Caribbean

$112+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
May 28 — Jun 41
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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 April 28, 2026.

This United Airlines deal was found by Cheapflights users on 4/24. 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.
Sun 5/106:00 am
PWM
-
STT
1 stop7h 08m
United Airlines
Wed 5/132:10 pm
STT
-
PWM
1 stop9h 19m
United Airlines
Deal found 4/24$250
This American Airlines deal was found by Cheapflights users on 4/26. 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.
Sun 5/36:00 am
PWM
-
STT
2 stops10h 15m
American Airlines
Sun 5/1011:27 am
STT
-
PWM
1 stop11h 59m
American Airlines
Deal found 4/26$275
This Delta deal was found by Cheapflights users on 4/23. 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.
Wed 9/161:35 pm
PWM
-
SJU
1 stop8h 25m
Delta
Wed 9/237:00 am
SJU
-
PWM
1 stop6h 54m
Delta
Deal found 4/23$276
This American Airlines deal was found by Cheapflights users on 4/24. 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
-
STT
2 stops19h 47m
American Airlines
Wed 12/162:49 pm
STT
-
PWM
2 stops9h 48m
American Airlines
Deal found 4/24$289
This American Airlines deal was found by Cheapflights users on 4/27. 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 10/201:05 pm
PWM
-
SJU
2 stops10h 45m
American Airlines
Mon 10/265:25 am
SJU
-
PWM
1 stop13h 51m
American Airlines
Deal found 4/27$302
This American Airlines deal was found by Cheapflights users on 4/23. 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 8/186:00 am
PWM
-
SJU
2 stops17h 59m
American Airlines
Fri 8/216:51 am
SJU
-
PWM
1 stop13h 26m
American Airlines
Deal found 4/23$304
This American Airlines deal was found by Cheapflights users on 4/27. 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 5/2710:57 am
PWM
-
SJU
1 stop12h 04m
American Airlines
Wed 6/310:29 am
SJU
-
PWM
2 stops13h 22m
American Airlines
Deal found 4/27$307
This American Airlines deal was found by Cheapflights users on 4/23. 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 8/195:13 pm
PWM
-
SJU
2 stops21h 25m
American Airlines
Sat 8/223:44 pm
SJU
-
PWM
2 stops24h 49m
American Airlines
Deal found 4/23$309
This Delta deal was found by Cheapflights users on 4/24. 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.
Wed 5/276:00 am
PWM
-
GCM
1 stop6h 54m
Delta
Tue 6/21:19 pm
GCM
-
PWM
1 stop8h 50m
Delta
Deal found 4/24$321
This United Airlines deal was found by Cheapflights users on 4/24. 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 5/1311:08 am
PWM
-
SJU
2 stops10h 16m
United Airlines
Tue 5/191:00 am
SJU
-
PWM
1 stop7h 49m
United Airlines
Deal found 4/24$323
This United Airlines deal was found by Cheapflights users on 4/23. 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 9/165:15 am
PWM
-
SJU
1 stop7h 39m
United Airlines
Tue 9/221:00 am
SJU
-
PWM
2 stops9h 02m
United Airlines
Deal found 4/23$324
This Delta deal was found by Cheapflights users on 4/24. 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.
Tue 5/261:18 pm
PWM
-
GCM
2 stops23h 36m
Delta
Tue 6/21:19 pm
GCM
-
PWM
1 stop8h 50m
Delta
Deal found 4/24$326

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 April 28, 2026.

Round-trip from

$250
(United Airlines)

One-way from

$112
(Delta)

Popular in

April

Cheapest in

October

Average price

$711
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. 5% potential price decrease ($25 potential savings vs. average RT price).
Average for round-trip flights in April 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 April 28, 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
Quickest round-trip

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Sun 5/10

5:30 am-12:20 pm

1 stop6h 50m

Saint Thomas Island Cyril E King

Wed 5/13

4:45 pm-11:59 pm

1 stop7h 14m

$250

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Sun 5/10

7:23 pm-12:35 pm

1 stop17h 12m

Saint Thomas Island Cyril E King

Wed 5/13

12:25 pm-11:26 pm

2 stops11h 01m

$250

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 5/13

2:08 pm-9:24 pm

1 stop7h 16m

San Juan Luis Munoz Marin Intl

Tue 5/19

1:00 am-8:49 am

1 stop7h 49m

$302

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Wed 8/12

6:12 pm-11:30 am

2 stops18h 18m

George Town Owen Roberts Intl

Mon 8/24

2:10 pm-12:40 pm

2 stops21h 30m

$331

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Thu 5/28

6:00 am-11:01 pm

1 stop17h 01m

San Juan Luis Munoz Marin Intl

Mon 6/1

6:20 am-9:46 pm

1 stop15h 26m

$342

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

Mon 6/1

6:54 pm-12:59 pm

1 stop18h 05m

Oranjestad Reina Beatrix

Mon 6/8

5:59 pm-2:24 pm

2 stops20h 25m

$366

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

Fri 5/8

7:23 pm-11:40 am

1 stop16h 17m

Oranjestad Reina Beatrix

Fri 5/29

2:33 pm-9:53 am

2 stops19h 20m

$366

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Wed 6/3

6:00 am-12:40 pm

1 stop6h 40m

Simpson Bay Princess Juliana

Mon 6/8

4:43 pm-2:24 pm

2 stops21h 41m

$377

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 5/30

6:00 am-1:45 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Wed 6/3

1:00 am-9:11 am

1 stop8h 11m

$385

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Fri 7/24

6:00 pm-11:47 am

2 stops18h 47m

Montego Bay Sangster Intl

Tue 7/28

5:14 pm-2:16 pm

2 stops20h 02m

$399

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/26

Showing 1-10 of 60 resultsSorted by cheapest first
1
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

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

Booking 31 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.

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 December is currently the most expensive (average of $298). 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 April 28, 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

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 6h 54m. There are 1799 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 December is currently the most expensive (average of $298). 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 April 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$156Average$589FlexibilityNo cancel feeOn-time62%
DeltaCheapest$176Average$422FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$235Average$584FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$256Average$565FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$660FlexibilityNo cancel feeOn-time63%

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