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Caribbean Islands

$111+ 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Nov 7 — Nov 141
Fri 11/7
Fri 11/14
1 adult, Economy
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Find 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 October 8, 2025.

This American Airlines deal was found by Cheapflights users on 10/7. 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 11/13:50 pmPWM - SJU
1 stop7h 15mAmerican Airlines
Sat 11/156:25 amSJU - PWM
1 stop6h 48mAmerican Airlines
Deal found 10/7$235
This JetBlue deal was found by Cheapflights users on 10/6. 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.
Wed 10/227:09 amPWM - SJU
1 stop7h 45mJetBlue
Fri 10/242:25 pmSJU - PWM
1 stop8h 39mJetBlue
Deal found 10/6$260
This United Airlines deal was found by Cheapflights users on 10/6. 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 10/226:14 amPWM - SJU
2 stops14h 24mUnited Airlines
Fri 10/244:55 pmSJU - PWM
1 stop7h 04mUnited Airlines
Deal found 10/6$281
This American Airlines deal was found by Cheapflights users on 10/8. 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 11/11:42 pmPWM - SJU
2 stops10h 13mAmerican Airlines
Sat 11/86:25 amSJU - PWM
1 stop17h 29mAmerican Airlines
Deal found 10/8$298
This American Airlines deal was found by Cheapflights users on 10/7. 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.
Fri 11/145:21 pmPWM - PUJ
2 stops20h 12mAmerican Airlines
Mon 11/173:34 pmPUJ - PWM
2 stops21h 12mAmerican Airlines
Deal found 10/7$306
This American Airlines deal was found by Cheapflights users on 10/7. 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.
Sun 12/75:34 amPWM - SJU
2 stops15h 31mAmerican Airlines
Tue 12/168:20 amSJU - PWM
2 stops16h 17mAmerican Airlines
Deal found 10/7$309
This American Airlines deal was found by Cheapflights users on 10/6. 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
Mon 11/36:17 pmSTT - PWM
2 stops18h 29mAmerican Airlines
Deal found 10/6$315
This United Airlines deal was found by Cheapflights users on 10/6. 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 11/96:00 amPWM - NAS
1 stop7h 48mUnited Airlines
Fri 11/142:55 pmNAS - PWM
1 stop8h 22mUnited Airlines
Deal found 10/6$329
This Delta deal was found by Cheapflights users on 10/7. 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.
Sun 11/96:00 amPWM - NAS
1 stop9h 26mDelta
Fri 11/141:19 pmNAS - PWM
1 stop9h 00mDelta
Deal found 10/7$345
This Delta deal was found by Cheapflights users on 10/6. 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 10/222:38 pmPWM - SJU
1 stop9h 18mDelta
Sun 10/267:00 amSJU - PWM
1 stop6h 58mDelta
Deal found 10/6$366
This United Airlines deal was found by Cheapflights users on 10/8. 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 10/236:00 amPWM - SJU
1 stop7h 45mUnited Airlines
Mon 10/277:30 amSJU - PWM
1 stop6h 49mUnited Airlines
Deal found 10/8$376
This Southwest deal was found by Cheapflights users on 10/7. 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.
Sun 12/75:25 pmPWM - SJU
1 stop7h 00mSouthwest
Tue 12/164:40 pmSJU - PWM
1 stop6h 35mSouthwest
Deal found 10/7$382

Cheap 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 October 8, 2025.

Round-trip from

$235
(American Airlines)

One-way from

$111
(United Airlines)

Popular in

December

Cheapest in

January

Average price

$371
From Portland to Caribbean Islands
Search Deals
One-way flight from Portland to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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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 October 8, 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

Mon 1/26

5:35 am-8:50 pm

2 stops14h 15m

San Juan Luis Munoz Marin Intl

Mon 2/2

5:06 pm-10:54 pm

1 stop6h 48m

$235

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 1/24

12:40 pm-11:56 pm

1 stop10h 16m

San Juan Luis Munoz Marin Intl

Sat 2/7

7:00 am-10:54 pm

1 stop16h 54m

$235

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 10/22

7:09 am-2:54 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Fri 10/24

2:25 pm-11:04 pm

1 stop8h 39m

$260

PortlandPunta Cana

PWM - PUJ

PWMPUJ

Portland

Fri 11/14

5:21 pm-2:33 pm

2 stops20h 12m

Punta Cana

Mon 11/17

5:24 pm-11:46 am

2 stops19h 22m

$306

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sun 12/7

5:34 am-10:05 pm

2 stops15h 31m

San Juan Luis Munoz Marin Intl

Tue 12/16

6:25 am-3:05 pm

1 stop9h 40m

$309

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Thu 1/29

5:08 pm-1:10 pm

2 stops19h 02m

Saint Thomas Island Cyril E King

Thu 2/5

6:39 pm-12:06 pm

2 stops18h 27m

$315

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Sat 1/24

3:56 pm-1:10 pm

2 stops20h 14m

Saint Thomas Island Cyril E King

Sat 2/7

3:15 pm-12:05 pm

2 stops21h 50m

$315

PortlandPunta Cana

PWM - PUJ

PWMPUJ

Portland

Tue 2/24

6:30 am-3:53 pm

1 stop8h 23m

Punta Cana

Fri 2/27

5:18 pm-11:49 pm

1 stop7h 31m

$328

PortlandNassau

PWM - NAS

PWMNAS

Portland

Sun 11/9

6:00 am-1:48 pm

1 stop7h 48m

Nassau Intl

Fri 11/14

2:55 pm-11:17 pm

1 stop8h 22m

$329

PortlandNassau

PWM - NAS

PWMNAS

Portland

Sun 11/9

6:00 am-3:26 pm

1 stop9h 26m

Nassau Intl

Fri 11/14

1:19 pm-10:19 pm

1 stop9h 00m

$345

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

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 $84). Flying from Portland, Maine to Caribbean Islands in September is currently the most expensive (average of $147). 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 October 8, 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 49% 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 October 8, 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
8.0
Very good
4,236 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

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
4,236 reviews
Southwest
8.0
Very good
4,236 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

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
7,969 reviews
Southwest
8.0
Very good
4,236 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

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
8,964 reviews
Southwest
8.0
Very good
4,236 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

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
11,042 reviews
Southwest
8.0
Very good
4,236 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

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
2,908 reviews
Southwest
8.0
Very good
4,236 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

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 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 $260, American Airlines can have you in Caribbean Islands from Portland, Maine in 7h 45m. 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?

    $111 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on American Airlines and JetBlue, with prices starting from $111 and $130, 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 - Saint Thomas Island Cyril E King and Portland - Punta Cana.

  • 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 $84). Flying from Portland, Maine to Caribbean Islands in September is currently the most expensive (average of $147). 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 October 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$228FlexibilityNo cancel feeOn-time62%
DeltaCheapest$275Average$517FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$285Average$699FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$301Average$686FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$361Average$602FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$379Average$783FlexibilityNo cancel feeOn-time63%

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