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$159+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PWM
May 4 — May 111
Sun 5/4
Sun 5/11
1 adult, Economy
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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 April 29, 2025.

Round-trip from

$363
(United Airlines)

One-way from

$159
(Frontier)
From Caribbean Islands to Portland
Search Deals
One-way flight from Caribbean Islands to Portland
Search Deals

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 April 29, 2025.

This United Airlines deal was found by Cheapflights users on 4/28. 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.
Wed 6/111:25 pmSJU - PWM
2 stops10h 32mUnited Airlines
Sun 6/156:20 amPWM - SJU
1 stop7h 25mUnited Airlines
Deal found 4/28$363
This Delta deal was found by Cheapflights users on 4/28. 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.
Wed 6/117:00 amSJU - PWM
1 stop6h 54mDelta
Sun 6/156:30 amPWM - SJU
1 stop9h 58mDelta
Deal found 4/28$375
This American Airlines deal was found by Cheapflights users on 4/27. 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 5/215:25 amSJU - PWM
1 stop7h 09mAmerican Airlines
Wed 5/214:01 pmPWM - SJU
1 stop6h 29mAmerican Airlines
Deal found 4/27$526
This JetBlue deal was found by Cheapflights users on 4/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/143:25 amSJU - PWM
1 stop9h 58mJetBlue
Sat 8/232:20 pmPWM - SJU
1 stop10h 34mJetBlue
Deal found 4/28$536

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 April 29, 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 6/11

1:25 pm-11:57 pm

2 stops10h 32m

Portland

Sun 6/15

6:20 am-1:45 pm

1 stop7h 25m

$363

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Wed 6/11

7:00 am-1:54 pm

1 stop6h 54m

Portland

Sun 6/15

6:30 am-4:28 pm

1 stop9h 58m

$375

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Wed 5/21

5:25 am-12:34 pm

1 stop7h 09m

Portland

Wed 5/21

4:01 pm-10:30 pm

1 stop6h 29m

$526

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Mon 5/5

6:00 am-8:40 pm

1 stop14h 40m

$159

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Tue 5/13

7:01 am-2:40 pm

1 stop7h 39m

$187

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Tue 5/13

6:10 am-4:51 pm

2 stops10h 41m

$211

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Mon 5/5

1:25 pm-11:59 pm

2 stops10h 34m

$218

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Mon 5/12

1:59 am-7:40 pm

3 stops41h 41m

$333

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

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, January is the cheapest month in which you can book a flight from Caribbean Islands to Portland, Maine (average of $296). Flying from Caribbean Islands to Portland, Maine in May is currently the most expensive (average of $416). 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 April 29, 2025.

When flying from Caribbean Islands 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 April 29, 2025.
Delta
8.0
Very good
7,929 reviews

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,929 reviews
Delta
8.0
Very good
7,929 reviews

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,929 reviews

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
JetBlue
7.3
Good
2,922 reviews
Delta
8.0
Very good
7,929 reviews

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,929 reviews

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Frontier
6.0
Okay
3,285 reviews
Delta
8.0
Very good
7,929 reviews

Comfort

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $159. JetBlue flights start at $187 while deals on American Airlines start at $211 one-way.

  • 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, January is the cheapest month in which you can book a flight from Caribbean Islands to Portland, Maine (average of $296). Flying from Caribbean Islands to Portland, Maine in May is currently the most expensive (average of $416). 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 Islands?

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

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Alternative routes for Caribbean Islands to Portland

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Caribbean Islands to Portland

Discover the top 4 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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$370Average$575FlexibilityNo cancel feeOn-time71%
DeltaCheapest$389Average$406FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$420Average$680FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$428Average$516FlexibilityNo cancel feeOn-time62%

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