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$141+ Cheap flights from Portland (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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
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 November 20, 2024.

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 November 20, 2024.

This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/89:13 pmPWM - SJU
1 stop28h 27mFrontier
Tue 12/1710:28 amSJU - PWM
1 stop25h 44mFrontier
Deal found 11/19$181
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.
Tue 12/102:55 pmPWM - SJU
1 stop9h 04mDelta
Tue 12/173:30 pmSJU - PWM
1 stop9h 00mDelta
Deal found 11/19$300
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/105:50 amPWM - SJU
1 stop17h 00mAmerican Airlines
Tue 12/1712:50 pmSJU - PWM
2 stops10h 56mAmerican Airlines
Deal found 11/19$317
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/35:50 amPWM - AUA
1 stop7h 25mAmerican Airlines
Wed 12/112:55 pmAUA - PWM
1 stop8h 51mAmerican Airlines
Deal found 11/19$401
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.
Mon 12/95:56 pmPWM - MBJ
2 stops19h 37mMultiple Airlines
Tue 12/172:38 pmMBJ - PWM
3 stops27h 27mMultiple Airlines
Deal found 11/20$427
This United 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/96:00 amPWM - SJU
1 stop7h 40mUnited Airlines
Sun 12/152:05 amSJU - PWM
1 stop9h 12mUnited Airlines
Deal found 11/19$430
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.
Tue 12/35:00 amPWM - AUA
1 stop7h 55mDelta
Thu 12/124:35 pmAUA - PWM
1 stop8h 33mDelta
Deal found 11/19$437
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.
Mon 12/97:27 pmPWM - MBJ
2 stops19h 02mUnited Airlines
Tue 12/173:36 pmMBJ - PWM
2 stops18h 52mUnited Airlines
Deal found 11/20$452
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.
Sat 12/76:05 amPWM - NAS
1 stop10h 00mDelta
Sat 12/142:54 pmNAS - PWM
1 stop9h 14mDelta
Deal found 11/20$458
This United Airlines deal was found by Cheapflights users on 11/18. 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 12/127:27 pmPWM - PUJ
1 stop21h 08mUnited Airlines
Tue 12/171:00 pmPUJ - PWM
1 stop22h 28mUnited Airlines
Deal found 11/18$459
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/36:00 amPWM - AUA
1 stop9h 25mUnited Airlines
Wed 12/115:35 pmAUA - PWM
2 stops17h 42mUnited Airlines
Deal found 11/19$473
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

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

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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

Sat 1/25

1:38 pm-10:22 pm

1 stop7h 44m

San Juan Luis Munoz Marin Intl

Fri 1/31

2:05 am-10:32 am

1 stop9h 27m

$301

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

4:50 pm-11:40 am

2 stops17h 50m

Punta Cana

Mon 1/13

5:05 pm-12:06 pm

2 stops20h 01m

$388

PortlandNassau

PWM - NAS

PWMNAS

Portland

Wed 3/26

5:51 am-11:29 am

1 stop5h 38m

Nassau Intl

Wed 4/2

2:14 pm-12:28 am

1 stop10h 14m

$389

PortlandNassau

PWM - NAS

PWMNAS

Portland

Thu 4/3

6:10 am-5:28 pm

1 stop11h 18m

Nassau Intl

Tue 4/8

1:50 pm-11:01 pm

1 stop9h 11m

$399

PortlandPunta Cana

PWM - PUJ

PWMPUJ

Portland

Thu 1/30

6:35 pm-1:41 pm

1 stop18h 06m

Punta Cana

Thu 2/6

1:00 pm-10:28 am

1 stop22h 28m

$400

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 57 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 $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 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 November 20, 2024.

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 November 20, 2024.
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

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

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

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

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

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

LATAM Airlines
7.5
Good
1,934 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

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

JetBlue
7.5
Good
3,394 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

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

United Airlines
7.4
Good
9,171 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

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. 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 $141 on Delta. Other airlines that offer cheap prices include American Airlines from $150 and United Airlines from $185 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 - Punta Cana.

  • 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 $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

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 2,629,791 searches. Data last updated November 20, 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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