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$118+ Cheap flights from Caribbean to Portland, ME (PWM)

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 2/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PWM
nov. 27 — dic. 41
jue. 11/27
jue. 12/4
1 adult, Economy
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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 octubre 28, 2025.

Round-trip from

$295
(American Airlines)

One-way from

$118
(American Airlines)

Popular in

April

Cheapest in

February

Average price

$442
From Caribbean to Portland
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One-way flight from Caribbean to Portland
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Highest demand for flights based on searches. 15% potential increase in price ($76 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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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 octubre 28, 2025.

This Southwest deal was found by Cheapflights users on 10/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/65:55 pmSJU - PWM
1 stop7h 25mSouthwest
mié. 11/1212:45 pmPWM - SJU
2 stops10h 50mSouthwest
Deal found 10/27$355
This United Airlines deal was found by Cheapflights users on 10/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/52:05 amSJU - PWM
2 stops13h 14mUnited Airlines
mié. 11/123:20 pmPWM - SJU
1 stop8h 16mUnited Airlines
Deal found 10/27$370
This American Airlines deal was found by Cheapflights users on 10/26. 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.
vie. 12/1211:00 amSJU - PWM
2 stops13h 37mAmerican Airlines
lun. 12/155:34 amPWM - SJU
2 stops15h 35mAmerican Airlines
Deal found 10/26$378
This Delta deal was found by Cheapflights users on 10/28. 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.
vie. 12/126:35 pmSJU - PWM
1 stop6h 24mDelta
lun. 12/152:34 pmPWM - SJU
1 stop8h 25mDelta
Deal found 10/28$490
This United Airlines deal was found by Cheapflights users on 10/28. 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.
jue. 12/112:05 amSJU - PWM
1 stop8h 05mUnited Airlines
lun. 12/156:00 amPWM - SJU
1 stop7h 40mUnited Airlines
Deal found 10/28$650
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/124:24 pmSJU - PWM
1 stop26h 14mMultiple Airlines
vie. 12/196:05 pmPWM - SJU
2 stops29h 49mMultiple Airlines
Deal found 10/27$654

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 octubre 28, 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 - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

mié. 2/18

5:41 am-10:32 pm

2 stops17h 51m

Portland

sáb. 2/21

5:40 am-10:35 pm

2 stops15h 55m

$295

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

vie. 12/12

11:00 am-11:37 pm

2 stops13h 37m

Portland

lun. 12/15

5:34 am-10:09 pm

2 stops15h 35m

$378

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

vie. 12/12

2:10 pm-11:59 pm

1 stop10h 49m

Portland

lun. 12/15

2:34 pm-11:59 pm

1 stop8h 25m

$490

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

mié. 2/18

8:10 am-2:23 pm

1 stop7h 13m

Portland

sáb. 2/21

3:05 pm-12:36 am

1 stop8h 31m

$502

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

dom. 2/15

5:09 pm-10:59 pm

1 stop6h 50m

$118

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

dom. 12/7

6:25 am-11:00 pm

1 stop17h 35m

$181

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

dom. 12/7

12:00 pm-9:06 am

2 stops22h 06m

$217

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

dom. 2/15

8:10 am-9:14 pm

2 stops14h 04m

$258

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

mar. 2/17

9:25 am-10:59 pm

1 stop14h 34m

$261

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

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, Maine?

Currently, February is the cheapest month in which you can book a flight from Caribbean to Portland, Maine (average of $56). Flying from Caribbean to Portland, Maine in July is currently the most expensive (average of $137). 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 PWM?

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 octubre 28, 2025.

One of the essential ways to save on airfare from Caribbean to Portland, Maine is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 47% on airfare.

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 octubre 28, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American Airlines from Caribbean to Portland by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,994 reviews

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
Delta
7.9
Good
7,994 reviews
Delta
7.9
Good
7,994 reviews

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
United Airlines
7.4
Good
9,001 reviews
Delta
7.9
Good
7,994 reviews

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
American Airlines
7.2
Good
11,032 reviews
Delta
7.9
Good
7,994 reviews

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!

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?

    Most people fly into Portland (PWM) if they book a flight to Portland from Caribbean. Portland is conveniently located just 2.9 mi from Portland’s city center.

  • How long is the flight from Caribbean to Portland, Maine?

    Departing from Caribbean to Portland, Maine will take you 17h 51m. Airlines will cover a distance of 1758 mi.

  • 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, Maine?

    Currently, February is the cheapest month in which you can book a flight from Caribbean to Portland, Maine (average of $56). Flying from Caribbean to Portland, Maine in July is currently the most expensive (average of $137). 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
North Conway
Brunswick
Auburn
Conway

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Top 2 airlines flying from Caribbean to Portland

Discover the top 2 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 octubre 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$370Average$538FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$383Average$530FlexibilityNo cancel feeOn-time69%

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