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$91+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PWM
Feb 27 — Mar 61
Thu 2/27
Thu 3/6
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 February 22, 2025.

Round-trip from

$393
(Mytrip)

One-way from

$91
(Priceline)

Popular in

April

Cheapest in

September

Average price

$328
From Caribbean to Portland
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One-way flight from Caribbean to Portland
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($71 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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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 February 22, 2025.

This Delta deal was found by Cheapflights users on 2/21. 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.
Thu 9/47:15 amSJU - PWM
1 stop6h 44mDelta
Mon 9/85:30 amPWM - SJU
1 stop10h 48mDelta
Deal found 2/21$328
This Mytrip deal was found by Cheapflights users on 2/21. 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.
Sat 3/810:35 pmSJU - PWM
1 stop11h 13mFrontier
Wed 3/128:35 pmPWM - SJU
1 stop27h 38mFrontier
Deal found 2/21$393
This American Airlines deal was found by Cheapflights users on 2/21. 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.
Thu 9/45:25 pmSJU - PWM
2 stops18h 29mAmerican Airlines
Mon 9/87:59 amPWM - SJU
1 stop6h 46mAmerican Airlines
Deal found 2/21$397
This JetBlue deal was found by Cheapflights users on 2/21. 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 stop8h 30mJetBlue
Deal found 2/21$429
This United Airlines deal was found by Cheapflights users on 2/21. 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.
Fri 3/72:05 amSJU - PWM
2 stops13h 22mUnited Airlines
Wed 3/126:10 amPWM - SJU
2 stops13h 45mUnited Airlines
Deal found 2/21$445
This Southwest deal was found by Cheapflights users on 2/21. 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 2/21$545

Find flights from Caribbean to Portland within your budget

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 February 22, 2025.

Fly from

Caribbean

Fly to

Portland

Route

Depart

Return

Price

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sat 3/8

10:35 pm-8:48 am

1 stop11h 13m

Portland

Wed 3/12

8:35 pm-12:13 am

1 stop27h 38m

$393

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sat 3/8

6:00 am-3:39 pm

2 stops10h 39m

Portland

Wed 3/12

12:38 pm-11:40 pm

2 stops11h 02m

$421

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-10:50 pm

1 stop8h 30m

$429

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 3/7

2:05 am-2:27 pm

2 stops13h 22m

Portland

Wed 3/12

6:10 am-7:55 pm

2 stops13h 45m

$445

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

$545

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Wed 5/7

3:56 am-8:29 pm

1 stop16h 33m

$91

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Wed 5/7

1:10 am-5:36 pm

3 stops40h 26m

$131

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Mon 3/31

5:35 am-4:55 pm

2 stops11h 20m

$333

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sun 3/30

1:05 am-9:52 am

2 stops32h 47m

$654

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

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.

Travel insights for flights from Caribbean to Portland

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

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 $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 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 February 22, 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 February 22, 2025.
Southwest
8.1
Very good
4,396 reviews

Food

7.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Entertainment

7.6

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
4,396 reviews
Southwest
8.1
Very good
4,396 reviews

Food

7.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Entertainment

7.6

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
3,068 reviews
Southwest
8.1
Very good
4,396 reviews

Food

7.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Entertainment

7.6

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
8,754 reviews
Southwest
8.1
Very good
4,396 reviews

Food

7.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Entertainment

7.6

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
4,396 reviews

Food

7.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Entertainment

7.6

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.

Frontier
6.0
Okay
3,352 reviews
Southwest
8.1
Very good
4,396 reviews

Food

7.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Entertainment

7.6

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 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.

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

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $91. Users have also found prices from $333 and $654 on Southwest and United Airlines, 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, 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 $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?

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 February 22, 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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