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$149+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
ene. 22 — ene. 291
mié. 1/22
mié. 1/29
1 adult, Economy
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Cheap flight deals from Portland to Caribbean

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to Caribbean (0CB). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated enero 17, 2025.

Round-trip from

$290
(FlightHub)

One-way from

$149
(JetBlue)
From Portland to Caribbean
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One-way flight from Portland to Caribbean
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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 enero 17, 2025.

This FlightHub deal was found by Cheapflights users on 1/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 2/27:06 pmPWM - SJU
1 stop14h 31mFrontier
lun. 2/106:00 amSJU - PWM
1 stop13h 33mFrontier
Deal found 1/16$290
This Mytrip deal was found by Cheapflights users on 1/16. 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.
lun. 3/36:18 pmPWM - SJU
2 stops21h 09mMultiple Airlines
mar. 3/115:45 pmSJU - PWM
2 stops25h 42mMultiple Airlines
Deal found 1/16$291
This Delta deal was found by Cheapflights users on 1/16. 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.
mar. 2/253:04 pmPWM - SJU
1 stop7h 55mDelta
mar. 3/111:16 pmSJU - PWM
1 stop10h 54mDelta
Deal found 1/16$295
This JetBlue deal was found by Cheapflights users on 1/15. 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.
mié. 4/305:50 pmPWM - SJU
1 stop9h 08mJetBlue
jue. 5/87:50 amSJU - PWM
1 stop9h 05mJetBlue
Deal found 1/15$321
This American Airlines deal was found by Cheapflights users on 1/16. 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.
lun. 3/37:20 amPWM - SJU
1 stop14h 15mAmerican Airlines
mar. 3/115:00 amSJU - PWM
1 stop7h 25mAmerican Airlines
Deal found 1/16$326
This United Airlines deal was found by Cheapflights users on 1/16. 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.
dom. 2/21:38 pmPWM - SJU
1 stop7h 44mUnited Airlines
vie. 2/72:05 amSJU - PWM
1 stop9h 27mUnited Airlines
Deal found 1/16$358
This Southwest deal was found by Cheapflights users on 1/15. 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.
mié. 2/51:05 pmPWM - SJU
1 stop10h 20mSouthwest
mié. 2/126:00 amSJU - PWM
1 stop7h 30mSouthwest
Deal found 1/15$384
This American Airlines deal was found by Cheapflights users on 1/15. 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. 2/75:44 amPWM - NAS
1 stop6h 52mAmerican Airlines
dom. 2/1612:35 pmNAS - PWM
1 stop9h 50mAmerican Airlines
Deal found 1/15$411
This Delta deal was found by Cheapflights users on 1/16. 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. 3/55:27 amPWM - AUA
1 stop7h 28mDelta
mar. 3/112:10 pmAUA - PWM
1 stop10h 00mDelta
Deal found 1/16$419
This American Airlines deal was found by Cheapflights users on 1/16. 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.
lun. 1/274:50 pmPWM - AUA
2 stops20h 45mAmerican Airlines
mié. 2/55:45 pmAUA - PWM
2 stops19h 30mAmerican Airlines
Deal found 1/16$424
This American Airlines deal was found by Cheapflights users on 1/16. 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.
jue. 3/274:11 pmPWM - MBJ
2 stops18h 24mAmerican Airlines
mié. 4/210:15 amMBJ - PWM
1 stop11h 29mAmerican Airlines
Deal found 1/16$435
This Delta deal was found by Cheapflights users on 1/16. 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. 4/235:40 amPWM - NAS
1 stop7h 35mDelta
mar. 4/294:50 pmNAS - PWM
1 stop7h 09mDelta
Deal found 1/16$437

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 enero 17, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

dom. 2/2

7:06 pm-10:37 am

1 stop14h 31m

San Juan Luis Munoz Marin Intl

lun. 2/10

6:00 am-6:33 pm

1 stop13h 33m

$290

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

lun. 3/3

6:18 pm-4:27 pm

2 stops21h 09m

San Juan Luis Munoz Marin Intl

mar. 3/11

5:45 pm-7:27 pm

2 stops25h 42m

$291

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

mar. 2/25

5:27 am-1:01 pm

1 stop6h 34m

San Juan Luis Munoz Marin Intl

jue. 3/6

7:00 am-2:22 pm

1 stop8h 22m

$295

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

mié. 4/30

10:15 am-6:12 pm

1 stop7h 57m

San Juan Luis Munoz Marin Intl

mié. 5/7

3:13 am-9:27 am

1 stop6h 14m

$321

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

lun. 3/3

7:20 am-10:35 pm

1 stop14h 15m

San Juan Luis Munoz Marin Intl

mar. 3/11

5:00 am-12:25 pm

1 stop7h 25m

$326

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

dom. 2/2

1:38 pm-10:22 pm

1 stop7h 44m

San Juan Luis Munoz Marin Intl

vie. 2/7

2:05 am-10:32 am

1 stop9h 27m

$358

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

mié. 2/5

1:05 pm-12:25 am

1 stop10h 20m

San Juan Luis Munoz Marin Intl

mié. 2/12

6:00 am-12:30 pm

1 stop7h 30m

$384

PortlandNassau

PWM - NAS

PWMNAS

Portland

vie. 2/7

5:44 am-12:36 pm

1 stop6h 52m

Nassau Intl

dom. 2/16

12:35 pm-10:25 pm

1 stop9h 50m

$411

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

mar. 3/11

5:29 am-12:55 pm

1 stop7h 26m

Oranjestad Reina Beatrix

mié. 3/19

3:35 pm-11:56 pm

1 stop8h 21m

$419

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

mié. 2/5

7:10 am-4:55 pm

1 stop8h 45m

Oranjestad Reina Beatrix

dom. 2/9

5:55 pm-10:30 pm

1 stop29h 35m

$428

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

Showing 1-10 of 45 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 $378). 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 enero 17, 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 enero 17, 2025.
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,511 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

LATAM Airlines
7.5
Good
1,847 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,199 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,964 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.7

Food

7.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $149 on JetBlue. Other airlines that offer cheap prices include Delta from $152 and American Airlines from $180 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 - Oranjestad Reina Beatrix and Portland - Montego Bay Sangster Intl.

  • 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 $378). 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 enero 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$148Average$284FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$214Average$576FlexibilityNo cancel feeOn-time62%
DeltaCheapest$274Average$559FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$305Average$738FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$322Average$626FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$371Average$661FlexibilityNo cancel feeOn-time63%
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