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$94+ 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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Cheap flight deals from Portland to Caribbean

Keep the following information in mind while searching for Portland to Caribbean flight deals. Data was last updated February 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
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One-way flight from Portland to Caribbean
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

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 February 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.
Sat 3/810:08 amPWM - SJU
1 stop21h 27mFrontier
Thu 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.
Tue 4/15:35 pmPWM - SJU
1 stop7h 57mJetBlue
Mon 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.
Sat 4/262:59 pmPWM - SJU
1 stop8h 49mDelta
Tue 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.
Fri 5/212:50 pmPWM - SJU
1 stop11h 19mAmerican Airlines
Tue 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.
Fri 2/2812:06 pmPWM - SJU
2 stops34h 36mMultiple Airlines
Fri 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.
Sat 3/110:23 amPWM - PUJ
2 stops25h 51mFrontier
Thu 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.
Tue 4/16:15 amPWM - SJU
2 stops14h 23mUnited Airlines
Mon 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.
Sun 3/305:35 pmPWM - SDQ
1 stop7h 38mJetBlue
Thu 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.
Wed 3/55:34 amPWM - AUA
1 stop8h 46mDelta
Tue 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.
Thu 4/36:10 amPWM - AUA
1 stop10h 15mJetBlue
Thu 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.
Tue 3/112:21 pmPWM - AUA
2 stops21h 09mAmerican Airlines
Wed 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.
Wed 3/195:20 pmPWM - MBJ
2 stops17h 15mAmerican Airlines
Wed 3/2610:15 amMBJ - PWM
2 stops12h 32mAmerican Airlines
Deal found 2/20$411

Find flights from Portland to Caribbean within your budget

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 February 20, 2025.

Fly from

Portland

Fly to

Caribbean

Route

Depart

Return

Price

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 3/8

10:08 am-8:35 am

1 stop21h 27m

San Juan Luis Munoz Marin Intl

Thu 3/27

12:55 pm-7:35 pm

1 stop30h 40m

$178

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 4/1

5:35 pm-2:46 am

1 stop9h 11m

San Juan Luis Munoz Marin Intl

Sat 4/5

7:00 am-4:40 pm

1 stop9h 40m

$248

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 4/1

5:30 am-2:12 pm

1 stop8h 42m

San Juan Luis Munoz Marin Intl

Sat 4/5

7:40 am-2:28 pm

1 stop6h 48m

$295

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Fri 5/2

12:50 pm-12:09 am

1 stop11h 19m

San Juan Luis Munoz Marin Intl

Tue 5/6

5:45 am-3:31 pm

1 stop9h 46m

$311

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 4/9

8:07 pm-6:44 pm

2 stops22h 37m

San Juan Luis Munoz Marin Intl

Mon 4/14

2:40 pm-5:27 pm

2 stops26h 47m

$333

PortlandSanto Domingo

PWM - SDQ

PWMSDQ

Portland

Sun 3/30

5:35 pm-1:13 am

1 stop7h 38m

Santo Domingo Las Americas

Thu 4/3

9:57 am-11:19 pm

1 stop13h 22m

$382

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 3/8

3:55 pm-12:36 am

1 stop7h 41m

San Juan Luis Munoz Marin Intl

Wed 3/26

1:05 am-2:52 pm

2 stops13h 47m

$390

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

Wed 3/5

5:34 am-3:20 pm

1 stop8h 46m

Oranjestad Reina Beatrix

Wed 3/12

2:10 pm-12:15 am

1 stop10h 05m

$401

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

Thu 4/3

6:10 am-4:25 pm

1 stop10h 15m

Oranjestad Reina Beatrix

Thu 4/10

1:25 pm-11:00 pm

1 stop9h 35m

$405

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

Tue 3/11

5:42 am-4:00 pm

2 stops10h 18m

Oranjestad Reina Beatrix

Wed 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

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.

Travel insights for flights from Portland to Caribbean

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

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

Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Caribbean (average of $254). Flying from Portland, Maine to Caribbean 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 CB?

Find hourly flight availability from Portland to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 20, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Portland, Maine to Caribbean as you normally would.

Rainfall in Caribbean by month

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

In terms of precipitation, rainfall in Caribbean 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 when rainfall is around 2.2 in.

Temperature in Caribbean by month

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

If weather is an important factor for your trip to Caribbean, 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

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 February 20, 2025.
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. 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.

  • 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 $115 on JetBlue. Other airlines that offer cheap prices include American Airlines from $156 and United Airlines from $197 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 - Saint Thomas Island Cyril E King and Portland - Oranjestad Reina Beatrix.

  • 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, September is the cheapest month in which you can book a flight from Portland, Maine to Caribbean (average of $254). Flying from Portland, Maine to Caribbean 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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Alternative routes for Portland to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Portland to Caribbean

Discover the top 6 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 February 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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