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Caribbean Islands

$150+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
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 November 21, 2024.

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 November 21, 2024.

This Booking.com deal was found by Cheapflights users on 11/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/69:13 pmPWM - SJU
1 stop28h 27mFrontier
Sun 12/83:03 pmSJU - PWM
1 stop30h 11mFrontier
Deal found 11/20$295
This Delta deal was found by Cheapflights users on 11/19. 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.
Sun 12/85:00 amPWM - SJU
1 stop7h 03mDelta
Fri 12/136:32 pmSJU - PWM
1 stop6h 27mDelta
Deal found 11/19$350
This United Airlines deal was found by Cheapflights users on 11/21. 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.
Sun 12/86:00 amPWM - SJU
1 stop7h 40mUnited Airlines
Thu 12/122:05 amSJU - PWM
1 stop9h 12mUnited Airlines
Deal found 11/21$404
This American Airlines deal was found by Cheapflights users on 11/20. 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 12/65:50 amPWM - SJU
1 stop17h 00mAmerican Airlines
Mon 12/92:19 pmSJU - PWM
2 stops9h 27mAmerican Airlines
Deal found 11/20$452
This Delta deal was found by Cheapflights users on 11/21. 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 12/76:05 amPWM - NAS
1 stop10h 00mDelta
Sat 12/145:20 pmNAS - PWM
1 stop6h 48mDelta
Deal found 11/21$458
This Delta deal was found by Cheapflights users on 11/20. 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.
Sun 12/85:00 amPWM - PUJ
1 stop7h 49mDelta
Thu 12/122:05 pmPUJ - PWM
1 stop11h 03mDelta
Deal found 11/20$469
This United Airlines deal was found by Cheapflights users on 11/20. 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.
Sun 12/86:00 amPWM - PUJ
1 stop9h 15mUnited Airlines
Thu 12/121:00 pmPUJ - PWM
2 stops10h 50mUnited Airlines
Deal found 11/20$471
This Mytrip deal was found by Cheapflights users on 11/20. 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 12/65:56 pmPWM - SJU
3 stops27h 34mMultiple Airlines
Sat 12/73:20 amSJU - PWM
3 stops33h 01mMultiple Airlines
Deal found 11/20$473
This American Airlines deal was found by Cheapflights users on 11/20. 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.
Sun 12/85:50 amPWM - PUJ
2 stops9h 15mAmerican Airlines
Thu 12/121:00 pmPUJ - PWM
2 stops10h 46mAmerican Airlines
Deal found 11/20$474
This American Airlines deal was found by Cheapflights users on 11/21. 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 12/512:56 pmPWM - AUA
1 stop24h 19mAmerican Airlines
Mon 12/91:20 pmAUA - PWM
1 stop10h 04mAmerican Airlines
Deal found 11/21$514
This United Airlines deal was found by Cheapflights users on 11/21. 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.
Thu 12/57:27 pmPWM - AUA
2 stops44h 23mUnited Airlines
Mon 12/95:35 pmAUA - PWM
2 stops22h 00mUnited Airlines
Deal found 11/21$531
This American Airlines deal was found by Cheapflights users on 11/21. 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.
Sat 12/75:50 amPWM - NAS
2 stops13h 40mAmerican Airlines
Sat 12/142:45 pmNAS - PWM
2 stops8h 01mAmerican Airlines
Deal found 11/21$532

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 2,612,795 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 1/13

7:37 pm-3:19 pm

1 stop18h 42m

San Juan Luis Munoz Marin Intl

Fri 1/17

6:00 am-6:48 pm

1 stop13h 48m

$163

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 1/21

5:35 am-2:20 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Tue 1/28

7:00 am-2:22 pm

1 stop8h 22m

$300

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 1/13

1:55 pm-10:22 pm

1 stop7h 27m

San Juan Luis Munoz Marin Intl

Thu 1/16

2:05 am-10:31 am

1 stop9h 26m

$311

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 1/18

5:44 am-11:58 pm

1 stop17h 14m

San Juan Luis Munoz Marin Intl

Sat 1/25

6:15 am-8:11 pm

2 stops14h 56m

$317

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 4/28

5:30 pm-12:57 am

1 stop7h 27m

San Juan Luis Munoz Marin Intl

Wed 4/30

3:13 am-9:27 am

1 stop6h 14m

$327

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Fri 1/24

6:18 pm-12:48 am

3 stops29h 30m

San Juan Luis Munoz Marin Intl

Sun 1/26

10:09 pm-5:10 pm

2 stops20h 01m

$371

PortlandPunta Cana

PWM - PUJ

PWMPUJ

Portland

Thu 1/9

2:24 pm-11:40 am

2 stops20h 16m

Punta Cana

Mon 1/13

5:50 pm-1:54 pm

2 stops21h 04m

$388

PortlandNassau

PWM - NAS

PWMNAS

Portland

Sat 2/1

6:00 am-11:53 am

1 stop5h 53m

Nassau Intl

Fri 2/28

2:55 pm-11:15 pm

1 stop8h 20m

$389

PortlandNassau

PWM - NAS

PWMNAS

Portland

Sat 1/18

5:44 am-7:15 pm

2 stops13h 31m

Nassau Intl

Sat 1/25

1:26 pm-8:11 pm

1 stop6h 45m

$394

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Fri 1/10

3:35 pm-12:25 am

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Wed 1/15

6:50 am-3:00 pm

2 stops9h 10m

$404

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 46 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 $335). 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 November 21, 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 November 21, 2024.
Peruse reviews from past customers who have flown with Frontier, 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
8.1
Very good
5,005 reviews

Boarding

8.2

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,005 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,755 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Copa Airlines
7.8
Good
1,779 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

LATAM Airlines
7.5
Good
1,932 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

JetBlue
7.5
Good
3,389 reviews
Southwest
8.1
Very good
5,005 reviews

Boarding

8.2

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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?

    $150 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 Frontier and Delta, with prices starting from $195 and $200, 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 - Punta Cana.

  • 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 $335). 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 Islands

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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 2,612,795 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$214Average$571FlexibilityNo cancel feeOn-time62%
FrontierCheapest$228Average$284FlexibilityNo cancel feeOn-time62%
DeltaCheapest$271Average$531FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$308Average$772FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$322Average$624FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$371Average$661FlexibilityNo cancel feeOn-time63%
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