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Caribbean Islands

$138+ 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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Round-trip from

$251
(United Airlines)

One-way from

$138
(Delta)

Popular in

April

Cheapest in

September

Average price

$385
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. 9% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This United Airlines deal was found by Cheapflights users on 4/30. 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.
Fri 5/306:10 amPWM - SJU
1 stop7h 35mUnited Airlines
Fri 6/64:55 pmSJU - PWM
1 stop7h 02mUnited Airlines
Deal found 4/30$251
This Delta deal was found by Cheapflights users on 5/1. 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.
Sat 5/242:30 pmPWM - SJU
1 stop9h 12mDelta
Wed 6/41:12 pmSJU - PWM
1 stop11h 02mDelta
Deal found 5/1$275
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/107:30 pmPWM - SJU
1 stop13h 06mFrontier
Thu 5/156:00 amSJU - PWM
1 stop14h 29mFrontier
Deal found 4/30$308
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/244:01 pmPWM - SJU
1 stop7h 58mAmerican Airlines
Wed 6/47:15 amSJU - PWM
2 stops13h 32mAmerican Airlines
Deal found 4/30$383
This JetBlue deal was found by Cheapflights users on 4/30. 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.
Mon 6/162:19 pmPWM - SJU
1 stop10h 35mJetBlue
Thu 6/192:36 pmSJU - PWM
1 stop9h 16mJetBlue
Deal found 4/30$394
This American Airlines deal was found by Cheapflights users on 5/1. 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.
Fri 5/95:24 pmPWM - MBJ
2 stops17h 29mAmerican Airlines
Sun 5/112:41 pmMBJ - PWM
2 stops20h 07mAmerican Airlines
Deal found 5/1$416
This Delta deal was found by Cheapflights users on 4/30. 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.
Fri 5/165:30 amPWM - AUA
1 stop8h 40mDelta
Sat 5/243:25 pmAUA - PWM
1 stop8h 34mDelta
Deal found 4/30$429
This American Airlines deal was found by Cheapflights users on 5/1. 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.
Sat 11/12:53 pmPWM - NAS
1 stop21h 22mAmerican Airlines
Sat 11/85:00 pmNAS - PWM
1 stop5h 30mAmerican Airlines
Deal found 5/1$430
This Delta deal was found by Cheapflights users on 4/30. 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.
Thu 11/136:00 amPWM - NAS
1 stop7h 11mDelta
Mon 11/171:25 pmNAS - PWM
1 stop10h 06mDelta
Deal found 4/30$431
This American Airlines deal was found by Cheapflights users on 5/1. 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.
Fri 9/126:46 pmPWM - AUA
2 stops18h 34mAmerican Airlines
Mon 9/224:45 pmAUA - PWM
2 stops20h 28mAmerican Airlines
Deal found 5/1$434
This Delta deal was found by Cheapflights users on 4/30. 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.
Fri 5/162:30 pmPWM - SDQ
1 stop9h 49mDelta
Mon 5/192:28 pmSDQ - PWM
1 stop9h 46mDelta
Deal found 4/30$451
This JetBlue deal was found by Cheapflights users on 4/30. 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.
Fri 9/197:30 amPWM - PUJ
1 stop9h 44mJetBlue
Tue 9/2311:30 amPUJ - PWM
1 stop10h 29mJetBlue
Deal found 4/30$458

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 May 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

Fri 5/30

6:10 am-1:45 pm

1 stop7h 35m

San Juan Luis Munoz Marin Intl

Fri 6/6

4:55 pm-11:57 pm

1 stop7h 02m

$251

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 5/24

2:30 pm-11:42 pm

1 stop9h 12m

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

Thu 5/15

9:29 pm-8:58 am

1 stop11h 29m

San Juan Luis Munoz Marin Intl

Mon 5/19

6:00 am-8:40 pm

1 stop14h 40m

$308

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 5/24

4:01 pm-11:59 pm

1 stop7h 58m

San Juan Luis Munoz Marin Intl

Wed 6/4

7:15 am-8:47 pm

2 stops13h 32m

$383

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 6/16

2:19 pm-12:54 am

1 stop10h 35m

San Juan Luis Munoz Marin Intl

Thu 6/19

2:36 pm-11:52 pm

1 stop9h 16m

$394

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Fri 5/30

7:35 am-1:35 pm

1 stop7h 00m

Montego Bay Sangster Intl

Wed 6/11

2:40 pm-11:03 pm

1 stop7h 23m

$424

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

Fri 5/16

5:30 am-2:10 pm

1 stop8h 40m

Oranjestad Reina Beatrix

Sat 5/24

3:25 pm-11:59 pm

1 stop8h 34m

$429

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

Fri 9/12

6:46 pm-1:20 pm

2 stops18h 34m

Oranjestad Reina Beatrix

Mon 9/22

4:45 pm-1:13 pm

2 stops20h 28m

$434

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

$451

PortlandPunta Cana

PWM - PUJ

PWMPUJ

Portland

Fri 9/19

7:30 am-5:14 pm

1 stop9h 44m

Punta Cana

Tue 9/23

11:30 am-9:59 pm

1 stop10h 29m

$458

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 38 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 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 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 May 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.

Rainfall in Caribbean Islands by month

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

In terms of precipitation, rainfall in Caribbean Islands 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 Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

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

If weather is an important factor for your trip to Caribbean Islands, 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 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 May 1, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and LATAM Airlines from Portland to Caribbean Islands to help guide your decision. 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
4,293 reviews

Crew

8.6

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

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
4,293 reviews
Southwest
8.0
Very good
4,293 reviews

Crew

8.6

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

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
7,934 reviews
Southwest
8.0
Very good
4,293 reviews

Crew

8.6

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

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
4,293 reviews

Crew

8.6

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

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!
Copa Airlines
7.5
Good
1,415 reviews
Southwest
8.0
Very good
4,293 reviews

Crew

8.6

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

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
8,696 reviews
Southwest
8.0
Very good
4,293 reviews

Crew

8.6

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

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 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?

    $138 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on American Airlines and United Airlines, with prices starting from $151 and $223, 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 - Oranjestad Reina Beatrix and Portland - Montego Bay Sangster Intl.

  • 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 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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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$229FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$214Average$555FlexibilityNo cancel feeOn-time62%
DeltaCheapest$274Average$517FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$301Average$616FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$302Average$720FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$401Average$797FlexibilityNo cancel feeOn-time63%

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