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Caribbean Islands

$66+ 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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Dec 29 — Jan 51
Sun 12/29
Sun 1/5
1 adult, Economy
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Cheap flight deals from Portland to Caribbean Islands

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to Caribbean Islands (zzEPX). 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 December 24, 2024.

Round-trip from

$144
(Mytrip)

One-way from

$66
(Mytrip)
From Portland to Caribbean Islands
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One-way flight from Portland to Caribbean Islands
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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 December 24, 2024.

This Delta deal was found by Cheapflights users on 12/24. 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.
Mon 12/306:05 amPWM - SJU
1 stop10h 10mDelta
Tue 1/77:00 amSJU - PWM
1 stop8h 22mDelta
Deal found 12/24$722
This American Airlines deal was found by Cheapflights users on 12/24. 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.
Mon 12/305:39 amPWM - SJU
1 stop6h 55mAmerican Airlines
Tue 1/77:45 amSJU - PWM
2 stops17h 12mAmerican Airlines
Deal found 12/24$754
This American Airlines deal was found by Cheapflights users on 12/23. 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.
Mon 12/235:17 pmPWM - GCM
2 stops18h 43mAmerican Airlines
Sat 12/2812:55 pmGCM - PWM
2 stops10h 06mAmerican Airlines
Deal found 12/23$769
This United Airlines deal was found by Cheapflights users on 12/23. 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.
Mon 12/304:05 pmPWM - SJU
1 stop7h 31mUnited Airlines
Mon 1/62:05 amSJU - PWM
2 stops13h 37mUnited Airlines
Deal found 12/23$839
This United deal was found by Cheapflights users on 12/23. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/237:16 pmPWM - GCM
1 stop21h 14mUnited Airlines
Sat 12/282:40 pmGCM - PWM
1 stop23h 57mUnited Airlines
Deal found 12/23$952
This American Airlines deal was found by Cheapflights users on 12/23. 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.
Thu 12/265:08 pmPWM - SXM
2 stops22h 01mAmerican Airlines
Wed 1/295:19 pmSXM - PWM
2 stops21h 35mAmerican Airlines
Deal found 12/23$1,799
This Delta deal was found by Cheapflights users on 12/23. 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.
Thu 12/266:05 amPWM - SXM
1 stop8h 06mDelta
Wed 1/291:40 pmSXM - PWM
1 stop11h 11mDelta
Deal found 12/23$2,217

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 December 24, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 2/10

9:02 pm-11:30 am

1 stop13h 28m

San Juan Luis Munoz Marin Intl

Mon 2/24

6:35 am-7:35 pm

1 stop14h 00m

$144

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 2/25

5:27 am-1:01 pm

1 stop6h 34m

San Juan Luis Munoz Marin Intl

Thu 3/6

7:00 am-2:22 pm

1 stop8h 22m

$284

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 1/25

5:44 am-10:07 pm

2 stops15h 23m

San Juan Luis Munoz Marin Intl

Tue 1/28

6:00 am-12:10 pm

1 stop7h 10m

$300

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 4/30

10:15 am-6:12 pm

1 stop7h 57m

San Juan Luis Munoz Marin Intl

Wed 5/7

3:13 am-9:27 am

1 stop6h 14m

$347

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 1/27

6:00 am-2:40 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Fri 1/31

2:05 am-10:32 am

1 stop9h 27m

$374

PortlandNassau

PWM - NAS

PWMNAS

Portland

Wed 4/23

5:45 am-10:49 am

1 stop5h 04m

Nassau Intl

Tue 4/29

11:39 am-11:46 pm

1 stop12h 07m

$399

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

Tue 1/21

5:23 am-1:55 pm

1 stop7h 32m

Oranjestad Reina Beatrix

Sat 1/25

4:35 pm-11:51 pm

1 stop8h 16m

$408

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

Tue 1/21

7:10 am-4:55 pm

1 stop8h 45m

Oranjestad Reina Beatrix

Sat 1/25

5:45 pm-12:06 pm

2 stops19h 21m

$413

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Fri 2/21

6:18 pm-11:25 pm

2 stops28h 07m

San Juan Luis Munoz Marin Intl

Wed 2/26

8:30 pm-4:43 pm

2 stops21h 13m

$417

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Sat 2/1

5:44 am-2:25 pm

1 stop8h 41m

Montego Bay Sangster Intl

Thu 2/6

11:35 am-10:30 pm

1 stop10h 55m

$422

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/23

Showing 1-10 of 45 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 $380). 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 December 24, 2024.

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 December 24, 2024.
Peruse reviews from past customers who have flown with Delta, Frontier and American 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
4,765 reviews

Entertainment

7.7

Food

7.2

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

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
4,765 reviews
Southwest
8.1
Very good
4,765 reviews

Entertainment

7.7

Food

7.2

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

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
8,580 reviews
Southwest
8.1
Very good
4,765 reviews

Entertainment

7.7

Food

7.2

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

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
1,865 reviews
Southwest
8.1
Very good
4,765 reviews

Entertainment

7.7

Food

7.2

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

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
3,260 reviews
Southwest
8.1
Very good
4,765 reviews

Entertainment

7.7

Food

7.2

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

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
9,009 reviews
Southwest
8.1
Very good
4,765 reviews

Entertainment

7.7

Food

7.2

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

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 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?

    $66 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on United Airlines and American Airlines, with prices starting from $142 and $150, 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 - Oranjestad Reina Beatrix 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 March is currently the most expensive (average of $380). 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.

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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 December 24, 2024.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$214Average$586FlexibilityNo cancel feeOn-time62%
FrontierCheapest$228Average$284FlexibilityNo cancel feeOn-time62%
DeltaCheapest$271Average$551FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$305Average$756FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$322Average$630FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$371Average$661FlexibilityNo cancel feeOn-time63%
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