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$121+ 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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
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 junio 12, 2025.

Round-trip from

$203
(Priceline)

One-way from

$121
(Delta)

Popular in

December

Cheapest in

September

Average price

$530
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. 5% potential increase in price ($26 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 June 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 junio 12, 2025.

This Priceline deal was found by Cheapflights users on 6/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/46:12 pmPWM - SJU
1 stop13h 47mFrontier
dom. 10/129:07 amSJU - PWM
1 stop25h 58mFrontier
Deal found 6/10$203
This Delta deal was found by Cheapflights users on 6/10. 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. 8/192:36 pmPWM - SJU
1 stop9h 15mDelta
sáb. 8/2312:50 pmSJU - PWM
1 stop11h 13mDelta
Deal found 6/10$275
This Delta deal was found by Cheapflights users on 6/9. 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. 10/215:40 amPWM - NAS
1 stop6h 18mDelta
mar. 10/281:25 pmNAS - PWM
1 stop10h 06mDelta
Deal found 6/9$349
This Delta deal was found by Cheapflights users on 6/11. 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. 9/96:00 amPWM - MBJ
1 stop6h 55mDelta
jue. 9/251:12 pmMBJ - PWM
1 stop9h 51mDelta
Deal found 6/11$371
This American Airlines deal was found by Cheapflights users on 6/11. 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. 9/96:00 amPWM - MBJ
2 stops8h 38mAmerican Airlines
jue. 9/254:09 pmMBJ - PWM
2 stops18h 38mAmerican Airlines
Deal found 6/11$375
This United Airlines deal was found by Cheapflights users on 6/12. 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. 7/43:50 pmPWM - SJU
1 stop8h 12mUnited Airlines
mié. 7/91:10 amSJU - PWM
2 stops13h 14mUnited Airlines
Deal found 6/12$381
This American Airlines deal was found by Cheapflights users on 6/12. 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.
jue. 10/165:54 amPWM - AUA
1 stop7h 01mAmerican Airlines
jue. 10/235:20 pmAUA - PWM
1 stop7h 13mAmerican Airlines
Deal found 6/12$386
This JetBlue deal was found by Cheapflights users on 6/10. 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.
mar. 7/152:19 pmPWM - SJU
1 stop9h 15mJetBlue
sáb. 7/196:00 pmSJU - PWM
1 stop6h 17mJetBlue
Deal found 6/10$387
This American Airlines deal was found by Cheapflights users on 6/9. 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. 10/215:54 amPWM - NAS
2 stops12h 46mAmerican Airlines
mié. 10/293:20 pmNAS - PWM
2 stops8h 20mAmerican Airlines
Deal found 6/9$395
This Southwest deal was found by Cheapflights users on 6/12. 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. 7/410:45 amPWM - SJU
1 stop10h 55mSouthwest
jue. 7/101:30 pmSJU - PWM
2 stops10h 35mSouthwest
Deal found 6/12$408
This Delta deal was found by Cheapflights users on 6/10. 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. 9/195:40 amPWM - PUJ
1 stop7h 37mDelta
mar. 9/232:29 pmPUJ - PWM
1 stop9h 02mDelta
Deal found 6/10$413
This American Airlines deal was found by Cheapflights users on 6/12. 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. 9/195:24 pmPWM - PUJ
2 stops18h 35mAmerican Airlines
mar. 9/234:25 pmPUJ - PWM
2 stops20h 04mAmerican Airlines
Deal found 6/12$417

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 junio 12, 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

sáb. 10/4

6:12 pm-7:59 am

1 stop13h 47m

San Juan Luis Munoz Marin Intl

dom. 10/12

9:07 am-11:05 am

1 stop25h 58m

$203

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

mar. 8/19

2:36 pm-11:51 pm

1 stop9h 15m

San Juan Luis Munoz Marin Intl

sáb. 8/23

12:50 pm-12:03 am

1 stop11h 13m

$275

PortlandNassau

PWM - NAS

PWMNAS

Portland

mar. 10/21

5:40 am-11:58 am

1 stop6h 18m

Nassau Intl

mar. 10/28

1:25 pm-11:31 pm

1 stop10h 06m

$349

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

mar. 9/9

6:00 am-11:55 am

1 stop6h 55m

Montego Bay Sangster Intl

jue. 9/25

1:12 pm-12:03 am

1 stop9h 51m

$371

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

mar. 9/9

6:00 am-1:38 pm

2 stops8h 38m

Montego Bay Sangster Intl

jue. 9/25

4:09 pm-11:47 am

2 stops18h 38m

$375

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

vie. 7/4

3:50 pm-12:02 am

1 stop8h 12m

San Juan Luis Munoz Marin Intl

mié. 7/9

1:10 am-2:24 pm

2 stops13h 14m

$381

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

jue. 10/16

5:54 am-12:55 pm

1 stop7h 01m

Oranjestad Reina Beatrix

jue. 10/23

5:20 pm-12:33 am

1 stop7h 13m

$386

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

mar. 7/15

2:19 pm-11:34 pm

1 stop9h 15m

San Juan Luis Munoz Marin Intl

sáb. 7/19

6:00 pm-12:17 am

1 stop6h 17m

$387

PortlandNassau

PWM - NAS

PWMNAS

Portland

mar. 10/21

5:54 am-6:40 pm

2 stops12h 46m

Nassau Intl

mié. 10/29

3:20 pm-11:40 pm

2 stops8h 20m

$395

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

vie. 7/4

10:45 am-9:40 pm

1 stop10h 55m

San Juan Luis Munoz Marin Intl

jue. 7/10

1:30 pm-12:05 am

2 stops10h 35m

$408

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 40 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 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 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 junio 12, 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 junio 12, 2025.
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.1

Crew

8.6

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.1

Crew

8.6

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
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.1

Crew

8.6

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
1,785 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.1

Crew

8.6

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
1,451 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.1

Crew

8.6

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
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.1

Crew

8.6

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. 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 $121 on Delta. Other airlines that offer cheap prices include Frontier from $124 and American Airlines from $202 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 - San Juan Luis Munoz Marin Intl, Portland - Punta Cana and Portland - Oranjestad Reina Beatrix.

  • 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 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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Alternative routes for Portland to Caribbean

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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$229FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$214Average$560FlexibilityNo cancel feeOn-time62%
DeltaCheapest$274Average$534FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$302Average$693FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$322Average$623FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$401Average$752FlexibilityNo cancel feeOn-time63%

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