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$119+ 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 8/9. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$275
(Delta)

One-way from

$119
(Frontier)

Popular in

December

Cheapest in

August

Average price

$413
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. 7% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($21 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

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 July 29, 2025.

This Delta deal was found by Cheapflights users on 7/27. 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 9/266:33 amPWM - SJU
1 stop9h 47mDelta
Mon 9/296:00 pmSJU - PWM
1 stop6h 34mDelta
Deal found 7/27$275
This Priceline deal was found by Cheapflights users on 7/27. 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.
Tue 10/72:17 pmPWM - SJU
1 stop7h 07mJetBlue
Tue 10/146:00 amSJU - PWM
1 stop7h 22mJetBlue
Deal found 7/27$282
This United Airlines deal was found by Cheapflights users on 7/27. 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 9/266:00 amPWM - SJU
1 stop7h 45mUnited Airlines
Sun 9/281:05 amSJU - PWM
1 stop8h 06mUnited Airlines
Deal found 7/27$305
This Southwest deal was found by Cheapflights users on 7/27. 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 9/262:00 pmPWM - SJU
2 stops9h 50mSouthwest
Mon 9/295:50 amSJU - PWM
1 stop8h 55mSouthwest
Deal found 7/27$368
This JetBlue deal was found by Cheapflights users on 7/28. 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 10/157:30 amPWM - AUA
1 stop7h 40mJetBlue
Wed 10/221:20 pmAUA - PWM
1 stop8h 41mJetBlue
Deal found 7/28$375
This American Airlines deal was found by Cheapflights users on 7/27. 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.
Tue 10/712:34 pmPWM - SJU
2 stops9h 36mAmerican Airlines
Tue 10/145:30 amSJU - PWM
1 stop17h 18mAmerican Airlines
Deal found 7/27$385
This American Airlines deal was found by Cheapflights users on 7/26. 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 10/245:21 pmPWM - MBJ
2 stops16h 52mAmerican Airlines
Fri 10/313:20 pmMBJ - PWM
2 stops19h 48mAmerican Airlines
Deal found 7/26$420
This JetBlue deal was found by Cheapflights users on 7/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/127:30 amPWM - PUJ
1 stop8h 07mJetBlue
Fri 9/191:31 pmPUJ - PWM
1 stop8h 36mJetBlue
Deal found 7/29$424
This American Airlines deal was found by Cheapflights users on 7/27. 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 10/235:59 pmPWM - AUA
1 stop18h 31mAmerican Airlines
Thu 10/302:35 pmAUA - PWM
1 stop8h 13mAmerican Airlines
Deal found 7/27$427
This Delta deal was found by Cheapflights users on 7/28. 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 11/95:40 amPWM - MBJ
1 stop10h 53mDelta
Fri 11/142:06 pmMBJ - PWM
1 stop7h 53mDelta
Deal found 7/28$439
This Delta deal was found by Cheapflights users on 7/29. 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.
Fri 9/126:00 amPWM - GCM
1 stop6h 36mDelta
Fri 9/1912:52 pmGCM - PWM
1 stop10h 19mDelta
Deal found 7/29$455
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Wed 10/154:14 pmPWM - STT
2 stops18h 36mAmerican Airlines
Wed 10/225:20 pmSTT - PWM
2 stops18h 34mAmerican Airlines
Deal found 7/29$459

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 July 29, 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

Fri 9/26

6:33 am-4:20 pm

1 stop9h 47m

San Juan Luis Munoz Marin Intl

Mon 9/29

6:00 pm-12:34 am

1 stop6h 34m

$275

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 10/7

2:17 pm-9:24 pm

1 stop7h 07m

San Juan Luis Munoz Marin Intl

Tue 10/14

6:00 am-1:22 pm

1 stop7h 22m

$282

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Fri 9/26

6:00 am-1:45 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Sun 9/28

1:05 am-9:11 am

1 stop8h 06m

$305

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Fri 9/26

2:00 pm-11:50 pm

2 stops9h 50m

San Juan Luis Munoz Marin Intl

Mon 9/29

5:50 am-2:45 pm

1 stop8h 55m

$368

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

Wed 10/15

7:30 am-3:10 pm

1 stop7h 40m

Oranjestad Reina Beatrix

Wed 10/22

1:20 pm-10:01 pm

1 stop8h 41m

$375

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 10/7

12:34 pm-10:10 pm

2 stops9h 36m

San Juan Luis Munoz Marin Intl

Tue 10/14

5:30 am-10:48 pm

1 stop17h 18m

$385

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Fri 10/24

5:21 pm-9:13 am

2 stops16h 52m

Montego Bay Sangster Intl

Fri 10/31

3:20 pm-12:08 pm

2 stops19h 48m

$420

PortlandPunta Cana

PWM - PUJ

PWMPUJ

Portland

Fri 9/12

7:30 am-3:37 pm

1 stop8h 07m

Punta Cana

Fri 9/19

1:31 pm-10:07 pm

1 stop8h 36m

$424

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

Thu 10/23

5:59 pm-12:30 pm

1 stop18h 31m

Oranjestad Reina Beatrix

Thu 10/30

2:35 pm-10:48 pm

1 stop8h 13m

$427

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Sun 11/9

5:40 am-12:41 pm

1 stop7h 01m

Montego Bay Sangster Intl

Fri 11/14

2:07 pm-11:31 pm

1 stop9h 24m

$439

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 53 results
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6

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 July 29, 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.

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 July 29, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Copa Airlines from Portland to Caribbean. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,979 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Copa Airlines
7.5
Good
1,493 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,896 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 $119 on Frontier. Other airlines that offer cheap prices include JetBlue from $163 and Delta from $173 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 - Saint Thomas Island Cyril E King and Portland - Montego Bay Sangster 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 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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$229FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$214Average$543FlexibilityNo cancel feeOn-time62%
DeltaCheapest$274Average$499FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$285Average$698FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$322Average$656FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$401Average$751FlexibilityNo cancel feeOn-time63%

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