Caribbean

$140+ 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 7/18. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Jul 8 — Jul 151
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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 June 8, 2026.

This Delta deal was found by Cheapflights users on 6/3. 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 9/192:35 pm
PWM
-
SJU
1 stop9h 09m
Delta
Sat 9/261:32 pm
SJU
-
PWM
1 stop10h 27m
Delta
Deal found 6/3$302
This American Airlines deal was found by Cheapflights users on 6/3. 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 9/165:42 pm
PWM
-
SJU
2 stops20h 12m
American Airlines
Wed 9/236:27 am
SJU
-
PWM
2 stops17h 32m
American Airlines
Deal found 6/3$307
This Delta deal was found by Cheapflights users on 6/3. 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 11/166:00 am
PWM
-
NAS
1 stop9h 30m
Delta
Sat 11/211:00 pm
NAS
-
PWM
1 stop10h 49m
Delta
Deal found 6/3$340
This American Airlines deal was found by Cheapflights users on 6/4. 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 10/206:00 am
PWM
-
SJU
2 stops12h 05m
American Airlines
Mon 10/265:25 am
SJU
-
PWM
1 stop13h 00m
American Airlines
Deal found 6/4$342
This American Airlines deal was found by Cheapflights users on 6/4. 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 12/36:38 pm
PWM
-
PUJ
1 stop17h 51m
American Airlines
Wed 12/95:30 pm
PUJ
-
PWM
2 stops19h 41m
American Airlines
Deal found 6/4$345
This American Airlines deal was found by Cheapflights users on 6/4. 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 12/96:38 pm
PWM
-
PUJ
1 stop17h 51m
American Airlines
Mon 12/145:30 pm
PUJ
-
PWM
2 stops19h 07m
American Airlines
Deal found 6/4$350
This Delta deal was found by Cheapflights users on 6/4. 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 11/166:00 am
PWM
-
NAS
1 stop7h 30m
Delta
Fri 11/201:20 pm
NAS
-
PWM
1 stop9h 03m
Delta
Deal found 6/4$350
This Delta deal was found by Cheapflights users on 6/4. 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 11/96:00 am
PWM
-
MBJ
1 stop10h 35m
Delta
Fri 11/131:50 pm
MBJ
-
PWM
1 stop9h 59m
Delta
Deal found 6/4$352
This American Airlines deal was found by Cheapflights users on 6/7. 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 10/201:05 pm
PWM
-
SJU
2 stops10h 45m
American Airlines
Wed 11/42:41 pm
SJU
-
PWM
2 stops9h 57m
American Airlines
Deal found 6/7$352
This American Airlines deal was found by Cheapflights users on 6/4. 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 12/95:17 pm
PWM
-
PUJ
2 stops20h 39m
American Airlines
Sun 12/135:30 pm
PUJ
-
PWM
2 stops19h 07m
American Airlines
Deal found 6/4$355
This American Airlines deal was found by Cheapflights users on 6/4. 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 12/15:37 pm
PWM
-
SXM
2 stops21h 48m
American Airlines
Tue 12/83:20 pm
SXM
-
PWM
2 stops21h 51m
American Airlines
Deal found 6/4$362
This American Airlines deal was found by Cheapflights users on 6/6. 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 11/143:53 pm
PWM
-
SJU
1 stop6h 54m
American Airlines
Sat 11/216:25 am
SJU
-
PWM
1 stop12h 48m
American Airlines
Deal found 6/6$362

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 June 8, 2026.

Round-trip from

$302
(Delta)

One-way from

$134
(Delta)

Popular in

April

Cheapest in

July

Average price

$474
From Portland to Caribbean
One-way flight from Portland to Caribbean
Highest demand for flights based on searches. 11% potential increase in price ($58 potential increase over avg. RT price).
Cheapest flight prices on average. 6% potential price decrease ($26 potential savings vs. average RT price).
Average for round-trip flights in June 2026

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 June 8, 2026.
Use the filters below to find and compare flights from Portland to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 10/6

2:35 pm-11:56 pm

1 stop9h 21m

San Juan Luis Munoz Marin Intl

Sun 10/11

7:00 am-1:53 pm

1 stop6h 53m

$302

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 9/19

6:05 am-4:31 pm

1 stop10h 26m

San Juan Luis Munoz Marin Intl

Sat 9/26

7:00 am-1:54 pm

1 stop6h 54m

$302

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 10/20

6:00 am-1:45 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Wed 11/4

7:45 am-10:57 pm

2 stops16h 12m

$312

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 10/20

2:35 pm-11:56 pm

1 stop9h 21m

San Juan Luis Munoz Marin Intl

Mon 10/26

7:00 am-1:53 pm

1 stop6h 53m

$312

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 9/16

2:35 pm-11:44 pm

1 stop9h 09m

San Juan Luis Munoz Marin Intl

Wed 9/23

7:00 am-1:54 pm

1 stop6h 54m

$312

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 10/20

2:35 pm-11:56 pm

1 stop9h 21m

San Juan Luis Munoz Marin Intl

Wed 11/4

7:00 am-1:53 pm

1 stop7h 53m

$312

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Fri 8/28

6:05 am-1:42 pm

1 stop7h 37m

San Juan Luis Munoz Marin Intl

Sun 8/30

5:50 pm-12:59 am

1 stop7h 09m

$312

PortlandNassau

PWM - NAS

PWMNAS

Portland

Mon 11/16

6:00 am-3:30 pm

1 stop9h 30m

Nassau Intl

Sat 11/21

1:00 pm-11:49 pm

1 stop10h 49m

$340
Quickest round-trip

PortlandNassau

PWM - NAS

PWMNAS

Portland

Thu 7/30

6:00 am-11:51 am

1 stop5h 51m

Nassau Intl

Sun 8/2

3:26 pm-11:14 pm

1 stop7h 48m

$340

PortlandNassau

PWM - NAS

PWMNAS

Portland

Mon 11/16

6:00 am-1:30 pm

1 stop7h 30m

Nassau Intl

Fri 11/20

2:55 pm-10:23 pm

1 stop7h 28m

$350

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/5

Showing 1-10 of 60 resultsSorted by cheapest first
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2
3
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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, February is the cheapest month in which you can book a flight from Portland, Maine to Caribbean (average of $101). Flying from Portland, Maine to Caribbean in August is currently the most expensive (average of $303). 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.

How far ahead should I book a flight from Portland, Maine to Caribbean?

Booking 33 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland, Maine to Caribbean. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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 June 8, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited 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.

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

7.9

Food

7.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

7.9

Food

7.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

7.9

Food

7.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

7.9

Food

7.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

7.9

Food

7.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

7.9

Food

7.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

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 9h 21m. 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 $106 on United Airlines. Other airlines that offer cheap prices include American Airlines from $108 and Southwest from $141 one-way.

  • What are the most popular routes from Portland, Maine to Caribbean?

  • 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, February is the cheapest month in which you can book a flight from Portland, Maine to Caribbean (average of $101). Flying from Portland, Maine to Caribbean in August is currently the most expensive (average of $303). 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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Alternative routes for Portland to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.

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 June 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$156Average$575FlexibilityNo cancel feeOn-time62%
DeltaCheapest$176Average$413FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$235Average$654FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$256Average$562FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$300Average$755FlexibilityNo cancel feeOn-time63%

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