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$279+ Cheap flights from Caribbean to Portland, ME (PWM)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PWM
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 March 28, 2025.

Round-trip from

$279
(JetBlue)

Popular in

April

Cheapest in

February

Average price

$348
From Caribbean to Portland
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($65 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($27 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2025
Search Deals

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 March 28, 2025.

This JetBlue deal was found by Cheapflights users on 3/26. 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.
Wed 5/287:01 amSJU - PWM
1 stop7h 39mJetBlue
Sat 5/312:15 pmPWM - SJU
1 stop7h 15mJetBlue
Deal found 3/26$279
This Booking.com deal was found by Cheapflights users on 3/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/215:45 amSJU - PWM
1 stop8h 25mFrontier
Thu 4/248:01 pmPWM - SJU
1 stop26h 01mFrontier
Deal found 3/27$326
This American Airlines deal was found by Cheapflights users on 3/26. 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.
Fri 8/155:30 amSJU - PWM
1 stop12h 10mAmerican Airlines
Sat 8/2310:58 amPWM - SJU
2 stops10h 47mAmerican Airlines
Deal found 3/26$396
This Delta deal was found by Cheapflights users on 3/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/17:00 amSJU - PWM
1 stop6h 59mDelta
Sun 10/55:30 amPWM - SJU
1 stop6h 33mDelta
Deal found 3/26$460
This United Airlines deal was found by Cheapflights users on 3/26. 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.
Tue 9/301:05 amSJU - PWM
2 stops9h 39mUnited Airlines
Sun 10/56:00 amPWM - SJU
1 stop7h 45mUnited Airlines
Deal found 3/26$551

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 March 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

Wed 5/28

7:01 am-2:40 pm

1 stop7h 39m

Portland

Sat 5/31

2:15 pm-9:30 pm

1 stop7h 15m

$279

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Mon 4/21

5:45 am-2:10 pm

1 stop8h 25m

Portland

Thu 4/24

8:01 pm-10:02 pm

1 stop26h 01m

$326

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 8/15

5:30 am-5:40 pm

1 stop12h 10m

Portland

Sat 8/23

10:58 am-9:45 pm

2 stops10h 47m

$396

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Tue 5/27

2:05 am-5:43 pm

2 stops15h 38m

Portland

Sat 5/31

6:10 am-1:45 pm

1 stop7h 35m

$653

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

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, January is the cheapest month in which you can book a flight from Caribbean to Portland, Maine (average of $296). Flying from Caribbean to Portland, Maine in April is currently the most expensive (average of $423). 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 March 28, 2025.

When flying from Caribbean to Portland, Maine, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Portland by month

Plan your trip to Portland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Portland, Maine ranges from 2.9 - 4.5 inches per month. November is typically the wettest month, when rainfall can reach 4.5 in. August is typically the driest time to visit Portland, Maine when rainfall is around 2.9 in.

Temperature in Portland by month

Plan your trip to Portland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Portland, Maine, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 March 28, 2025.
United Airlines
7.4
Good
8,603 reviews

Entertainment

7.0

Overall

7.4

Comfort

7.3

Food

6.6

Boarding

7.7

Crew

8.1

Reviews

1 / 20
4.0
Okay

Patti,Feb 2025

FCO - EWR

The food was inedible! We are in the food business and aren’t sure who got this contract. But prisoners eat better. The food was so bad. I ate just a small amount and it made me nauseous. Everything is over microwaved too. And what is with the options? Vegan and vegetarian, but no keto or carnivore? I get that may be more expensive. But I’d gladly pay if it even was an option. But it’s not. There are many fresh options that could have been offered that don’t have to be heated too!
United Airlines
7.4
Good
8,603 reviews
United Airlines
7.4
Good
8,603 reviews

Entertainment

7.0

Overall

7.4

Comfort

7.3

Food

6.6

Boarding

7.7

Crew

8.1

Reviews

1 / 20
4.0
Okay

Patti,Feb 2025

FCO - EWR

The food was inedible! We are in the food business and aren’t sure who got this contract. But prisoners eat better. The food was so bad. I ate just a small amount and it made me nauseous. Everything is over microwaved too. And what is with the options? Vegan and vegetarian, but no keto or carnivore? I get that may be more expensive. But I’d gladly pay if it even was an option. But it’s not. There are many fresh options that could have been offered that don’t have to be heated too!
JetBlue
7.3
Good
2,923 reviews
United Airlines
7.4
Good
8,603 reviews

Entertainment

7.0

Overall

7.4

Comfort

7.3

Food

6.6

Boarding

7.7

Crew

8.1

Reviews

1 / 20
4.0
Okay

Patti,Feb 2025

FCO - EWR

The food was inedible! We are in the food business and aren’t sure who got this contract. But prisoners eat better. The food was so bad. I ate just a small amount and it made me nauseous. Everything is over microwaved too. And what is with the options? Vegan and vegetarian, but no keto or carnivore? I get that may be more expensive. But I’d gladly pay if it even was an option. But it’s not. There are many fresh options that could have been offered that don’t have to be heated too!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,603 reviews

Entertainment

7.0

Overall

7.4

Comfort

7.3

Food

6.6

Boarding

7.7

Crew

8.1

Reviews

1 / 20
4.0
Okay

Patti,Feb 2025

FCO - EWR

The food was inedible! We are in the food business and aren’t sure who got this contract. But prisoners eat better. The food was so bad. I ate just a small amount and it made me nauseous. Everything is over microwaved too. And what is with the options? Vegan and vegetarian, but no keto or carnivore? I get that may be more expensive. But I’d gladly pay if it even was an option. But it’s not. There are many fresh options that could have been offered that don’t have to be heated too!
Frontier
6.0
Okay
3,271 reviews
United Airlines
7.4
Good
8,603 reviews

Entertainment

7.0

Overall

7.4

Comfort

7.3

Food

6.6

Boarding

7.7

Crew

8.1

Reviews

1 / 20
4.0
Okay

Patti,Feb 2025

FCO - EWR

The food was inedible! We are in the food business and aren’t sure who got this contract. But prisoners eat better. The food was so bad. I ate just a small amount and it made me nauseous. Everything is over microwaved too. And what is with the options? Vegan and vegetarian, but no keto or carnivore? I get that may be more expensive. But I’d gladly pay if it even was an option. But it’s not. There are many fresh options that could have been offered that don’t have to be heated too!

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.

  • 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, January is the cheapest month in which you can book a flight from Caribbean to Portland, Maine (average of $296). Flying from Caribbean to Portland, Maine in April is currently the most expensive (average of $423). 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 Caribbean?

Book flights to Caribbean if you plan to visit one of these locations
North Conway
Bath
Brunswick
Auburn
Conway
Lewiston

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Top 4 airlines flying from Caribbean to Portland

Discover the top 4 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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$389Average$406FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$413Average$575FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$420Average$680FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$428Average$515FlexibilityNo cancel feeOn-time62%
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