HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$121+ Cheap flights from Portland, ME (PWM) to Caribbean Islands

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 5/11. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
apr. 8 — apr. 151
di 4/8
di 4/15
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Caribbean Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Portland to Caribbean Islands

Keep the following information in mind while searching for Portland to Caribbean Islands flight deals. Data was last updated april 3, 2025.

Round-trip from

$262
(United Airlines)

One-way from

$121
(American Airlines)

Popular in

April

Cheapest in

September

Average price

$645
From Portland to Caribbean Islands
Search Deals
One-way flight from Portland to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($56 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 April 2025
Search Deals

Find flight deals from Portland to Caribbean Islands

Cheapest flights from Portland to Caribbean Islands
Explore the most affordable flight options available from Portland to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on april 3, 2025.

This United Airlines deal was found by Cheapflights users on 4/2. 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.
vr 9/193:15 pmPWM - SJU
1 stop8h 42mUnited Airlines
vr 9/264:55 pmSJU - PWM
1 stop7h 01mUnited Airlines
Deal found 4/2$262
This American Airlines deal was found by Cheapflights users on 4/2. 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.
vr 9/196:46 pmPWM - SJU
2 stops17h 59mAmerican Airlines
vr 9/265:25 pmSJU - PWM
2 stops18h 29mAmerican Airlines
Deal found 4/2$266
This Booking.com deal was found by Cheapflights users on 4/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
za 4/1210:12 amPWM - SJU
1 stop15h 38mFrontier
do 4/179:35 pmSJU - PWM
1 stop19h 28mFrontier
Deal found 4/2$306
This JetBlue deal was found by Cheapflights users on 4/1. 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.
za 4/265:35 pmPWM - SJU
1 stop9h 15mJetBlue
wo 4/305:50 amSJU - PWM
1 stop8h 35mJetBlue
Deal found 4/1$313
This Southwest deal was found by Cheapflights users on 4/1. 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.
za 4/265:00 pmPWM - SJU
1 stop6h 35mSouthwest
do 5/16:05 amSJU - PWM
1 stop9h 50mSouthwest
Deal found 4/1$339
This American Airlines deal was found by Cheapflights users on 4/1. 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.
ma 4/286:00 amPWM - NAS
1 stop5h 37mAmerican Airlines
do 5/112:27 pmNAS - PWM
1 stop10h 22mAmerican Airlines
Deal found 4/1$373
This United Airlines deal was found by Cheapflights users on 4/2. 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.
wo 4/306:00 amPWM - NAS
1 stop8h 59mUnited Airlines
zo 5/45:00 pmNAS - PWM
2 stops18h 02mUnited Airlines
Deal found 4/2$377
This American Airlines deal was found by Cheapflights users on 4/3. 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.
ma 9/225:18 pmPWM - AUA
1 stop18h 07mAmerican Airlines
wo 10/15:25 pmAUA - PWM
1 stop17h 45mAmerican Airlines
Deal found 4/3$381
This Delta deal was found by Cheapflights users on 4/2. 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.
vr 5/25:20 amPWM - NAS
1 stop10h 40mDelta
di 5/65:25 pmNAS - PWM
1 stop6h 34mDelta
Deal found 4/2$383
This Delta deal was found by Cheapflights users on 4/2. 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.
vr 5/25:32 amPWM - AUA
1 stop7h 08mDelta
wo 5/141:55 pmAUA - PWM
1 stop10h 19mDelta
Deal found 4/2$401
This JetBlue Airways deal was found by Cheapflights users on 4/2. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vr 5/167:12 amPWM - SDQ
1 stop12h 42mJetBlue
zo 5/183:09 amSDQ - PWM
1 stop11h 31mJetBlue
Deal found 4/2$421
This American Airlines deal was found by Cheapflights users on 4/2. 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.
vr 5/95:24 pmPWM - MBJ
2 stops17h 29mAmerican Airlines
zo 5/1110:10 amMBJ - PWM
1 stop11h 56mAmerican Airlines
Deal found 4/2$433

Cheapflights Fare Finder

Customize your flight search to find flights from Portland to Caribbean Islands 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 3, 2025.
Use the filters below to find and compare flights from Portland to Caribbean Islands that are best for you.

Fly from

Portland

Fly to

Caribbean Islands

Route

Depart

Return

Price

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

vr 9/19

3:15 pm-11:57 pm

1 stop8h 42m

San Juan Luis Munoz Marin Intl

vr 9/26

4:55 pm-11:56 pm

1 stop7h 01m

$262

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

vr 9/19

6:46 pm-12:45 pm

2 stops17h 59m

San Juan Luis Munoz Marin Intl

vr 9/26

5:25 pm-11:54 am

2 stops18h 29m

$266

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

zo 4/13

10:08 am-8:33 am

1 stop22h 25m

San Juan Luis Munoz Marin Intl

do 4/17

9:35 pm-5:03 pm

1 stop19h 28m

$308

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

za 4/26

5:35 pm-2:50 am

1 stop9h 15m

San Juan Luis Munoz Marin Intl

wo 4/30

5:50 am-2:25 pm

1 stop8h 35m

$313

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

za 4/26

5:00 pm-11:35 pm

1 stop6h 35m

San Juan Luis Munoz Marin Intl

do 5/1

6:05 am-3:55 pm

1 stop9h 50m

$339

PortlandNassau

PWM - NAS

PWMNAS

Portland

ma 4/28

6:00 am-11:37 am

1 stop5h 37m

Nassau Intl

do 5/1

12:27 pm-10:49 pm

1 stop10h 22m

$373

PortlandNassau

PWM - NAS

PWMNAS

Portland

wo 4/30

6:00 am-2:59 pm

1 stop8h 59m

Nassau Intl

zo 5/4

5:00 pm-11:02 am

2 stops18h 02m

$377

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

ma 9/22

5:18 pm-11:25 am

1 stop18h 07m

Oranjestad Reina Beatrix

wo 10/1

5:25 pm-11:10 am

1 stop17h 45m

$381

PortlandNassau

PWM - NAS

PWMNAS

Portland

vr 5/2

5:20 am-4:00 pm

1 stop10h 40m

Nassau Intl

di 5/6

5:25 pm-11:59 pm

1 stop6h 34m

$383

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

vr 5/2

5:32 am-12:40 pm

1 stop7h 08m

Oranjestad Reina Beatrix

di 5/13

1:55 pm-12:14 am

1 stop10h 19m

$401

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 39 results
1
2
3
4

Best time to book a flight from Portland to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands

What is the cheapest month to book a flight from Portland, Maine to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Caribbean Islands (average of $254). Flying from Portland, Maine to Caribbean Islands in December is currently the most expensive (average of $336). 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 EPX?

Find hourly flight availability from Portland to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated april 3, 2025.

When flying from Portland, Maine to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated april 3, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and United Airlines from Portland to Caribbean Islands to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,274 reviews

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,274 reviews
Southwest
8.0
Very good
4,274 reviews

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,897 reviews
Southwest
8.0
Very good
4,274 reviews

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,616 reviews
Southwest
8.0
Very good
4,274 reviews

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
JetBlue
7.3
Good
2,922 reviews
Southwest
8.0
Very good
4,274 reviews

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,274 reviews

Overall

8.0

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

Find useful and relevant information for your journey from Portland to Caribbean Islands. 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 Islands?

    If you book a flight to Caribbean Islands from Portland, you will be flying from Portland, which is the city’s only airport. Portland (PWM) is located 2.9 mi from the center of Portland.

  • What are the cheapest airlines to fly from Portland, Maine to Caribbean Islands one-way?

    $121 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on United Airlines and Delta, with prices starting from $178 and $224, respectively.

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

    The most popular flight routes from Portland, Maine to Caribbean Islands are Portland - Oranjestad Reina Beatrix, Portland - San Juan Luis Munoz Marin Intl and Portland - Montego Bay Sangster Intl.

  • Can I find deals for flights from Portland to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Portland to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Caribbean Islands.

  • Can I find deals for business class flights from Portland to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Portland to Caribbean Islands 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 Islands?

    Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Caribbean Islands (average of $254). Flying from Portland, Maine to Caribbean Islands in December is currently the most expensive (average of $336). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
Boston to Las Vegas flights
Boston to Los Angeles flights
Boston to O'Hare Intl flights
Boston to Fort Lauderdale flights
Boston to Miami flights
Boston to Dallas/Fort Worth flights
Boston to Orlando flights
Boston to Reagan-National flights
Boston to Dulles Intl flights
Boston to Seattle flights
Boston to Tampa flights
Boston to Baltimore flights
Boston to San Francisco flights
Boston to Newark flights
Boston to Austin flights
Boston to Sky Harbor Intl flights
Boston to Philadelphia flights
Boston to LaGuardia flights
Boston to Denver flights
Boston to Nashville flights
Boston to Cancún flights
Boston to West Palm Beach flights
Boston to Charlotte flights
Boston to Hobby flights
Boston to Atlanta flights
Boston to Salt Lake City flights
Boston to San Diego flights
Boston to Charleston flights
Boston to New Orleans flights
Boston to Raleigh flights
Boston to Fort Myers flights
Boston to Sarasota flights
Boston to Minneapolis flights
Boston to Pittsburgh flights
Boston to George Bush Intcntl flights
Boston to Midway flights
Boston to John F Kennedy Intl flights
Boston to Ontario flights
Boston to Cincinnati flights
Boston to Mexico City flights
Boston to Pearson Intl flights
Boston to Savannah flights
Boston to Richmond flights
Boston to Detroit flights
Boston to Myrtle Beach flights
Boston to Indianapolis flights
Boston to Burbank flights
Boston to Portland flights
Boston to Honolulu flights
Boston to St. Louis flights

Top 6 airlines flying from Portland to Caribbean Islands

Discover the top 6 airlines that operate flights from Portland to Caribbean Islands. 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 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$229FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$214Average$555FlexibilityNo cancel feeOn-time62%
DeltaCheapest$274Average$522FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$301Average$628FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$305Average$703FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$401Average$796FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.