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$118+ Cheap flights from Portland, ME (PWM) to Caribbean

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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Portland to Caribbean

Keep the following information in mind while searching for Portland to Caribbean flight deals. Data was last updated September 11, 2025.

Round-trip from

$235
(American Airlines)

One-way from

$118
(Southwest)

Popular in

December

Cheapest in

September

Average price

$285
From Portland to Caribbean
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One-way flight from Portland to Caribbean
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Highest demand for flights based on searches. 5% potential increase in price ($28 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Portland to Caribbean

Cheapest flights from Portland to Caribbean
Explore the most affordable flight options available from Portland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This American Airlines deal was found by Cheapflights users on 9/9. 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 10/256:00 amPWM - SJU
1 stop17h 05mAmerican Airlines
Sat 11/15:30 amSJU - PWM
1 stop15h 28mAmerican Airlines
Deal found 9/9$235
This Delta deal was found by Cheapflights users on 9/11. 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 9/266:33 amPWM - SJU
1 stop9h 47mDelta
Tue 9/306:00 pmSJU - PWM
1 stop6h 34mDelta
Deal found 9/11$281
This American Airlines deal was found by Cheapflights users on 9/11. 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 10/257:44 amPWM - SJU
2 stops16h 10mAmerican Airlines
Fri 10/315:02 pmSJU - PWM
2 stops18h 52mAmerican Airlines
Deal found 9/11$295
This American Airlines deal was found by Cheapflights users on 9/11. 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 10/227:44 amPWM - SJU
2 stops14h 26mAmerican Airlines
Sun 10/265:30 amSJU - PWM
1 stop15h 17mAmerican Airlines
Deal found 9/11$303
This American Airlines deal was found by Cheapflights users on 9/10. 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 12/65:17 pmPWM - SJU
2 stops17h 42mAmerican Airlines
Mon 12/156:25 amSJU - PWM
1 stop12h 48mAmerican Airlines
Deal found 9/10$305
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Mon 10/275:59 pmPWM - STT
1 stop18h 01mAmerican Airlines
Wed 11/56:17 pmSTT - PWM
2 stops23h 20mAmerican Airlines
Deal found 9/11$315
This United Airlines deal was found by Cheapflights users on 9/11. 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 9/263:45 pmPWM - SJU
1 stop8h 12mUnited Airlines
Mon 9/291:05 amSJU - PWM
1 stop8h 06mUnited Airlines
Deal found 9/11$317
This Delta deal was found by Cheapflights users on 9/10. 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 9/196:33 amPWM - SJU
1 stop9h 47mDelta
Fri 9/266:00 pmSJU - PWM
1 stop6h 34mDelta
Deal found 9/10$321
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Sat 10/253:45 pmPWM - SJU
1 stop8h 12mUnited Airlines
Fri 10/311:05 amSJU - PWM
2 stops13h 07mUnited Airlines
Deal found 9/10$327
This Delta deal was found by Cheapflights users on 9/11. 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.
Sat 12/66:00 amPWM - NAS
1 stop7h 27mDelta
Sat 12/132:55 pmNAS - PWM
1 stop7h 22mDelta
Deal found 9/11$347
This JetBlue deal was found by Cheapflights users on 9/11. 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 9/197:30 amPWM - SJU
1 stop9h 13mJetBlue
Fri 9/262:25 pmSJU - PWM
1 stop7h 42mJetBlue
Deal found 9/11$349
This Delta deal was found by Cheapflights users on 9/11. 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 12/56:00 amPWM - NAS
1 stop9h 28mDelta
Sat 12/132:40 pmNAS - PWM
1 stop6h 11mDelta
Deal found 9/11$357

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Caribbean 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 September 11, 2025.
Use the filters below to find and compare flights from Portland to Caribbean that are best for you.

Fly from

Portland

Fly to

Caribbean

Route

Depart

Return

Price

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 10/25

6:00 am-11:05 pm

1 stop17h 05m

San Juan Luis Munoz Marin Intl

Sat 11/1

5:30 am-4:27 pm

2 stops10h 57m

$235

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Mon 11/10

5:21 pm-4:57 pm

2 stops22h 36m

Saint Thomas Island Cyril E King

Sat 11/15

6:17 pm-11:46 am

2 stops18h 29m

$315

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Sat 1/24

2:24 pm-12:10 pm

2 stops20h 46m

Saint Thomas Island Cyril E King

Sat 2/7

4:35 pm-12:09 pm

2 stops20h 34m

$315

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Fri 9/26

3:45 pm-11:57 pm

1 stop8h 12m

San Juan Luis Munoz Marin Intl

Mon 9/29

1:05 am-9:11 am

1 stop8h 06m

$317

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Sun 1/18

2:24 pm-12:10 pm

2 stops20h 46m

Saint Thomas Island Cyril E King

Tue 3/17

3:30 pm-12:00 pm

2 stops20h 30m

$340

PortlandNassau

PWM - NAS

PWMNAS

Portland

Sat 12/6

6:00 am-1:27 pm

1 stop7h 27m

Nassau Intl

Sat 12/13

2:55 pm-10:17 pm

1 stop7h 22m

$347

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 10/25

6:00 am-1:45 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Fri 10/31

1:05 am-2:12 pm

2 stops13h 07m

$353

PortlandNassau

PWM - NAS

PWMNAS

Portland

Fri 12/5

6:00 am-3:28 pm

1 stop9h 28m

Nassau Intl

Sat 12/13

2:40 pm-8:51 pm

1 stop6h 11m

$357

PortlandNassau

PWM - NAS

PWMNAS

Portland

Mon 12/8

5:46 am-11:06 am

1 stop5h 20m

Nassau Intl

Mon 12/15

1:13 pm-9:37 pm

1 stop8h 24m

$357

PortlandNassau

PWM - NAS

PWMNAS

Portland

Sun 12/7

6:00 am-3:28 pm

1 stop9h 28m

Nassau Intl

Sat 12/13

4:53 pm-4:06 pm

2 stops23h 13m

$361

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 60 results
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6

Best time to book a flight from Portland to Caribbean

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

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

Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Caribbean (average of $254). Flying from Portland, Maine to Caribbean in June is currently the most expensive (average of $339). 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 CB?

Find hourly flight availability from Portland to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Portland, Maine to Caribbean as you normally would.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated September 11, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Portland to Caribbean. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,913 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

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

    Portland (PWM) is the airport you will fly out of if you book a flight from Portland to Caribbean. It is only a 2.9 mi journey to Portland (PWM) from Portland’s city center.

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

    Departing from Portland, Maine to Caribbean will take you 7h 27m. There are 1346 mi between Portland, Maine and Caribbean. Both multi-stop and nonstop flights can be found to your destination and back.

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

    One-way options have recently been found by users for as low as $118 on Southwest. Other airlines that offer cheap prices include Delta from $138 and American Airlines from $177 one-way.

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

    The most popular flight routes from Portland, Maine to Caribbean are Portland - San Juan Luis Munoz Marin Intl, Portland - Saint Thomas Island Cyril E King and Portland - Punta Cana.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Portland to Caribbean 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?

    Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Caribbean (average of $254). Flying from Portland, Maine to Caribbean in June is currently the most expensive (average of $339). 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

Discover the top 6 airlines that operate flights from Portland to Caribbean. 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$228FlexibilityNo cancel feeOn-time62%
DeltaCheapest$274Average$514FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$281Average$638FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$285Average$693FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$297Average$601FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$401Average$752FlexibilityNo cancel feeOn-time63%

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