deal found 9/30$495
This American Airlines deal was found by Cheapflights users on 10/1. 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 11/17:00 amKIN - PDX
2 stops14h 26mAmerican Airlines
Fri 2/1311:11 pmPDX - KIN
1 stop9h 34mAmerican Airlines
Deal found 10/1$710

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 October 1, 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

Fri 10/24

1:05 am-1:03 pm

2 stops14h 58m

Portland

Tue 10/28

5:00 am-5:25 pm

1 stop9h 25m

$419

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 11/11

7:59 pm-2:10 pm

2 stops14h 11m

$419

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Tue 10/28

7:00 am-10:27 pm

2 stops18h 27m

Portland

Sun 11/9

11:15 pm-2:10 pm

1 stop10h 55m

$419

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Tue 10/28

7:00 am-10:27 pm

2 stops18h 27m

Portland

Sat 11/8

5:00 pm-12:56 pm

2 stops15h 56m

$419

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Tue 10/28

3:00 pm-11:06 pm

1 stop11h 06m

Portland

Sun 11/9

10:15 pm-8:48 pm

1 stop18h 33m

$427

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Mon 11/10

3:59 am-11:56 am

3 stops59h 57m

Portland

Mon 11/17

5:30 pm-5:54 pm

2 stops20h 24m

$466

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Mon 12/22

5:02 pm-5:14 pm

1 stop28h 12m

Portland

Mon 12/29

6:49 pm-4:13 pm

1 stop17h 24m

$494

Punta CanaPortland

PUJ - PDX

PUJPDX

Punta Cana

Fri 2/27

2:05 pm-9:18 pm

1 stop11h 13m

Portland

Tue 3/3

5:05 am-6:18 pm

1 stop9h 13m

$542

Punta CanaPortland

PUJ - PDX

PUJPDX

Punta Cana

Fri 2/27

6:05 pm-11:05 am

1 stop21h 00m

Portland

Mon 3/2

12:55 am-3:56 pm

1 stop11h 01m

$542

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

Sat 2/28

8:00 am-7:18 pm

1 stop14h 18m

Portland

Tue 3/3

9:45 pm-3:15 pm

1 stop14h 30m

$543

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/1

Showing 1-10 of 49 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 October 1, 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 October 1, 2025.
Read through reviews of airlines operating flights from Caribbean Islands to Portland, such as United Airlines and American Airlines. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,929 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Overall

7.4

Food

6.6

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
United Airlines
7.4
Good
8,929 reviews
United Airlines
7.4
Good
8,929 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Overall

7.4

Food

6.6

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
American Airlines
7.2
Good
11,030 reviews
United Airlines
7.4
Good
8,929 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Overall

7.4

Food

6.6

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.

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.

  • How long is the flight from Caribbean Islands to Portland?

    For as low as $797, United Airlines can have you in Portland from Caribbean Islands in 13h 54m. The distance from Caribbean Islands to Portland is about 2961 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    The cheapest airline one-way is Sun Country Air, with whom users have recently found tickets for as low as $198. However, be on the lookout for offers from Delta and American Airlines, 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, Kingston Norman Manley - Portland or Puerto Plata La Union - 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
Lincoln City
Lake Oswego
Hillsboro
McMinnville
Cannon Beach
Long Beach
Longview
Tigard
The Dalles
Depoe Bay
Stevenson
Wilsonville
Pacific City
Tillamook
Troutdale
Gresham

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Top 4 airlines flying from Caribbean Islands to Portland

Discover the top 4 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 October 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$242Average$512FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$353Average$588FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$406Average$601FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$466Average$565FlexibilityNo cancel feeOn-time63%

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