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$106+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PWM
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
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 January 27, 2026.

This JetBlue deal was found by Cheapflights users on 1/26. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:25 am
SJU
-
PWM
1 stop6h 58m
JetBlue
Fri 5/82:18 pm
PWM
-
SJU
1 stop9h 49m
JetBlue
Deal found 1/26$225
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Wed 4/291:00 am
SJU
-
PWM
1 stop7h 49m
United Airlines
Sat 5/95:30 am
PWM
-
SJU
2 stops15h 04m
United Airlines
Deal found 1/27$300
This United Airlines deal was found by Cheapflights users on 1/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/291:00 am
SJU
-
PWM
1 stop7h 49m
United Airlines
Fri 5/89:39 am
PWM
-
SJU
1 stop10h 55m
United Airlines
Deal found 1/26$333
This Southwest deal was found by Cheapflights users on 1/27. 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.
Thu 4/302:00 pm
SJU
-
PWM
2 stops9h 25m
Southwest
Sat 5/95:40 am
PWM
-
SJU
2 stops9h 10m
Southwest
Deal found 1/27$365
This Southwest deal was found by Cheapflights users on 1/27. 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.
Thu 4/302:00 pm
SJU
-
PWM
2 stops9h 25m
Southwest
Fri 5/82:50 pm
PWM
-
SJU
2 stops9h 05m
Southwest
Deal found 1/27$378
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Wed 4/19:20 am
SJU
-
PWM
1 stop8h 44m
American Airlines
Sun 4/57:00 am
PWM
-
SJU
1 stop16h 52m
American Airlines
Deal found 1/27$447
This United Airlines deal was found by Cheapflights users on 1/25. 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 2/45:50 pm
SJU
-
PWM
1 stop21h 41m
United Airlines
Sun 2/86:00 am
PWM
-
SJU
2 stops14h 00m
United Airlines
Deal found 1/25$510
This Southwest deal was found by Cheapflights users on 1/27. 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.
Wed 4/15:55 am
SJU
-
PWM
2 stops10h 00m
Southwest
Sun 4/512:35 pm
PWM
-
SJU
2 stops13h 05m
Southwest
Deal found 1/27$567

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 January 27, 2026.

Round-trip from

$225
(JetBlue)

One-way from

$106
(United Airlines)
From Caribbean to Portland
Search Deals
One-way flight from Caribbean to Portland
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 January 27, 2026.
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

Thu 4/30

6:25 am-1:23 pm

1 stop6h 58m

Portland

Fri 5/8

2:18 pm-12:07 am

1 stop9h 49m

$225

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Thu 4/30

6:25 am-1:23 pm

1 stop6h 58m

Portland

Sat 5/9

2:18 pm-12:07 am

1 stop9h 49m

$225

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Wed 4/29

1:00 am-8:49 am

1 stop7h 49m

Portland

Sat 5/9

5:30 am-8:34 pm

2 stops15h 04m

$300

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Wed 4/29

1:00 am-8:49 am

1 stop7h 49m

Portland

Fri 5/8

9:39 am-8:34 pm

1 stop10h 55m

$333

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Thu 4/30

2:00 pm-11:25 pm

2 stops9h 25m

Portland

Sat 5/9

5:40 am-2:50 pm

2 stops9h 10m

$365

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Thu 4/30

4:25 pm-11:25 pm

1 stop7h 00m

Portland

Fri 5/8

2:50 pm-11:55 pm

2 stops9h 05m

$365

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Wed 4/1

9:20 am-6:04 pm

1 stop8h 44m

Portland

Sun 4/5

7:00 am-11:52 pm

1 stop16h 52m

$447

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 5/1

1:00 am-2:14 pm

2 stops13h 14m

$106

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sat 6/6

3:30 am-1:23 pm

1 stop9h 53m

$145

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sat 5/2

7:15 am-2:11 pm

1 stop6h 56m

$164

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 16 results
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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 $65). 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.

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 January 27, 2026.
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
8,119 reviews

Crew

8.5

Food

7.2

Entertainment

7.8

Overall

7.9

Boarding

8.1

Comfort

7.9

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
8,119 reviews
Delta
7.9
Good
8,119 reviews

Crew

8.5

Food

7.2

Entertainment

7.8

Overall

7.9

Boarding

8.1

Comfort

7.9

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
9,205 reviews
Delta
7.9
Good
8,119 reviews

Crew

8.5

Food

7.2

Entertainment

7.8

Overall

7.9

Boarding

8.1

Comfort

7.9

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
11,197 reviews
Delta
7.9
Good
8,119 reviews

Crew

8.5

Food

7.2

Entertainment

7.8

Overall

7.9

Boarding

8.1

Comfort

7.9

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 6h 58m. Airlines will cover a distance of 1758 mi. This flight may include one or multiple stops.

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

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $118. Users have also found prices from $124 and $138 on JetBlue and Delta, 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 $65). 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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$370Average$538FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$383Average$530FlexibilityNo cancel feeOn-time69%

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