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Caribbean Islands

$132+ 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 8/9. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
jul. 6 — jul. 131
dom. 7/6
dom. 7/13
1 adult, Economy
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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 julio 1, 2025.

Round-trip from

$275
(Delta)

One-way from

$132
(Priceline)

Popular in

December

Cheapest in

September

Average price

$340
From Portland to Caribbean Islands
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One-way flight from Portland to Caribbean Islands
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Highest demand for flights based on searches. 7% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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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 julio 1, 2025.

This Delta deal was found by Cheapflights users on 7/1. 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.
vie. 10/36:33 amPWM - SJU
1 stop9h 47mDelta
dom. 10/51:37 pmSJU - PWM
1 stop10h 57mDelta
Deal found 7/1$275
This JetBlue deal was found by Cheapflights users on 6/30. 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.
mié. 8/66:10 amPWM - SJU
1 stop6h 40mJetBlue
dom. 8/102:58 pmSJU - PWM
1 stop9h 19mJetBlue
Deal found 6/30$288
This American Airlines deal was found by Cheapflights users on 7/1. 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.
vie. 10/37:05 amPWM - SJU
2 stops16h 32mAmerican Airlines
lun. 10/67:10 amSJU - PWM
1 stop15h 52mAmerican Airlines
Deal found 7/1$291
This United Airlines deal was found by Cheapflights users on 6/30. 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.
vie. 9/266:00 amPWM - SJU
1 stop7h 45mUnited Airlines
dom. 9/281:05 amSJU - PWM
1 stop8h 06mUnited Airlines
Deal found 6/30$341
This American Airlines deal was found by Cheapflights users on 6/29. 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.
mié. 9/246:00 amPWM - AUA
2 stops9h 27mAmerican Airlines
mar. 9/304:50 pmAUA - PWM
2 stops20h 17mAmerican Airlines
Deal found 6/29$350
This Delta deal was found by Cheapflights users on 6/29. 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.
dom. 11/95:40 amPWM - MBJ
1 stop10h 53mDelta
vie. 11/142:07 pmMBJ - PWM
1 stop9h 24mDelta
Deal found 6/29$371
This American Airlines deal was found by Cheapflights users on 6/29. 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.
dom. 11/94:18 pmPWM - MBJ
2 stops19h 32mAmerican Airlines
vie. 11/144:05 pmMBJ - PWM
2 stops19h 58mAmerican Airlines
Deal found 6/29$375
This Delta deal was found by Cheapflights users on 7/1. 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.
mar. 9/236:00 amPWM - NAS
1 stop7h 49mDelta
dom. 9/281:15 pmNAS - PWM
1 stop10h 56mDelta
Deal found 7/1$384
This American Airlines deal was found by Cheapflights users on 6/29. 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.
lun. 10/207:44 amPWM - PUJ
1 stop6h 57mAmerican Airlines
vie. 10/243:52 pmPUJ - PWM
1 stop6h 56mAmerican Airlines
Deal found 6/29$385
This American Airlines deal was found by Cheapflights users on 7/1. 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.
mar. 9/236:00 amPWM - NAS
2 stops7h 15mAmerican Airlines
dom. 9/286:40 pmNAS - PWM
2 stops17h 06mAmerican Airlines
Deal found 7/1$393
This Southwest deal was found by Cheapflights users on 7/1. 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.
vie. 10/35:50 amPWM - SJU
2 stops8h 55mSouthwest
dom. 10/55:40 pmSJU - PWM
1 stop6h 45mSouthwest
Deal found 7/1$411
This Delta deal was found by Cheapflights users on 6/30. 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.
mar. 12/165:30 amPWM - AUA
1 stop7h 30mDelta
mar. 12/233:10 pmAUA - PWM
1 stop9h 21mDelta
Deal found 6/30$427

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 julio 1, 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

vie. 10/3

6:33 am-4:20 pm

1 stop9h 47m

San Juan Luis Munoz Marin Intl

dom. 10/5

1:37 pm-12:34 am

1 stop10h 57m

$275

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

mié. 8/6

6:10 am-12:50 pm

1 stop6h 40m

San Juan Luis Munoz Marin Intl

dom. 8/10

2:58 pm-12:17 am

1 stop9h 19m

$288

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

vie. 10/3

7:05 am-11:37 pm

2 stops16h 32m

San Juan Luis Munoz Marin Intl

lun. 10/6

7:10 am-11:02 pm

1 stop15h 52m

$291

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

vie. 9/26

6:00 am-1:45 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

dom. 9/28

1:05 am-9:11 am

1 stop8h 06m

$341

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

mié. 9/24

6:00 am-3:27 pm

2 stops9h 27m

Oranjestad Reina Beatrix

mar. 9/30

4:50 pm-1:07 pm

2 stops20h 17m

$350

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

vie. 10/3

5:50 am-2:45 pm

2 stops8h 55m

San Juan Luis Munoz Marin Intl

dom. 10/5

5:40 pm-12:25 am

1 stop6h 45m

$411

PortlandNassau

PWM - NAS

PWMNAS

Portland

jue. 11/13

5:40 am-3:25 pm

1 stop9h 45m

Nassau Intl

lun. 11/17

1:25 pm-11:31 pm

1 stop10h 06m

$419

PortlandNassau

PWM - NAS

PWMNAS

Portland

jue. 8/14

6:00 am-5:35 pm

2 stops11h 35m

Nassau Intl

jue. 8/21

12:44 pm-10:59 pm

2 stops10h 15m

$423

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

mar. 12/16

5:30 am-2:00 pm

1 stop7h 30m

Oranjestad Reina Beatrix

mar. 12/23

3:10 pm-11:31 pm

1 stop9h 21m

$427

PortlandPunta Cana

PWM - PUJ

PWMPUJ

Portland

vie. 9/19

5:20 pm-11:59 am

2 stops18h 39m

Punta Cana

mar. 9/23

4:25 pm-12:29 pm

2 stops20h 04m

$430

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 42 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, September is the cheapest month in which you can book a flight from Portland, Maine to Caribbean Islands (average of $254). Flying from Portland, Maine to Caribbean Islands 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 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 julio 1, 2025.

When flying from Portland, Maine to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 julio 1, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and LATAM 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
4,275 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,275 reviews
Southwest
8.0
Very good
4,275 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,974 reviews
Southwest
8.0
Very good
4,275 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
LATAM Airlines
7.5
Good
1,805 reviews
Southwest
8.0
Very good
4,275 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Copa Airlines
7.5
Good
1,465 reviews
Southwest
8.0
Very good
4,275 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,858 reviews
Southwest
8.0
Very good
4,275 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

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

    $132 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on American Airlines and Delta, with prices starting from $163 and $267, 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 - Punta Cana, Portland - San Juan Luis Munoz Marin Intl 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, September is the cheapest month in which you can book a flight from Portland, Maine to Caribbean Islands (average of $254). Flying from Portland, Maine to Caribbean Islands 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 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 julio 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$229FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$214Average$551FlexibilityNo cancel feeOn-time62%
DeltaCheapest$274Average$520FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$285Average$687FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$322Average$619FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$401Average$752FlexibilityNo cancel feeOn-time63%

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