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$186+ 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 4/22. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 17, 2025.

Round-trip from

$298
(Frontier)

One-way from

$186
(American Airlines)

Popular in

April

Cheapest in

September

Average price

$629
From Portland to Caribbean
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One-way flight from Portland to Caribbean
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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 17, 2025.

This Booking.com deal was found by Cheapflights users on 4/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/89:29 pmPWM - SJU
1 stop29h 22mFrontier
Sun 5/114:39 pmSJU - PWM
1 stop28h 01mFrontier
Deal found 4/16$308
This JetBlue deal was found by Cheapflights users on 4/16. 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 4/303:20 pmPWM - SJU
1 stop6h 07mJetBlue
Thu 5/87:01 amSJU - PWM
1 stop7h 39mJetBlue
Deal found 4/16$347
This Delta deal was found by Cheapflights users on 4/16. 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 4/275:32 amPWM - NAS
1 stop6h 04mDelta
Thu 5/155:50 pmNAS - PWM
1 stop6h 24mDelta
Deal found 4/16$373
This Southwest deal was found by Cheapflights users on 4/15. 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.
Fri 5/164:40 pmPWM - SJU
1 stop6h 50mSouthwest
Tue 5/205:20 amSJU - PWM
2 stops10h 00mSouthwest
Deal found 4/15$379
This Delta deal was found by Cheapflights users on 4/15. 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 11/12:35 pmPWM - SJU
1 stop8h 44mDelta
Mon 11/173:28 pmSJU - PWM
1 stop7h 31mDelta
Deal found 4/15$385
This Delta deal was found by Cheapflights users on 4/15. 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 4/285:32 amPWM - AUA
1 stop7h 08mDelta
Fri 5/21:55 pmAUA - PWM
1 stop10h 47mDelta
Deal found 4/15$401
This Delta deal was found by Cheapflights users on 4/17. 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 - MBJ
1 stop11h 00mDelta
Sun 5/111:15 pmMBJ - PWM
1 stop9h 59mDelta
Deal found 4/17$407
This American Airlines deal was found by Cheapflights users on 4/17. 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 5/94:01 pmPWM - MBJ
2 stops18h 09mAmerican Airlines
Sun 5/113:40 pmMBJ - PWM
2 stops17h 40mAmerican Airlines
Deal found 4/17$416
This JetBlue deal was found by Cheapflights users on 4/16. 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 5/163:35 pmPWM - SDQ
1 stop9h 17mJetBlue
Sat 5/173:09 amSDQ - PWM
1 stop11h 31mJetBlue
Deal found 4/16$421
This United Airlines deal was found by Cheapflights users on 4/16. 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 4/3012:45 pmPWM - SJU
2 stops11h 09mUnited Airlines
Thu 5/84:55 pmSJU - PWM
1 stop6h 32mUnited Airlines
Deal found 4/16$421
This American Airlines deal was found by Cheapflights users on 4/17. 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 10/175:11 pmPWM - NAS
2 stops18h 09mAmerican Airlines
Sat 10/2512:56 pmNAS - PWM
1 stop11h 37mAmerican Airlines
Deal found 4/17$430
This American Airlines deal was found by Cheapflights users on 4/17. 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 5/25:18 pmPWM - AUA
2 stops18h 02mAmerican Airlines
Wed 5/1412:29 pmAUA - PWM
2 stops11h 26mAmerican Airlines
Deal found 4/17$434

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 17, 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

Thu 5/8

9:29 pm-2:51 am

1 stop29h 22m

San Juan Luis Munoz Marin Intl

Sun 5/11

4:39 pm-8:40 pm

1 stop28h 01m

$308

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 4/30

3:20 pm-9:27 pm

1 stop6h 07m

San Juan Luis Munoz Marin Intl

Thu 5/8

7:01 am-2:40 pm

1 stop7h 39m

$347

PortlandNassau

PWM - NAS

PWMNAS

Portland

Sun 4/27

5:32 am-11:36 am

1 stop6h 04m

Nassau Intl

Thu 5/15

5:50 pm-12:14 am

1 stop6h 24m

$373

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Fri 5/16

4:40 pm-11:30 pm

1 stop6h 50m

San Juan Luis Munoz Marin Intl

Tue 5/20

5:20 am-3:20 pm

2 stops10h 00m

$379

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

Mon 4/28

5:32 am-12:40 pm

1 stop7h 08m

Oranjestad Reina Beatrix

Fri 5/2

1:55 pm-12:42 am

1 stop10h 47m

$401

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Fri 5/9

5:30 am-3:30 pm

1 stop11h 00m

Montego Bay Sangster Intl

Sun 5/11

1:15 pm-12:14 am

1 stop9h 59m

$407

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 5/26

5:30 am-4:31 pm

1 stop11h 01m

San Juan Luis Munoz Marin Intl

Fri 5/30

1:12 pm-12:14 am

1 stop11h 02m

$408

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Fri 5/9

4:01 pm-9:10 am

2 stops18h 09m

Montego Bay Sangster Intl

Sun 5/11

3:40 pm-10:20 am

2 stops17h 40m

$416

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 4/30

12:45 pm-11:54 pm

2 stops11h 09m

San Juan Luis Munoz Marin Intl

Thu 5/8

4:55 pm-11:27 pm

1 stop6h 32m

$421

PortlandSanto Domingo

PWM - SDQ

PWMSDQ

Portland

Fri 5/16

3:35 pm-12:52 am

1 stop9h 17m

Santo Domingo Las Americas

Sat 5/17

3:09 am-2:40 pm

1 stop11h 31m

$421

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/15

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 17, 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 17, 2025.
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,917 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,667 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
JetBlue
7.3
Good
2,926 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $186 on American Airlines. Other airlines that offer cheap prices include Delta from $237 and United Airlines from $264 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 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$229FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$214Average$550FlexibilityNo cancel feeOn-time62%
DeltaCheapest$274Average$518FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$301Average$615FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$305Average$698FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$401Average$796FlexibilityNo cancel feeOn-time63%

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