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Caribbean Islands

$106+ Cheap flights from Portland, ME (PWM) to Caribbean Islands

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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Portland to Caribbean Islands

Cheapest flights from Portland to Caribbean Islands
Explore the most affordable flight options available from Portland to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This Delta deal was found by Cheapflights users on 12/16. 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.
Tue 12/235:45 amPWM - GCM
1 stop6h 51mDelta
Fri 12/263:42 pmGCM - PWM
1 stop7h 01mDelta
Deal found 12/16$328
This United Airlines deal was found by Cheapflights users on 12/15. 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 12/185:30 amPWM - PUJ
1 stop10h 55mUnited Airlines
Wed 12/2412:56 pmPUJ - PWM
1 stop12h 03mUnited Airlines
Deal found 12/15$375
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/176:40 pmPWM - PUJ
1 stop16h 01mAmerican Airlines
Sat 12/204:44 pmPUJ - PWM
1 stop7h 11mAmerican Airlines
Deal found 12/16$378
This Delta deal was found by Cheapflights users on 12/16. 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 12/315:45 amPWM - NAS
1 stop9h 18mDelta
Tue 1/61:20 pmNAS - PWM
1 stop11h 00mDelta
Deal found 12/16$393
This Delta deal was found by Cheapflights users on 12/16. 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 12/245:45 amPWM - MBJ
1 stop14h 56mDelta
Wed 12/318:00 amMBJ - PWM
1 stop14h 43mDelta
Deal found 12/16$407
This Delta deal was found by Cheapflights users on 12/15. 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 12/176:15 amPWM - SJU
1 stop10h 05mDelta
Fri 12/191:55 pmSJU - PWM
1 stop9h 28mDelta
Deal found 12/15$418
This Delta deal was found by Cheapflights users on 12/15. 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 12/176:08 amPWM - PUJ
1 stop8h 31mDelta
Sat 12/202:06 pmPUJ - PWM
1 stop9h 37mDelta
Deal found 12/15$427
This American Airlines deal was found by Cheapflights users on 12/15. 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.
Tue 12/165:17 pmPWM - PUJ
2 stops20h 41mAmerican Airlines
Sat 12/204:44 pmPUJ - PWM
1 stop7h 11mAmerican Airlines
Deal found 12/15$431
This United Airlines deal was found by Cheapflights users on 12/17. 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 12/247:30 pmPWM - SXM
1 stop17h 20mUnited Airlines
Fri 12/264:55 pmSXM - PWM
1 stop8h 04mUnited Airlines
Deal found 12/17$443
This Delta deal was found by Cheapflights users on 12/17. 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 12/186:08 amPWM - MBJ
1 stop6h 56mDelta
Thu 12/253:38 pmMBJ - PWM
1 stop7h 05mDelta
Deal found 12/17$455
This United Airlines deal was found by Cheapflights users on 12/16. 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 12/237:30 pmPWM - GCM
2 stops18h 15mUnited Airlines
Fri 12/262:25 pmGCM - PWM
1 stop8h 57mUnited Airlines
Deal found 12/16$456
This Delta deal was found by Cheapflights users on 12/16. 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 12/255:45 amPWM - STT
1 stop8h 20mDelta
Wed 12/313:06 pmSTT - PWM
1 stop8h 37mDelta
Deal found 12/16$472

Find flight deals from Portland to Caribbean Islands

Keep the following information in mind while searching for Portland to Caribbean Islands flight deals. Data was last updated December 18, 2025.

Round-trip from

$195
(United Airlines)

One-way from

$106
(United Airlines)

Popular in

December

Cheapest in

January

Average price

$386
From Portland to Caribbean Islands
Search Deals
One-way flight from Portland to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Caribbean Islands 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 December 18, 2025.
Use the filters below to find and compare flights from Portland to Caribbean Islands that are best for you.

Fly from

Portland

Fly to

Caribbean Islands

Route

Depart

Return

Price

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 1/27

6:00 am-9:00 pm

2 stops14h 00m

San Juan Luis Munoz Marin Intl

Fri 1/30

2:05 am-2:39 pm

2 stops13h 34m

$195

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 3/4

6:00 am-2:40 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Mon 3/9

1:05 am-3:14 pm

2 stops14h 09m

$244

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 3/2

4:35 pm-1:15 am

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Wed 3/11

5:05 am-3:40 pm

1 stop10h 35m

$274

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 2/3

6:17 am-4:50 pm

1 stop9h 33m

San Juan Luis Munoz Marin Intl

Fri 2/27

6:02 pm-12:18 am

1 stop7h 16m

$275

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 2/3

6:17 am-4:50 pm

1 stop9h 33m

San Juan Luis Munoz Marin Intl

Thu 2/26

7:00 am-1:43 pm

1 stop7h 43m

$275

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sun 2/1

6:00 am-4:50 pm

1 stop9h 50m

San Juan Luis Munoz Marin Intl

Thu 2/26

7:00 am-1:43 pm

1 stop7h 43m

$275

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 2/4

5:30 am-5:17 pm

1 stop10h 47m

San Juan Luis Munoz Marin Intl

Fri 2/27

6:02 pm-12:18 am

1 stop7h 16m

$275

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sun 2/1

6:00 am-4:50 pm

1 stop9h 50m

San Juan Luis Munoz Marin Intl

Fri 2/27

2:16 pm-12:18 am

1 stop11h 02m

$275

PortlandPunta Cana

PWM - PUJ

PWMPUJ

Portland

Wed 4/15

6:00 am-12:59 pm

1 stop6h 59m

Punta Cana

Wed 4/22

2:05 pm-11:36 pm

1 stop9h 31m

$290

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Thu 1/29

6:16 am-4:50 pm

1 stop9h 34m

San Juan Luis Munoz Marin Intl

Thu 2/26

7:00 am-1:43 pm

1 stop7h 43m

$301

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 60 results
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Best time to book a flight from Portland to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Portland 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 Portland to Caribbean Islands

What is the cheapest month to book a flight from Portland, Maine to Caribbean Islands?

Currently, January is the cheapest month in which you can book a flight from Portland, Maine to Caribbean Islands (average of $88). Flying from Portland, Maine to Caribbean Islands in November is currently the most expensive (average of $177). 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 PWM to EPX?

Find hourly flight availability from Portland to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2025.

A simple way to save on the total cost of your ticket is to fly from Portland, Maine to Caribbean Islands in the evening. If you’re flexible enough to do this you can expect to save up to 60% on your trip compared to booking a flight in the morning.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Caribbean Islands. Reviews last updated December 18, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Portland to Caribbean Islands by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,250 reviews

Overall

7.9

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Overall

7.9

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,005 reviews
Southwest
7.9
Good
4,250 reviews

Overall

7.9

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,091 reviews
Southwest
7.9
Good
4,250 reviews

Overall

7.9

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,054 reviews
Southwest
7.9
Good
4,250 reviews

Overall

7.9

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
JetBlue
7.2
Good
2,897 reviews
Southwest
7.9
Good
4,250 reviews

Overall

7.9

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Portland to Caribbean Islands. 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 from for flights from Portland to Caribbean Islands?

    If you book a flight to Caribbean Islands from Portland, you will be flying from Portland, which is the city’s only airport. Portland (PWM) is located 2.9 mi from the center of Portland.

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

    For as low as $274, United Airlines can have you in Caribbean Islands from Portland, Maine in 7h 40m. Portland, Maine and Caribbean Islands are separated by a distance of 1758 mi. This flight may include one or multiple stops.

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

    $86 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on United Airlines and American Airlines, with prices starting from $142 and $150, respectively.

  • What are the most popular routes from Portland, Maine to Caribbean Islands?

    The most popular flight routes from Portland, Maine to Caribbean Islands are Portland - San Juan Luis Munoz Marin Intl, Portland - Simpson Bay Princess Juliana and Portland - Saint Thomas Island Cyril E King.

  • Can I find deals for flights from Portland to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Portland to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Caribbean Islands.

  • Can I find deals for business class flights from Portland to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Portland to Caribbean Islands 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 Portland, Maine to Caribbean Islands?

    Currently, January is the cheapest month in which you can book a flight from Portland, Maine to Caribbean Islands (average of $88). Flying from Portland, Maine to Caribbean Islands in November is currently the most expensive (average of $177). 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

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Top 6 airlines flying from Portland to Caribbean Islands

Discover the top 6 airlines that operate flights from Portland to Caribbean Islands. 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$228FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$237Average$566FlexibilityNo cancel feeOn-time62%
DeltaCheapest$274Average$491FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$296Average$619FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$302Average$635FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$315Average$739FlexibilityNo cancel feeOn-time63%

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