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$149+ 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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Apr 30 — May 71
Wed 4/30
Wed 5/7
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 April 25, 2025.

Round-trip from

$275
(Delta)

One-way from

$149
(Frontier)

Popular in

April

Cheapest in

September

Average price

$629
From Portland to Caribbean
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One-way flight from Portland to Caribbean
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($47 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 25, 2025.

This Delta deal was found by Cheapflights users on 4/24. 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 5/286:35 amPWM - SJU
1 stop10h 09mDelta
Wed 6/41:12 pmSJU - PWM
1 stop11h 02mDelta
Deal found 4/24$275
This American Airlines deal was found by Cheapflights users on 4/24. 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 5/286:00 amPWM - SJU
2 stops14h 09mAmerican Airlines
Wed 6/41:35 pmSJU - PWM
1 stop9h 10mAmerican Airlines
Deal found 4/24$388
This American Airlines deal was found by Cheapflights users on 4/25. 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 5/95:24 pmPWM - MBJ
2 stops19h 06mAmerican Airlines
Sun 5/112:41 pmMBJ - PWM
2 stops18h 39mAmerican Airlines
Deal found 4/25$416
This JetBlue deal was found by Cheapflights users on 4/25. 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 5/167:12 amPWM - SDQ
1 stop9h 13mJetBlue
Sat 5/173:09 amSDQ - PWM
1 stop11h 31mJetBlue
Deal found 4/25$421
This Delta deal was found by Cheapflights users on 4/25. 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 6/96:00 amPWM - NAS
1 stop7h 43mDelta
Mon 6/165:18 pmNAS - PWM
1 stop7h 08mDelta
Deal found 4/25$421
This American Airlines deal was found by Cheapflights users on 4/25. 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.
Thu 10/235:54 amPWM - AUA
1 stop7h 01mAmerican Airlines
Thu 10/305:20 pmAUA - PWM
1 stop18h 01mAmerican Airlines
Deal found 4/25$429
This American Airlines deal was found by Cheapflights users on 4/24. 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 10/154:09 pmPWM - STT
2 stops20h 41mAmerican Airlines
Wed 10/225:15 pmSTT - PWM
2 stops18h 44mAmerican Airlines
Deal found 4/24$439
This Delta deal was found by Cheapflights users on 4/24. 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 5/95:30 amPWM - PUJ
1 stop7h 52mDelta
Tue 5/131:45 pmPUJ - PWM
1 stop10h 29mDelta
Deal found 4/24$441
This Delta deal was found by Cheapflights users on 4/25. 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 5/162:30 pmPWM - SDQ
1 stop9h 49mDelta
Mon 5/192:28 pmSDQ - PWM
1 stop9h 46mDelta
Deal found 4/25$441
This United Airlines deal was found by Cheapflights users on 4/24. 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 5/95:30 amPWM - PUJ
2 stops10h 05mUnited Airlines
Tue 5/131:50 pmPUJ - PWM
2 stops20h 06mUnited Airlines
Deal found 4/24$445
This American Airlines deal was found by Cheapflights users on 4/24. 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.
Thu 5/84:01 pmPWM - PUJ
1 stop20h 24mAmerican Airlines
Tue 5/132:12 pmPUJ - PWM
1 stop8h 53mAmerican Airlines
Deal found 4/24$448
This JetBlue deal was found by Cheapflights users on 4/25. 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 - PUJ
1 stop9h 44mJetBlue
Tue 9/2311:30 amPUJ - PWM
1 stop10h 29mJetBlue
Deal found 4/25$458

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 April 25, 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

Wed 5/28

6:35 am-4:44 pm

1 stop10h 09m

San Juan Luis Munoz Marin Intl

Wed 6/4

1:12 pm-12:14 am

1 stop11h 02m

$275

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 5/28

6:00 am-8:09 pm

2 stops14h 09m

San Juan Luis Munoz Marin Intl

Wed 6/4

1:35 pm-10:45 pm

1 stop9h 10m

$388

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Fri 5/9

5:24 pm-11:30 am

2 stops19h 06m

Montego Bay Sangster Intl

Sun 5/11

2:41 pm-10:20 am

2 stops18h 39m

$416

PortlandSanto Domingo

PWM - SDQ

PWMSDQ

Portland

Fri 5/16

7:12 am-4:25 pm

1 stop9h 13m

Santo Domingo Las Americas

Sat 5/17

3:09 am-2:40 pm

1 stop11h 31m

$421

PortlandNassau

PWM - NAS

PWMNAS

Portland

Mon 6/9

6:00 am-1:43 pm

1 stop7h 43m

Nassau Intl

Mon 6/16

5:18 pm-12:26 am

1 stop7h 08m

$421

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

Fri 9/12

6:46 pm-3:45 pm

2 stops20h 59m

Oranjestad Reina Beatrix

Mon 9/22

3:30 pm-11:10 am

2 stops19h 40m

$434

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Wed 10/15

4:09 pm-12:50 pm

2 stops20h 41m

Saint Thomas Island Cyril E King

Wed 10/22

5:15 pm-11:59 am

2 stops18h 44m

$439

PortlandPunta Cana

PWM - PUJ

PWMPUJ

Portland

Fri 5/9

5:30 am-2:45 pm

1 stop9h 15m

Punta Cana

Wed 5/14

1:05 pm-11:59 pm

1 stop10h 54m

$441

PortlandSanto Domingo

PWM - SDQ

PWMSDQ

Portland

Fri 5/16

2:30 pm-12:19 am

1 stop9h 49m

Santo Domingo Las Americas

Mon 5/19

2:28 pm-12:14 am

1 stop9h 46m

$441

PortlandPunta Cana

PWM - PUJ

PWMPUJ

Portland

Fri 5/9

5:30 am-3:35 pm

2 stops10h 05m

Punta Cana

Tue 5/13

1:50 pm-9:56 am

2 stops20h 06m

$445

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/25

Showing 1-10 of 36 results
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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 December is currently the most expensive (average of $336). 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 April 25, 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.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 April 25, 2025.
Southwest
8.0
Very good
4,289 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,289 reviews
Southwest
8.0
Very good
4,289 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,289 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
LATAM Airlines
7.5
Good
1,767 reviews
Southwest
8.0
Very good
4,289 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,685 reviews
Southwest
8.0
Very good
4,289 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,922 reviews
Southwest
8.0
Very good
4,289 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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.

  • 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 $149 on Frontier. Other airlines that offer cheap prices include Delta from $218 and United Airlines from $263 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 - Oranjestad Reina Beatrix, Portland - San Juan Luis Munoz Marin Intl and Portland - Nassau 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, 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 December is currently the most expensive (average of $336). 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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See prices for flight routes from nearby airports that may be better suited for you.
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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 April 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$229FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$214Average$555FlexibilityNo cancel feeOn-time62%
DeltaCheapest$274Average$519FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$301Average$615FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$302Average$696FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$401Average$796FlexibilityNo cancel feeOn-time63%

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