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$144+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PWM
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Round-trip from

$284
(Booking.com)

One-way from

$144
(Mytrip)
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 February 20, 2025.

This Booking.com deal was found by Cheapflights users on 2/19. 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.
Sat 4/199:35 pmSJU - PWM
1 stop11h 37mFrontier
Sat 4/269:09 pmPWM - SJU
1 stop29h 40mFrontier
Deal found 2/19$284
This Delta deal was found by Cheapflights users on 2/19. 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 4/43:34 pmSJU - PWM
1 stop8h 25mDelta
Sun 4/135:30 amPWM - SJU
1 stop10h 33mDelta
Deal found 2/19$328
This JetBlue deal was found by Cheapflights users on 2/20. 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.
Fri 8/151:20 pmSJU - PWM
1 stop10h 17mJetBlue
Sat 8/232:20 pmPWM - SJU
1 stop10h 34mJetBlue
Deal found 2/20$429
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Sat 4/195:30 amSJU - PWM
1 stop17h 19mAmerican Airlines
Sat 4/266:00 amPWM - SJU
2 stops14h 28mAmerican Airlines
Deal found 2/19$463
This Southwest deal was found by Cheapflights users on 2/20. 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 8/155:50 amSJU - PWM
1 stop8h 45mSouthwest
Sat 8/235:45 amPWM - SJU
2 stops10h 40mSouthwest
Deal found 2/20$525
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/252:06 amSJU - PWM
1 stop9h 02mMultiple Airlines
Wed 6/412:53 pmPWM - SJU
1 stop12h 18mMultiple Airlines
Deal found 2/20$536
This United Airlines deal was found by Cheapflights users on 2/20. 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 5/251:05 amSJU - PWM
2 stops9h 22mUnited Airlines
Wed 6/46:00 amPWM - SJU
1 stop7h 45mUnited Airlines
Deal found 2/20$571

Find flights from Caribbean Islands to Portland within your budget

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 February 20, 2025.

Fly from

Caribbean Islands

Fly to

Portland

Route

Depart

Return

Price

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sat 4/19

9:35 pm-9:12 am

1 stop11h 37m

Portland

Sat 4/26

9:09 pm-2:49 am

1 stop29h 40m

$284

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 4/4

3:34 pm-11:59 pm

1 stop8h 25m

Portland

Sun 4/13

5:30 am-4:03 pm

1 stop10h 33m

$328

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 8/15

1:20 pm-11:37 pm

1 stop10h 17m

Portland

Sat 8/23

2:20 pm-12:54 am

1 stop10h 34m

$429

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sat 4/19

5:30 am-10:49 pm

1 stop17h 19m

Portland

Sat 4/26

6:00 am-8:28 pm

2 stops14h 28m

$463

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 8/15

5:50 am-2:35 pm

1 stop8h 45m

Portland

Sat 8/23

5:45 am-4:25 pm

2 stops10h 40m

$525

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sun 5/25

2:06 am-11:08 am

1 stop9h 02m

Portland

Wed 6/4

12:53 pm-1:11 am

1 stop12h 18m

$536

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sun 5/25

1:05 am-10:27 am

2 stops9h 22m

Portland

Wed 6/4

6:00 am-1:45 pm

1 stop7h 45m

$571

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Tue 3/4

6:00 am-7:41 pm

3 stops38h 41m

$144

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Mon 3/31

5:35 am-4:43 pm

1 stop11h 08m

$146

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Mon 3/3

2:05 am-2:32 pm

2 stops13h 27m

$218

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 11 results
1
2

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.

Travel insights for flights from Caribbean Islands to Portland

Get recent, data-driven insights about flights from Caribbean Islands to Portland including ideal travel times, pricing trends, and more.

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 April is currently the most expensive (average of $498). 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 February 20, 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 February 20, 2025.
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $146. United Airlines flights start at $218 while deals on Southwest start at $333 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 April is currently the most expensive (average of $498). 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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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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$413Average$575FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$420Average$680FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$428Average$515FlexibilityNo cancel feeOn-time62%
DeltaCheapest$524Average$652FlexibilityNo cancel feeOn-timeN/A
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