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Jamaica

$142+ Cheap flights from Portland, ME (PWM) to Jamaica

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 1/2. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MBJ
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Portland to Jamaica

Cheapest flights from Portland to Jamaica
Explore the most affordable flight options available from Portland to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This Delta deal was found by Cheapflights users on 12/11. 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.
Wed 12/245:45 amPWM - MBJ
1 stop14h 56mDelta
Wed 12/318:00 amMBJ - PWM
1 stop14h 43mDelta
Deal found 12/11$355
This Delta deal was found by Cheapflights users on 12/10. 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 12/225:45 amPWM - MBJ
1 stop14h 56mDelta
Mon 12/292:23 pmMBJ - PWM
1 stop8h 20mDelta
Deal found 12/10$504
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/226:41 pmPWM - MBJ
2 stops18h 42mAmerican Airlines
Mon 12/291:25 pmMBJ - PWM
1 stop9h 26mAmerican Airlines
Deal found 12/11$574
This United Airlines deal was found by Cheapflights users on 12/10. 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.
Wed 12/247:30 pmPWM - MBJ
2 stops18h 30mUnited Airlines
Wed 12/313:20 pmMBJ - PWM
2 stops32h 39mUnited Airlines
Deal found 12/10$579
This Delta deal was found by Cheapflights users on 12/11. 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.
Wed 12/245:45 amPWM - MBJ
1 stop14h 56mDelta
Mon 1/52:19 pmMBJ - PWM
1 stop8h 35mDelta
Deal found 12/11$627
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/186:40 pmPWM - MBJ
2 stops18h 43mAmerican Airlines
Thu 12/251:12 pmMBJ - PWM
1 stop29h 04mAmerican Airlines
Deal found 12/11$656
This American Airlines deal was found by Cheapflights users on 12/10. 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.
Wed 12/245:20 pmPWM - MBJ
2 stops19h 05mAmerican Airlines
Wed 12/313:14 pmMBJ - PWM
1 stop7h 37mAmerican Airlines
Deal found 12/10$664
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/116:40 pmPWM - KIN
2 stops18h 02mAmerican Airlines
Wed 12/316:25 amKIN - PWM
2 stops16h 26mAmerican Airlines
Deal found 12/10$666
This United Airlines deal was found by Cheapflights users on 12/10. 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 12/116:00 amPWM - KIN
3 stops32h 02mUnited Airlines
Wed 12/313:02 pmKIN - PWM
2 stops32h 57mUnited Airlines
Deal found 12/10$744
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/206:00 amPWM - KIN
2 stops17h 10mAmerican Airlines
Tue 12/306:00 pmKIN - PWM
2 stops18h 10mAmerican Airlines
Deal found 12/11$777
This Delta deal was found by Cheapflights users on 12/11. 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 12/205:45 amPWM - KIN
1 stop14h 11mDelta
Tue 12/309:00 amKIN - PWM
1 stop13h 43mDelta
Deal found 12/11$1,201
This American Airlines deal was found by Cheapflights users on 12/10. 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.
Wed 12/245:20 pmPWM - KIN
2 stops21h 28mAmerican Airlines
Sun 1/46:00 pmKIN - PWM
2 stops18h 11mAmerican Airlines
Deal found 12/10$1,482

Find flight deals from Portland to Jamaica

Keep the following information in mind while searching for Portland to Jamaica flight deals. Data was last updated December 12, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$331
(United Airlines)

One-way from

$142
(American Airlines)

Popular in

April

Cheapest in

March

Average price

$581
Provider with most accurate pricing for Boston Logan Intl-Montego Bay Sangster Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Montego Bay Sangster Intl flights.
Search Deals
From Portland to Jamaica
Search Deals
One-way flight from Portland to Jamaica
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Jamaica 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 12, 2025.
Use the filters below to find and compare flights from Portland to Jamaica that are best for you.

Fly from

Portland

Fly to

Jamaica

Route

Depart

Return

Price

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Wed 3/18

6:00 am-1:37 pm

1 stop8h 37m

Montego Bay Sangster Intl

Wed 3/25

2:55 pm-10:51 pm

1 stop6h 56m

$331

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Fri 1/2

6:41 pm-12:06 pm

1 stop17h 25m

Montego Bay Sangster Intl

Thu 1/8

4:16 pm-12:06 pm

2 stops19h 50m

$336

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Sun 1/25

5:07 pm-12:58 pm

2 stops19h 51m

Montego Bay Sangster Intl

Sun 2/1

1:58 pm-12:05 pm

2 stops22h 07m

$341

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Wed 12/24

5:45 am-8:41 pm

1 stop14h 56m

Montego Bay Sangster Intl

Wed 12/31

8:00 am-10:43 pm

1 stop14h 43m

$355

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Sat 4/25

1:15 pm-1:15 pm

1 stop25h 00m

Montego Bay Sangster Intl

Sat 5/2

4:35 pm-12:00 pm

2 stops18h 25m

$386

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Sun 1/4

7:17 am-2:14 pm

1 stop6h 57m

Montego Bay Sangster Intl

Sun 1/11

1:58 pm-12:05 pm

2 stops22h 07m

$426

PortlandKingston

PWM - KIN

PWMKIN

Portland

Fri 3/20

6:25 am-8:00 pm

2 stops14h 35m

Kingston Norman Manley

Sun 3/29

9:00 am-12:10 am

2 stops14h 10m

$698

PortlandKingston

PWM - KIN

PWMKIN

Portland

Mon 2/2

7:27 pm-1:45 pm

2 stops42h 18m

Kingston Norman Manley

Thu 2/5

2:55 pm-9:01 am

2 stops42h 06m

$1,285

PortlandKingston

PWM - KIN

PWMKIN

Portland

Wed 12/24

5:20 pm-2:48 pm

2 stops21h 28m

Kingston Norman Manley

Sun 1/4

6:00 pm-12:11 pm

2 stops18h 11m

$1,482

PortlandKingston

PWM - KIN

PWMKIN

Portland

Wed 12/24

5:45 am-7:56 pm

1 stop14h 11m

Kingston Norman Manley

Sun 1/4

9:00 am-10:43 pm

1 stop13h 43m

$1,686

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 14 results
1
2

Best time to book a flight from Portland to Jamaica

Have a flexible travel schedule? Discover the best time to fly to Jamaica 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.

Cheapflights Insights

Everything you need to know about your flight from Portland to Jamaica

What is the cheapest month to book a flight from Portland, Maine to Jamaica?

Currently, March is the cheapest month in which you can book a flight from Portland, Maine to Jamaica (average of $195). Flying from Portland, Maine to Jamaica in August is currently the most expensive (average of $376). 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 JM?

Find hourly flight availability from Portland to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 12, 2025.

It’s optimal to fly from Portland, Maine to Jamaica in the evening. By choosing this option you can save up to 58% on the cost of your flight, compared to a flight in the morning.

Reviews of airlines servicing Jamaica

Get insights into the airlines that provide service to Jamaica. 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 Jamaica. Reviews last updated December 12, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Portland to Jamaica 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
7.9
Good
4,253 reviews

Comfort

8.0

Crew

8.6

Overall

7.9

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,253 reviews
Southwest
7.9
Good
4,253 reviews

Comfort

8.0

Crew

8.6

Overall

7.9

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,008 reviews
Southwest
7.9
Good
4,253 reviews

Comfort

8.0

Crew

8.6

Overall

7.9

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,095 reviews
Southwest
7.9
Good
4,253 reviews

Comfort

8.0

Crew

8.6

Overall

7.9

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,050 reviews
Southwest
7.9
Good
4,253 reviews

Comfort

8.0

Crew

8.6

Overall

7.9

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Portland to Jamaica. 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 Jamaica?

    For a flight from Portland to Jamaica, you will be flying from Portland. Portland (PWM) is just 2.9 mi from the center of the city.

  • How long is the flight from Portland, Maine to Jamaica?

    There are many flights that can get you from Portland, Maine to Jamaica in 8h 37m. Fly via United Airlines, American Airlines, or Delta to get the fastest option. Portland, Maine and Jamaica are separated by a distance of 1791 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    The cheapest airlines for a one-way flight from Portland, Maine to Jamaica are Delta ($314), American Airlines ($322), and United Airlines ($410).

  • Can I find deals for flights from Portland to Jamaica that include hotel bookings?

    Yes. In addition to deals on Portland to Jamaica flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Jamaica?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Jamaica.

  • Can I find deals for business class flights from Portland to Jamaica?

    Yes. Cheapflights offers flight deals from Portland to Jamaica 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 Jamaica?

    Currently, March is the cheapest month in which you can book a flight from Portland, Maine to Jamaica (average of $195). Flying from Portland, Maine to Jamaica in August is currently the most expensive (average of $376). 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 Jamaica

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Portland to Jamaica

Discover the top 4 airlines that operate flights from Portland to Jamaica. 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 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$404Average$516FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$406Average$686FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$423Average$679FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$491Average$681FlexibilityNo cancel feeOn-time63%

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