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Caribbean Islands

$87+ Cheap flights from Portland (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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Nov 9 — Nov 161
Sat 11/9
Sat 11/16
1 adult, Economy
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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 November 4, 2024.

This Mytrip deal was found by Cheapflights users on 11/3. 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 12/99:13 pmPWM - SJU
1 stop21h 18mFrontier
Tue 12/175:31 pmSJU - PWM
1 stop18h 41mFrontier
Deal found 11/3$152
This Delta deal was found by Cheapflights users on 11/3. 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 12/95:05 amPWM - SJU
1 stop8h 09mDelta
Fri 12/132:28 pmSJU - PWM
1 stop10h 31mDelta
Deal found 11/3$290
This American Airlines deal was found by Cheapflights users on 11/3. 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
2 stops15h 04mAmerican Airlines
Tue 12/172:19 pmSJU - PWM
2 stops10h 40mAmerican Airlines
Deal found 11/3$307
This United Airlines deal was found by Cheapflights users on 11/3. 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 12/96:00 amPWM - SJU
1 stop7h 40mUnited Airlines
Thu 12/122:05 amSJU - PWM
1 stop9h 12mUnited Airlines
Deal found 11/3$312
This Mytrip deal was found by Cheapflights users on 11/3. 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 - SJU
2 stops25h 26mMultiple Airlines
Thu 12/123:20 amSJU - PWM
3 stops33h 09mMultiple Airlines
Deal found 11/3$368
This Delta deal was found by Cheapflights users on 11/4. 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 11/4$379
This American Airlines deal was found by Cheapflights users on 11/3. 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 12/712:27 pmPWM - AUA
2 stops22h 48mAmerican Airlines
Thu 12/125:59 pmAUA - PWM
2 stops22h 27mAmerican Airlines
Deal found 11/3$395
This JetBlue deal was found by Cheapflights users on 11/4. 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.
Sat 11/163:33 pmPWM - SJU
1 stop7h 45mJetBlue
Wed 11/207:15 amSJU - PWM
1 stop8h 30mJetBlue
Deal found 11/4$416
This American Airlines deal was found by Cheapflights users on 11/4. 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 - NAS
2 stops13h 40mAmerican Airlines
Mon 12/1612:32 pmNAS - PWM
2 stops11h 27mAmerican Airlines
Deal found 11/4$421
This American Airlines deal was found by Cheapflights users on 11/3. 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 12/67:20 amPWM - PUJ
1 stop8h 25mAmerican Airlines
Tue 12/103:39 pmPUJ - PWM
2 stops21h 26mAmerican Airlines
Deal found 11/3$432
This United Airlines deal was found by Cheapflights users on 11/3. 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 - PUJ
1 stop21h 08mUnited Airlines
Tue 12/105:25 pmPUJ - PWM
1 stop18h 03mUnited Airlines
Deal found 11/3$434
This Mytrip deal was found by Cheapflights users on 11/3. 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 12/212:01 pmPWM - STT
2 stops21h 47mMultiple Airlines
Fri 12/611:56 amSTT - PWM
3 stops24h 33mMultiple Airlines
Deal found 11/3$442

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 2,455,398 searches. Data last updated November 4, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sun 11/17

8:12 pm-9:55 am

1 stop12h 43m

$87

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Sun 12/15

9:13 pm-1:33 pm

2 stops16h 20m

$138

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 1/28

5:44 am-9:59 pm

2 stops15h 15m

$145

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

Tue 1/7

5:20 am-1:50 pm

1 stop7h 30m

$164

PortlandProvidenciales

PWM - PLS

PWMPLS

Portland

Thu 1/2

6:05 am-1:52 pm

1 stop7h 47m

$221

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 2/12

12:03 pm-12:11 am

1 stop11h 08m

$329

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

Mon 12/16

9:13 pm-3:40 pm

2 stops17h 27m

$182

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

Wed 1/8

7:10 am-4:45 pm

1 stop8h 35m

$188

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Fri 12/6

6:14 pm-7:36 pm

3 stops24h 22m

$200

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 1/4

6:00 am-2:40 pm

1 stop7h 40m

$230

Flights are sorted by cheapest first

Deals found on 11/3

Showing 1-10 of 51 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 4, 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 4, 2024.
Peruse reviews from past customers who have flown with JetBlue, 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
5,089 reviews

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Boarding

8.3

Crew

8.7

Reviews

1 / 10

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

Southwest
8.1
Very good
5,089 reviews
Southwest
8.1
Very good
5,089 reviews

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Boarding

8.3

Crew

8.7

Reviews

1 / 10

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

Delta
8.0
Very good
8,829 reviews
Southwest
8.1
Very good
5,089 reviews

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Boarding

8.3

Crew

8.7

Reviews

1 / 10

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

JetBlue
7.5
Good
3,493 reviews
Southwest
8.1
Very good
5,089 reviews

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Boarding

8.3

Crew

8.7

Reviews

1 / 10

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

LATAM Airlines
7.5
Good
1,970 reviews
Southwest
8.1
Very good
5,089 reviews

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Boarding

8.3

Crew

8.7

Reviews

1 / 10

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

United Airlines
7.4
Good
9,226 reviews
Southwest
8.1
Very good
5,089 reviews

Entertainment

7.7

Food

7.2

Comfort

8.1

Overall

8.1

Boarding

8.3

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.

  • Can I find flights from Portland, Maine to Caribbean Islands for under $200 on Cheapflights?

    Yes, there are multiple flights from Portland, Maine to Caribbean Islands for under $200. The cheapest flight booked recently is on Frontier for just $152, but on average you can expect to pay $388.

  • Are there last-minute flights available from Portland, Maine to Caribbean Islands for under $500?

    There are currently 7+ open flights from Portland, Maine to Caribbean Islands within the next 7 days for less than $500.

  • What are the cheapest airlines to fly from Portland, Maine to Caribbean Islands one-way?

    $87 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on American Airlines and United Airlines, with prices starting from $145 and $164, 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 - Saint Thomas Island Cyril E King.

  • What does PWM to SJU mean?

    PWM stands for Portland Airport, while SJU stands for San Juan Luis Munoz Marin Intl Airport. These codes are often called IATA codes, a set of identifiers established by IATA (International Air Transport Association) that is widely used by airlines and the aviation industry. Punta Cana Airport (PUJ), Santo Domingo Las Americas Airport (SDQ), Montego Bay Sangster Intl Airport (MBJ), Oranjestad Reina Beatrix Airport (AUA), Santiago de los Caballeros Airport (STI) are other airports near this flight route and their unique identifiers/IATA codes.

  • Can I find deals for flights from Portland to Caribbean Islands that include extra baggage allowance?

    The amount of baggage you can bring on your Portland to Caribbean Islands flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Portland to Caribbean Islands with specific airlines?

    Yes, Cheapflights allows you to browse and filter Portland to Caribbean Islands flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Portland to Caribbean Islands that allow pets onboard?

    Many airlines flying from Portland to Caribbean Islands offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Portland to Caribbean Islands?

    Yes, you can often find last-minute deals on Portland to Caribbean Islands flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Portland, Maine to Caribbean Islands flight deals updated?

    The Portland, Maine to Caribbean Islands flight deals you see on this page were last updated on 11/4.

  • 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.

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Top 5 airlines flying from Portland to Caribbean Islands

Discover the top 5 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 2,455,398 searches. Data last updated November 4, 2024.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$214Average$582FlexibilityNo cancel feeOn-time62%
FrontierCheapest$228Average$287FlexibilityNo cancel feeOn-time62%
DeltaCheapest$271Average$543FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$308Average$679FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$322Average$639FlexibilityNo cancel feeOn-time71%
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