HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$109+ 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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 December 12, 2025.

This United Airlines deal was found by Cheapflights users on 12/10. 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.
Thu 12/116:00 amPWM - SJU
2 stops14h 00mUnited Airlines
Thu 12/185:50 pmSJU - PWM
1 stop7h 09mUnited Airlines
Deal found 12/10$296
This American Airlines deal was found by Cheapflights users on 12/11. 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.
Tue 12/163:34 pmPWM - AUA
2 stops22h 14mAmerican Airlines
Tue 12/232:51 pmAUA - PWM
1 stop9h 04mAmerican Airlines
Deal found 12/11$326
This Delta deal was found by Cheapflights users on 12/11. 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.
Wed 12/245:45 amPWM - MBJ
1 stop14h 56mDelta
Wed 12/318:00 amMBJ - PWM
1 stop14h 43mDelta
Deal found 12/11$355
This Southwest deal was found by Cheapflights users on 12/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/113:30 pmPWM - SJU
1 stop6h 50mSouthwest
Thu 12/185:55 pmSJU - PWM
1 stop7h 25mSouthwest
Deal found 12/10$358
This American Airlines deal was found by Cheapflights users on 12/10. 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.
Wed 12/175:17 pmPWM - PUJ
2 stops17h 11mAmerican Airlines
Sat 12/202:27 pmPUJ - PWM
1 stop9h 24mAmerican Airlines
Deal found 12/10$395
This American Airlines deal was found by Cheapflights users on 12/10. 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.
Tue 12/167:00 amPWM - PUJ
1 stop6h 58mAmerican Airlines
Sat 12/202:27 pmPUJ - PWM
1 stop9h 24mAmerican Airlines
Deal found 12/10$397
This Delta deal was found by Cheapflights users on 12/11. 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.
Tue 12/166:08 amPWM - PUJ
1 stop8h 31mDelta
Sat 12/203:38 pmPUJ - PWM
1 stop8h 05mDelta
Deal found 12/11$407
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/135:34 amPWM - SJU
2 stops15h 31mAmerican Airlines
Sun 12/146:25 amSJU - PWM
1 stop17h 35mAmerican Airlines
Deal found 12/10$438
This Delta deal was found by Cheapflights users on 12/11. 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.
Wed 12/176:08 amPWM - PUJ
1 stop8h 31mDelta
Sat 12/203:38 pmPUJ - PWM
1 stop8h 05mDelta
Deal found 12/11$500
This Delta deal was found by Cheapflights users on 12/10. 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.
Mon 12/225:45 amPWM - MBJ
1 stop14h 56mDelta
Mon 12/292:23 pmMBJ - PWM
1 stop8h 20mDelta
Deal found 12/10$504
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/226:41 pmPWM - MBJ
2 stops18h 42mAmerican Airlines
Mon 12/291:25 pmMBJ - PWM
1 stop9h 26mAmerican Airlines
Deal found 12/11$574
This United Airlines deal was found by Cheapflights users on 12/10. 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.
Wed 12/247:30 pmPWM - MBJ
2 stops18h 30mUnited Airlines
Wed 12/313:20 pmMBJ - PWM
2 stops32h 39mUnited Airlines
Deal found 12/10$579

Find flight deals from Portland to Caribbean

Keep the following information in mind while searching for Portland to Caribbean flight deals. Data was last updated December 12, 2025.

Round-trip from

$195
(Trip.com)

One-way from

$109
(Delta)

Popular in

December

Cheapest in

January

Average price

$388
From Portland to Caribbean
Search Deals
One-way flight from Portland to Caribbean
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($25 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 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 12, 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

Mon 2/2

3:12 pm-12:36 am

1 stop8h 24m

San Juan Luis Munoz Marin Intl

Tue 2/10

2:05 am-9:01 am

1 stop7h 56m

$236

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sun 1/18

3:42 pm-6:11 am

2 stops13h 29m

San Juan Luis Munoz Marin Intl

Wed 1/21

2:05 am-2:31 pm

2 stops13h 26m

$249

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 5/5

9:37 am-9:24 pm

2 stops11h 47m

San Juan Luis Munoz Marin Intl

Mon 5/11

1:00 am-10:24 am

2 stops9h 24m

$258

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sat 6/6

6:00 am-1:28 pm

1 stop7h 28m

Simpson Bay Princess Juliana

Sat 6/13

11:45 am-11:36 pm

1 stop11h 51m

$272

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Fri 1/23

2:31 pm-10:22 pm

1 stop6h 51m

San Juan Luis Munoz Marin Intl

Fri 1/30

2:05 am-9:01 am

1 stop7h 56m

$285

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 1/19

5:20 am-5:03 pm

2 stops10h 43m

San Juan Luis Munoz Marin Intl

Thu 1/22

1:24 pm-11:43 pm

2 stops11h 19m

$291

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Fri 1/30

6:00 am-2:31 pm

1 stop7h 31m

Simpson Bay Princess Juliana

Mon 2/2

2:42 pm-10:54 pm

1 stop9h 12m

$293

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Fri 1/9

6:00 am-2:31 pm

1 stop7h 31m

Simpson Bay Princess Juliana

Tue 1/13

3:09 pm-12:06 pm

2 stops21h 57m

$298

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Thu 1/8

12:46 pm-12:58 pm

2 stops23h 12m

Simpson Bay Princess Juliana

Tue 1/13

3:31 pm-12:06 pm

2 stops21h 35m

$298

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

Sat 3/14

6:29 pm-3:43 pm

2 stops21h 14m

Oranjestad Reina Beatrix

Wed 3/18

5:13 pm-10:23 am

2 stops17h 10m

$304

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 59 results
1
2
3
...
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, January is the cheapest month in which you can book a flight from Portland, Maine to Caribbean (average of $88). Flying from Portland, Maine to Caribbean 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 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 December 12, 2025.

It’s optimal to fly from Portland, Maine to Caribbean in the evening. By choosing this option you can save up to 60% on the cost of your flight, compared to a flight in the morning.

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 December 12, 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
7.9
Good
4,253 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

7.9

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
4,253 reviews
Southwest
7.9
Good
4,253 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

7.9

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
8,007 reviews
Southwest
7.9
Good
4,253 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

7.9

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
9,095 reviews
Southwest
7.9
Good
4,253 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

7.9

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
11,050 reviews
Southwest
7.9
Good
4,253 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

7.9

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
2,899 reviews
Southwest
7.9
Good
4,253 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

7.9

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. 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 28m. There are 1817 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 $86 on Frontier. Other airlines that offer cheap prices include United Airlines from $142 and American Airlines from $150 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 - Simpson Bay Princess Juliana and Portland - George Town Owen Roberts Intl.

  • 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, January is the cheapest month in which you can book a flight from Portland, Maine to Caribbean (average of $88). Flying from Portland, Maine to Caribbean 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
Boston to Fort Lauderdale flights
Boston to Miami flights
Boston to Los Angeles flights
Boston to Orlando flights
Boston to Cancún flights
Boston to Las Vegas flights
Boston to Luis Munoz Marin Intl flights
Boston to Dallas/Fort Worth flights
Boston to Tampa flights
Boston to Heathrow flights
Boston to Fort Myers flights
Boston to Denver flights
Boston to San Francisco flights
Boston to West Palm Beach flights
Boston to Atlanta flights
Boston to Sky Harbor Intl flights
Boston to Baltimore flights
Boston to Oranjestad flights
Boston to Charles de Gaulle flights
Boston to Salt Lake City flights
Boston to Santo Domingo flights
Boston to Hobby flights
Boston to New Orleans flights
Boston to Leonardo da Vinci/Fiumicino flights
Boston to Narita flights
Boston to Seattle flights
Boston to O'Hare Intl flights
Boston to Dulles Intl flights
Boston to Newark flights
Boston to Punta Cana flights
Boston to George Bush Intcntl flights
Boston to San Diego flights
Boston to Dublin flights
Boston to LaGuardia flights
Boston to Gatwick flights
Boston to Austin flights
Boston to Sarasota flights
Boston to Reagan-National flights
Boston to Mexico City flights
Boston to Lisbon flights
Boston to Charlotte flights
Boston to John F Kennedy Intl flights
Boston to London City flights
Boston to Nashville flights
Boston to Cozumel flights
Boston to Haneda flights
Boston to Orly flights
Boston to Charleston flights
Boston to Athens flights
Boston to Saint Thomas Island flights

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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$228FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$237Average$559FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$249Average$639FlexibilityNo cancel feeOn-time69%
DeltaCheapest$274Average$495FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$296Average$616FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$736FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.