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Caribbean Islands

$94+ 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
feb. 25 — mar. 41
mar. 2/25
mar. 3/4
1 adult, Economy
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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 febrero 20, 2025.

Round-trip from

$178
(Mytrip)

One-way from

$115
(JetBlue Airways)

Popular in

April

Cheapest in

September

Average price

$594
From Portland to Caribbean Islands
Search Deals
One-way flight from Portland to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($66 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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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 febrero 20, 2025.

This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 3/810:08 amPWM - SJU
1 stop21h 27mFrontier
jue. 3/2712:55 pmSJU - PWM
1 stop30h 40mFrontier
Deal found 2/19$178
This JetBlue deal was found by Cheapflights users on 2/20. 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.
mar. 4/15:35 pmPWM - SJU
1 stop7h 57mJetBlue
lun. 4/712:57 pmSJU - PWM
1 stop10h 03mJetBlue
Deal found 2/20$229
This Delta deal was found by Cheapflights users on 2/19. 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.
sáb. 4/262:59 pmPWM - SJU
1 stop8h 49mDelta
mar. 5/66:35 amSJU - PWM
1 stop7h 44mDelta
Deal found 2/19$295
This American Airlines deal was found by Cheapflights users on 2/20. 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.
vie. 5/212:50 pmPWM - SJU
1 stop11h 19mAmerican Airlines
mar. 5/65:45 amSJU - PWM
1 stop17h 01mAmerican Airlines
Deal found 2/20$311
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/2812:06 pmPWM - SJU
2 stops34h 36mMultiple Airlines
vie. 3/711:27 amSJU - PWM
3 stops33h 00mMultiple Airlines
Deal found 2/20$322
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 3/110:23 amPWM - PUJ
2 stops25h 51mFrontier
jue. 3/62:24 pmPUJ - PWM
2 stops30h 11mFrontier
Deal found 2/19$340
This United Airlines deal was found by Cheapflights users on 2/20. 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.
mar. 4/16:15 amPWM - SJU
2 stops14h 23mUnited Airlines
lun. 4/74:55 pmSJU - PWM
1 stop6h 32mUnited Airlines
Deal found 2/20$350
This JetBlue deal was found by Cheapflights users on 2/19. 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.
dom. 3/305:35 pmPWM - SDQ
1 stop7h 38mJetBlue
jue. 4/39:57 amSDQ - PWM
1 stop13h 22mJetBlue
Deal found 2/19$382
This Delta deal was found by Cheapflights users on 2/20. 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.
mié. 3/55:34 amPWM - AUA
1 stop8h 46mDelta
mar. 3/112:10 pmAUA - PWM
1 stop10h 05mDelta
Deal found 2/20$401
This JetBlue Airways deal was found by Cheapflights users on 2/19. 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.
jue. 4/36:10 amPWM - AUA
1 stop10h 15mJetBlue
jue. 4/101:25 pmAUA - PWM
1 stop9h 35mJetBlue
Deal found 2/19$405
This American Airlines deal was found by Cheapflights users on 2/20. 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.
mar. 3/112:21 pmPWM - AUA
2 stops21h 09mAmerican Airlines
mié. 3/194:45 pmAUA - PWM
2 stops19h 20mAmerican Airlines
Deal found 2/20$406
This American Airlines deal was found by Cheapflights users on 2/20. 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.
mié. 3/195:20 pmPWM - MBJ
2 stops17h 15mAmerican Airlines
mié. 3/2610:15 amMBJ - PWM
2 stops12h 32mAmerican Airlines
Deal found 2/20$411

Find flights from Portland to Caribbean Islands within your budget

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 febrero 20, 2025.

Fly from

Portland

Fly to

Caribbean Islands

Route

Depart

Return

Price

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

sáb. 3/8

10:08 am-8:35 am

1 stop21h 27m

San Juan Luis Munoz Marin Intl

jue. 3/27

12:55 pm-7:35 pm

1 stop30h 40m

$178

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

mar. 4/1

5:35 pm-2:46 am

1 stop9h 11m

San Juan Luis Munoz Marin Intl

sáb. 4/5

7:00 am-4:40 pm

1 stop9h 40m

$248

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

mar. 4/1

5:30 am-2:12 pm

1 stop8h 42m

San Juan Luis Munoz Marin Intl

sáb. 4/5

7:40 am-2:28 pm

1 stop6h 48m

$295

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

vie. 5/2

12:50 pm-12:09 am

1 stop11h 19m

San Juan Luis Munoz Marin Intl

mar. 5/6

5:45 am-3:31 pm

1 stop9h 46m

$311

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

mié. 4/9

8:07 pm-6:44 pm

2 stops22h 37m

San Juan Luis Munoz Marin Intl

lun. 4/14

2:40 pm-5:27 pm

2 stops26h 47m

$333

PortlandSanto Domingo

PWM - SDQ

PWMSDQ

Portland

dom. 3/30

5:35 pm-1:13 am

1 stop7h 38m

Santo Domingo Las Americas

jue. 4/3

9:57 am-11:19 pm

1 stop13h 22m

$382

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

sáb. 3/8

3:55 pm-12:36 am

1 stop7h 41m

San Juan Luis Munoz Marin Intl

mié. 3/26

1:05 am-2:52 pm

2 stops13h 47m

$390

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

mié. 3/5

5:34 am-3:20 pm

1 stop8h 46m

Oranjestad Reina Beatrix

mié. 3/12

2:10 pm-12:15 am

1 stop10h 05m

$401

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

jue. 4/3

6:10 am-4:25 pm

1 stop10h 15m

Oranjestad Reina Beatrix

jue. 4/10

1:25 pm-11:00 pm

1 stop9h 35m

$405

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

mar. 3/11

5:42 am-4:00 pm

2 stops10h 18m

Oranjestad Reina Beatrix

mié. 3/19

5:00 pm-1:49 pm

2 stops20h 49m

$406

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 47 results
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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.

Travel insights for flights from Portland to Caribbean Islands

Get recent, data-driven insights about flights from Portland to Caribbean Islands including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $363). 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 febrero 20, 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 febrero 20, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and LATAM 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
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

LATAM Airlines
7.5
Good
1,795 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Food

7.1

Comfort

8.1

Overall

8.1

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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?

    $115 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on American Airlines and United Airlines, with prices starting from $156 and $197, 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 - San Juan Luis Munoz Marin Intl, Portland - Saint Thomas Island Cyril E King and Portland - Oranjestad Reina Beatrix.

  • 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 March is currently the most expensive (average of $363). 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

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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 febrero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$148Average$278FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$214Average$551FlexibilityNo cancel feeOn-time62%
DeltaCheapest$274Average$537FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$305Average$734FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$320Average$640FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$401Average$711FlexibilityNo cancel feeOn-time63%
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