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$145+ 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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PWM
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap 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 December 12, 2025.

This Expedia deal was found by Cheapflights users on 12/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/156:05 amSJU - PWM
1 stop10h 08mJetBlue
Wed 12/174:35 pmPWM - SJU
1 stop7h 12mJetBlue
Deal found 12/11$355
This Delta deal was found by Cheapflights users on 12/11. 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.
Mon 12/151:55 pmSJU - PWM
1 stop9h 28mDelta
Wed 12/172:34 pmPWM - SJU
1 stop8h 25mDelta
Deal found 12/11$466
This Delta deal was found by Cheapflights users on 12/10. 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 12/126:35 pmSJU - PWM
1 stop6h 24mDelta
Mon 12/152:34 pmPWM - SJU
1 stop8h 25mDelta
Deal found 12/10$476
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/128:20 amSJU - PWM
1 stop14h 17mAmerican Airlines
Mon 12/155:34 amPWM - SJU
2 stops15h 35mAmerican Airlines
Deal found 12/11$481
This American Airlines deal was found by Cheapflights users on 12/11. 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.
Mon 12/158:20 amSJU - PWM
2 stops16h 17mAmerican Airlines
Wed 12/175:46 amPWM - SJU
2 stops15h 23mAmerican Airlines
Deal found 12/11$483
This Kiwi.com deal was found by Cheapflights users on 12/11. 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.
Sun 12/286:48 pmSJU - PWM
1 stop15h 18mMultiple Airlines
Sat 1/311:16 amPWM - SJU
2 stops25h 43mMultiple Airlines
Deal found 12/11$590
This American Airlines deal was found by Cheapflights users on 12/11. 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.
Sun 12/288:25 amSJU - PWM
1 stop15h 26mAmerican Airlines
Sat 1/35:45 amPWM - SJU
1 stop17h 14mAmerican Airlines
Deal found 12/11$623
This United Airlines deal was found by Cheapflights users on 12/11. 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.
Mon 12/158:10 amSJU - PWM
2 stops15h 59mUnited Airlines
Wed 12/176:00 amPWM - SJU
3 stops15h 22mUnited Airlines
Deal found 12/11$731

Find flight deals from Caribbean to Portland

Keep the following information in mind while searching for Caribbean to Portland flight deals. Data was last updated December 12, 2025.

Round-trip from

$356
(United Airlines)

One-way from

$242
(Kiwi.com)

Popular in

July

Cheapest in

February

Average price

$246
From Caribbean to Portland
Search Deals
One-way flight from Caribbean to Portland
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 12, 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

Fri 1/23

6:30 am-12:05 pm

1 stop6h 35m

Portland

Fri 1/30

12:40 pm-11:56 pm

1 stop10h 16m

$233

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Mon 3/2

2:05 am-3:14 pm

2 stops14h 09m

Portland

Wed 3/4

6:00 am-9:00 pm

2 stops14h 00m

$356

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sat 4/18

5:40 am-1:23 pm

1 stop7h 43m

$145

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sun 2/22

6:00 am-10:49 am

1 stop29h 49m

$247

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sat 4/25

5:40 am-1:23 pm

1 stop7h 43m

$250

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sat 4/18

6:25 am-4:00 pm

2 stops9h 35m

$278

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sat 4/25

5:40 am-4:36 pm

2 stops10h 56m

$581

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sat 4/18

9:49 pm-4:26 pm

3 stops42h 37m

$652

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

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 $53). Flying from Caribbean to Portland, Maine in November is currently the most expensive (average of $141). 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 December 12, 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 50% 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 December 12, 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
8,008 reviews

Overall

7.9

Boarding

8.1

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,008 reviews
Delta
7.9
Good
8,008 reviews

Overall

7.9

Boarding

8.1

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,095 reviews
Delta
7.9
Good
8,008 reviews

Overall

7.9

Boarding

8.1

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,050 reviews
Delta
7.9
Good
8,008 reviews

Overall

7.9

Boarding

8.1

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 14h 09m. Airlines will cover a distance of 1758 mi.

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

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $120. Users have also found prices from $124 and $218 on JetBlue and American Airlines, respectively.

  • 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 $53). Flying from Caribbean to Portland, Maine in November is currently the most expensive (average of $141). 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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$370Average$538FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$383Average$530FlexibilityNo cancel feeOn-time69%

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