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Caribbean

$96+ 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 3/14. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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Cheap 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 January 27, 2026.

This United Airlines deal was found by Cheapflights users on 1/26. 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 2/23:12 pm
PWM
-
SJU
1 stop8h 24m
United Airlines
Fri 2/62:05 am
SJU
-
PWM
1 stop7h 56m
United Airlines
Deal found 1/26$212
This JetBlue deal was found by Cheapflights users on 1/25. 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 4/292:18 pm
PWM
-
SJU
1 stop9h 49m
JetBlue
Sat 5/96:25 am
SJU
-
PWM
1 stop6h 58m
JetBlue
Deal found 1/25$218
This United Airlines deal was found by Cheapflights users on 1/26. 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 2/23:12 pm
PWM
-
SJU
1 stop8h 24m
United Airlines
Wed 2/42:05 am
SJU
-
PWM
1 stop7h 56m
United Airlines
Deal found 1/26$227
This Trip.com deal was found by Cheapflights users on 1/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
PWM
-
SJU
1 stop6h 49m
JetBlue
Tue 6/23:00 pm
SJU
-
PWM
1 stop8h 36m
JetBlue
Deal found 1/25$231
This JetBlue deal was found by Cheapflights users on 1/26. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:00 am
PWM
-
SJU
1 stop8h 50m
JetBlue
Wed 4/154:10 pm
SJU
-
PWM
1 stop7h 49m
JetBlue
Deal found 1/26$233
This Trip.com deal was found by Cheapflights users on 1/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/302:18 pm
PWM
-
SJU
1 stop8h 32m
JetBlue
Sat 6/63:30 am
SJU
-
PWM
1 stop9h 53m
JetBlue
Deal found 1/25$237
This United Airlines deal was found by Cheapflights users on 1/26. 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.
Sat 2/72:31 pm
PWM
-
SJU
1 stop6h 51m
United Airlines
Tue 2/102:05 am
SJU
-
PWM
1 stop7h 56m
United Airlines
Deal found 1/26$256
This Delta deal was found by Cheapflights users on 1/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/25:30 am
PWM
-
SJU
1 stop8h 01m
Delta
Fri 2/66:05 pm
SJU
-
PWM
1 stop7h 15m
Delta
Deal found 1/26$276
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Wed 3/186:29 pm
PWM
-
AUA
2 stops21h 14m
American Airlines
Tue 3/2412:35 pm
AUA
-
PWM
2 stops21h 53m
American Airlines
Deal found 1/27$314
This American Airlines deal was found by Cheapflights users on 1/25. 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 4/256:00 am
PWM
-
AUA
1 stop10h 05m
American Airlines
Sat 5/212:55 pm
AUA
-
PWM
1 stop20h 59m
American Airlines
Deal found 1/25$315
This American Airlines deal was found by Cheapflights users on 1/25. 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 2/245:40 pm
PWM
-
SXM
2 stops21h 48m
American Airlines
Tue 3/31:29 pm
SXM
-
PWM
2 stops23h 30m
American Airlines
Deal found 1/25$316
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Sat 3/75:57 pm
PWM
-
PLS
1 stop18h 24m
American Airlines
Wed 3/1112:59 pm
PLS
-
PWM
1 stop10h 00m
American Airlines
Deal found 1/27$321

Find flight deals from Portland to Caribbean

Keep the following information in mind while searching for Portland to Caribbean flight deals. Data was last updated January 27, 2026.

Round-trip from

$212
(United Airlines)

One-way from

$96
(United Airlines)

Popular in

February

Cheapest in

November

Average price

$367
From Portland to Caribbean
Search Deals
One-way flight from Portland to Caribbean
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($52 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 27, 2026.
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

Sat 2/7

6:00 am-9:26 pm

2 stops14h 26m

San Juan Luis Munoz Marin Intl

Tue 2/10

2:05 am-9:01 am

1 stop7h 56m

$212

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 2/2

6:00 am-9:00 pm

2 stops14h 00m

San Juan Luis Munoz Marin Intl

Fri 2/6

2:05 am-2:39 pm

2 stops13h 34m

$225

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 2/2

3:12 pm-12:36 am

1 stop8h 24m

San Juan Luis Munoz Marin Intl

Wed 2/4

2:05 am-9:01 am

1 stop7h 56m

$227

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 2/2

5:30 am-2:31 pm

1 stop8h 01m

San Juan Luis Munoz Marin Intl

Wed 2/4

7:00 am-1:45 pm

1 stop7h 45m

$276

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 2/23

3:55 pm-12:05 am

1 stop7h 10m

San Juan Luis Munoz Marin Intl

Fri 2/27

6:30 am-1:45 pm

1 stop8h 15m

$276

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 2/2

5:30 am-2:31 pm

1 stop8h 01m

San Juan Luis Munoz Marin Intl

Fri 2/6

6:05 pm-12:20 am

1 stop7h 15m

$276

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 1/31

2:35 pm-11:57 pm

1 stop8h 22m

San Juan Luis Munoz Marin Intl

Tue 2/3

3:55 pm-10:27 pm

1 stop7h 32m

$302

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

Wed 3/4

5:40 pm-2:39 pm

2 stops19h 59m

Oranjestad Reina Beatrix

Wed 3/11

3:50 pm-12:14 pm

2 stops20h 24m

$314

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

Mon 3/16

6:00 pm-1:39 pm

2 stops19h 39m

Oranjestad Reina Beatrix

Mon 3/23

4:55 pm-12:14 pm

2 stops19h 19m

$314

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

Wed 3/18

6:29 pm-4:10 pm

2 stops21h 41m

Oranjestad Reina Beatrix

Tue 3/24

1:46 pm-10:59 pm

1 stop9h 13m

$314

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 60 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, January is the cheapest month in which you can book a flight from Portland, Maine to Caribbean (average of $88). Flying from Portland, Maine to Caribbean in November is currently the most expensive (average of $177). 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.

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 January 27, 2026.
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
4,268 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,268 reviews
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,119 reviews
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,205 reviews
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,197 reviews
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
JetBlue
7.2
Good
2,890 reviews
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 7h 10m. 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 $86 on Frontier. Other airlines that offer cheap prices include American Airlines from $146 and Southwest from $150 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 - George Town Owen Roberts 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, January is the cheapest month in which you can book a flight from Portland, Maine to Caribbean (average of $88). Flying from Portland, Maine to Caribbean in November is currently the most expensive (average of $177). 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 5 airlines flying from Portland to Caribbean

Discover the top 5 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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$176Average$483FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$190Average$610FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$241Average$618FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$256Average$593FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$648FlexibilityNo cancel feeOn-time63%

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