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$145+ 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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
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 October 28, 2025.

Round-trip from

$235
(American Airlines)

One-way from

$145
(American Airlines)

Popular in

February

Cheapest in

September

Average price

$364
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. 6% potential increase in price ($34 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 October 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 October 28, 2025.

This United Airlines deal was found by Cheapflights users on 10/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/106:00 amPWM - SJU
2 stops14h 00mUnited Airlines
Fri 11/148:30 amSJU - PWM
1 stop6h 49mUnited Airlines
Deal found 10/26$281
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/95:43 amPWM - NAS
1 stop5h 25mAmerican Airlines
Fri 11/1412:13 pmNAS - PWM
1 stop11h 46mAmerican Airlines
Deal found 10/28$289
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/66:37 pmPWM - NAS
2 stops16h 31mAmerican Airlines
Sat 11/1512:13 pmNAS - PWM
2 stops10h 19mAmerican Airlines
Deal found 10/28$293
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/55:17 pmPWM - PUJ
2 stops20h 39mAmerican Airlines
Wed 12/103:02 pmPUJ - PWM
1 stop7h 35mAmerican Airlines
Deal found 10/28$306
This American Airlines deal was found by Cheapflights users on 10/26. 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.
Thu 12/116:40 pmPWM - STT
2 stops19h 46mAmerican Airlines
Tue 12/166:17 pmSTT - PWM
2 stops18h 20mAmerican Airlines
Deal found 10/26$315
This American Airlines deal was found by Cheapflights users on 10/26. 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.
Thu 12/115:17 pmPWM - GCM
2 stops20h 49mAmerican Airlines
Tue 12/161:25 pmGCM - PWM
2 stops10h 12mAmerican Airlines
Deal found 10/26$315
This American Airlines deal was found by Cheapflights users on 10/26. 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.
Thu 11/277:02 amPWM - AUA
1 stop28h 37mAmerican Airlines
Thu 12/42:56 pmAUA - PWM
1 stop8h 56mAmerican Airlines
Deal found 10/26$315
This Delta deal was found by Cheapflights users on 10/28. 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.
Sat 11/156:35 amPWM - SXM
1 stop6h 30mDelta
Thu 11/204:20 pmSXM - PWM
2 stops24h 47mDelta
Deal found 10/28$316
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/157:02 amPWM - SXM
1 stop29h 58mAmerican Airlines
Thu 11/202:51 pmSXM - PWM
1 stop8h 42mAmerican Airlines
Deal found 10/28$319
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/165:17 pmPWM - AUA
2 stops20h 31mAmerican Airlines
Tue 12/235:55 pmAUA - PWM
2 stops20h 27mAmerican Airlines
Deal found 10/28$320
This Delta deal was found by Cheapflights users on 10/27. 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.
Thu 11/66:00 amPWM - GCM
1 stop6h 44mDelta
Mon 11/101:50 pmGCM - PWM
1 stop8h 29mDelta
Deal found 10/27$328
This United Airlines deal was found by Cheapflights users on 10/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/106:00 amPWM - NAS
1 stop5h 53mUnited Airlines
Wed 12/172:55 pmNAS - PWM
1 stop8h 14mUnited Airlines
Deal found 10/26$329

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 October 28, 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

Mon 1/12

5:20 am-5:03 pm

2 stops10h 43m

San Juan Luis Munoz Marin Intl

Fri 1/16

3:49 pm-10:07 pm

1 stop7h 18m

$235

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 11/10

6:00 am-9:00 pm

2 stops14h 00m

San Juan Luis Munoz Marin Intl

Fri 11/14

8:30 am-2:19 pm

1 stop6h 49m

$281

PortlandNassau

PWM - NAS

PWMNAS

Portland

Sun 11/9

7:02 am-1:59 pm

1 stop6h 57m

Nassau Intl

Fri 11/14

12:00 pm-10:54 pm

1 stop10h 54m

$289

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 3/4

3:05 pm-12:36 am

1 stop8h 31m

San Juan Luis Munoz Marin Intl

Tue 3/10

7:35 am-11:11 pm

2 stops15h 36m

$303

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 4/22

2:20 pm-10:47 pm

1 stop8h 27m

San Juan Luis Munoz Marin Intl

Sat 5/2

3:30 am-1:23 pm

1 stop9h 53m

$308

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Sun 1/11

6:00 am-1:49 pm

1 stop6h 49m

Saint Thomas Island Cyril E King

Tue 1/20

3:10 pm-10:29 pm

1 stop8h 19m

$315

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Tue 1/13

6:17 am-1:49 pm

1 stop6h 32m

Saint Thomas Island Cyril E King

Thu 1/22

1:52 pm-10:29 pm

1 stop9h 37m

$315

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Mon 1/12

5:20 am-3:56 pm

2 stops9h 36m

Saint Thomas Island Cyril E King

Tue 1/20

1:50 pm-12:05 pm

2 stops23h 15m

$315

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Sun 1/11

6:00 am-1:49 pm

1 stop6h 49m

Saint Thomas Island Cyril E King

Wed 1/21

5:20 pm-12:20 am

1 stop8h 00m

$315

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Wed 11/26

3:52 pm-5:27 pm

2 stops24h 35m

Saint Thomas Island Cyril E King

Wed 12/3

6:17 pm-11:37 am

2 stops18h 20m

$315

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 60 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, January is the cheapest month in which you can book a flight from Portland, Maine to Caribbean (average of $85). Flying from Portland, Maine to Caribbean in September is currently the most expensive (average of $147). 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 October 28, 2025.

It’s optimal to fly from Portland, Maine to Caribbean in the evening. By choosing this option you can save up to 48% on the cost of your flight, compared to a flight in the morning.

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 October 28, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United 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
4,240 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,994 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,001 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,032 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,908 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Portland, Maine to Caribbean?

    Departing from Portland, Maine to Caribbean will take you 8h 27m. There are 1758 mi between Portland, Maine and Caribbean. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $145 on American Airlines. Other airlines that offer cheap prices include Delta from $152 and United Airlines from $156 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 - Punta Cana, Portland - San Juan Luis Munoz Marin Intl and Portland - Saint Thomas Island Cyril E King.

  • 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, January is the cheapest month in which you can book a flight from Portland, Maine to Caribbean (average of $85). Flying from Portland, Maine to Caribbean in September is currently the most expensive (average of $147). 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

Browse thousands of different options on Cheapflights for your next trip

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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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$228FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$249Average$698FlexibilityNo cancel feeOn-time69%
DeltaCheapest$275Average$511FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$301Average$633FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$361Average$601FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$371Average$753FlexibilityNo cancel feeOn-time63%

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