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$118+ Cheap flights from Caribbean Islands 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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PWM
Nov 7 — Nov 141
Fri 11/7
Fri 11/14
1 adult, Economy
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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 8, 2025.

This American Airlines deal was found by Cheapflights users on 10/8. 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
2 stops16h 17mAmerican Airlines
Mon 12/157:02 amPWM - SJU
1 stop14h 07mAmerican Airlines
Deal found 10/8$380
This Southwest deal was found by Cheapflights users on 10/8. 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.
Fri 12/126:10 amSJU - PWM
1 stop9h 15mSouthwest
Mon 12/1512:45 pmPWM - SJU
1 stop9h 35mSouthwest
Deal found 10/8$422
This JetBlue deal was found by Cheapflights users on 10/6. 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.
Mon 10/136:00 amSJU - PWM
1 stop7h 22mJetBlue
Wed 10/152:17 pmPWM - SJU
1 stop6h 37mJetBlue
Deal found 10/6$558
This United Airlines deal was found by Cheapflights users on 10/6. 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.
Sun 10/121:05 amSJU - PWM
1 stop8h 06mUnited Airlines
Wed 10/153:45 pmPWM - SJU
1 stop8h 12mUnited Airlines
Deal found 10/6$561
This United Airlines deal was found by Cheapflights users on 10/8. 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 12/112:05 amSJU - PWM
1 stop8h 05mUnited Airlines
Mon 12/156:00 amPWM - SJU
1 stop7h 40mUnited Airlines
Deal found 10/8$608
This Southwest deal was found by Cheapflights users on 10/6. 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.
Mon 12/226:05 amSJU - PWM
2 stops11h 50mSouthwest
Sat 12/273:05 pmPWM - SJU
1 stop8h 25mSouthwest
Deal found 10/6$770

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 8, 2025.

Round-trip from

$295
(American Airlines)

One-way from

$118
(United Airlines)
From Caribbean Islands to Portland
Search Deals
One-way flight from Caribbean Islands to Portland
Search Deals

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 8, 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 - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Wed 2/18

4:45 pm-12:09 pm

2 stops20h 24m

Portland

Sat 2/21

1:16 pm-11:30 pm

1 stop9h 14m

$295

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 12/12

11:00 am-11:37 pm

2 stops13h 37m

Portland

Mon 12/15

5:34 am-10:09 pm

2 stops15h 35m

$380

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Wed 2/18

6:00 am-2:26 pm

1 stop9h 26m

Portland

Sat 2/21

3:25 pm-12:50 am

1 stop8h 25m

$414

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 12/12

6:10 am-2:25 pm

1 stop9h 15m

Portland

Mon 12/15

12:45 pm-11:20 pm

1 stop9h 35m

$422

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Thu 12/11

2:05 am-2:22 pm

2 stops13h 17m

Portland

Mon 12/15

6:00 am-2:40 pm

1 stop7h 40m

$608

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 10/31

1:20 pm-11:59 pm

2 stops10h 39m

$118

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 10/31

5:30 am-3:11 pm

1 stop9h 41m

$118

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Tue 2/17

5:56 pm-11:49 pm

1 stop6h 53m

$182

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sun 10/26

5:30 am-8:47 pm

1 stop15h 17m

$218

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sun 1/11

5:20 pm-4:26 pm

2 stops24h 06m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

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, Maine?

Currently, February is the cheapest month in which you can book a flight from Caribbean Islands to Portland, Maine (average of $55). Flying from Caribbean Islands 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 EPX to PWM?

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 8, 2025.

One of the essential ways to save on airfare from Caribbean Islands 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 October 8, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American Airlines from Caribbean Islands to Portland by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,969 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Delta
8.0
Very good
7,969 reviews
Delta
8.0
Very good
7,969 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
United Airlines
7.4
Good
8,964 reviews
Delta
8.0
Very good
7,969 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
American Airlines
7.2
Good
11,042 reviews
Delta
8.0
Very good
7,969 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

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?

    Located just 2.9 mi from the city center, Portland (PWM) is the airport most travelers will use when flying to Portland from Caribbean Islands.

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

    For as low as $295, American Airlines can have you in Portland, Maine from Caribbean Islands in 20h 24m. The distance from Caribbean Islands to Portland, Maine is about 1758 mi.

  • 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, Maine?

    Currently, February is the cheapest month in which you can book a flight from Caribbean Islands to Portland, Maine (average of $55). Flying from Caribbean Islands 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 Islands to Portland

Discover the top 2 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 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$370Average$538FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$383Average$530FlexibilityNo cancel feeOn-time69%

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