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Jamaica

$163+ 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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MBJ
Apr 22 — Apr 291
Wed 4/22
Wed 4/29
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 March 23, 2026.

This American Airlines deal was found by Cheapflights users on 3/22. 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 5/177:10 am
PWM
-
MBJ
1 stop7h 15m
American Airlines
Sat 5/232:30 pm
MBJ
-
PWM
1 stop9h 05m
American Airlines
Deal found 3/22$352
This American Airlines deal was found by Cheapflights users on 3/21. 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.
Wed 5/67:10 am
PWM
-
MBJ
1 stop7h 15m
American Airlines
Wed 5/132:29 pm
MBJ
-
PWM
2 stops18h 38m
American Airlines
Deal found 3/21$362
This American Airlines deal was found by Cheapflights users on 3/20. 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 11/276:39 pm
PWM
-
MBJ
2 stops15h 36m
American Airlines
Fri 12/42:02 pm
MBJ
-
PWM
2 stops9h 35m
American Airlines
Deal found 3/20$391
This American Airlines deal was found by Cheapflights users on 3/23. 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.
Sat 5/235:57 pm
PWM
-
MBJ
2 stops18h 48m
American Airlines
Mon 6/12:08 pm
MBJ
-
PWM
2 stops19h 24m
American Airlines
Deal found 3/23$407
This American Airlines deal was found by Cheapflights users on 3/21. 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.
Tue 4/286:00 am
PWM
-
MBJ
1 stop9h 15m
American Airlines
Thu 4/303:20 pm
MBJ
-
PWM
1 stop7h 07m
American Airlines
Deal found 3/21$426
This American Airlines deal was found by Cheapflights users on 3/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:57 pm
PWM
-
MBJ
1 stop16h 28m
American Airlines
Sat 8/223:20 pm
MBJ
-
PWM
2 stops18h 52m
American Airlines
Deal found 3/18$431
This Southwest deal was found by Cheapflights users on 3/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:40 am
PWM
-
MBJ
1 stop8h 50m
Southwest
Sat 5/92:45 pm
MBJ
-
PWM
1 stop7h 25m
Southwest
Deal found 3/18$446
This Delta deal was found by Cheapflights users on 3/21. 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.
Fri 11/276:00 am
PWM
-
MBJ
1 stop10h 35m
Delta
Fri 12/41:50 pm
MBJ
-
PWM
1 stop9h 59m
Delta
Deal found 3/21$453
This KAYAK deal was found by Cheapflights users on 3/18. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/262:19 pm
PWM
-
KIN
1 stop9h 26m
JetBlue
Tue 6/211:59 pm
KIN
-
PWM
1 stop12h 25m
JetBlue
Deal found 3/18$460
This KAYAK deal was found by Cheapflights users on 3/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/232:19 pm
PWM
-
KIN
1 stop9h 26m
JetBlue
Mon 6/111:59 pm
KIN
-
PWM
1 stop12h 25m
JetBlue
Deal found 3/20$485
This Priceline deal was found by Cheapflights users on 3/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:00 am
PWM
-
KIN
1 stop11h 53m
JetBlue
Wed 5/132:36 pm
KIN
-
PWM
1 stop8h 00m
JetBlue
Deal found 3/21$487
This American Airlines deal was found by Cheapflights users on 3/20. 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.
Tue 5/265:57 pm
PWM
-
KIN
2 stops18h 44m
American Airlines
Tue 6/28:00 am
KIN
-
PWM
2 stops13h 41m
American Airlines
Deal found 3/20$491

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 March 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$352
(American Airlines)

One-way from

$163
(American Airlines)

Popular in

April

Cheapest in

May

Average price

$517
Provider with most accurate pricing for Portland-Montego Bay Sangster Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-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. 11% potential increase in price ($82 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($58 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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 March 23, 2026.
Use the filters below to find and compare flights from Portland to Jamaica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Sun 5/17

7:23 pm-11:51 am

2 stops17h 28m

Montego Bay Sangster Intl

Sat 5/23

2:30 pm-12:35 am

1 stop9h 05m

$357

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Wed 5/6

7:10 am-1:25 pm

1 stop7h 15m

Montego Bay Sangster Intl

Wed 5/13

2:29 pm-10:07 am

2 stops18h 38m

$362

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Sat 8/15

6:50 pm-1:30 pm

2 stops19h 40m

Montego Bay Sangster Intl

Sat 8/22

3:20 pm-11:12 am

2 stops18h 52m

$391

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Sat 5/23

5:57 pm-11:45 am

2 stops18h 48m

Montego Bay Sangster Intl

Mon 6/1

2:08 pm-10:32 am

2 stops19h 24m

$407
Quickest round-trip

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Sat 5/2

5:40 am-1:30 pm

1 stop8h 50m

Montego Bay Sangster Intl

Sat 5/9

2:45 pm-11:10 pm

1 stop7h 25m

$446

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Tue 4/28

7:33 pm-3:10 pm

1 stop20h 37m

Montego Bay Sangster Intl

Thu 4/30

4:12 pm-10:23 am

2 stops17h 11m

$474

PortlandKingston

PWM - KIN

PWMKIN

Portland

Wed 5/6

6:00 am-4:53 pm

1 stop11h 53m

Kingston Norman Manley

Wed 5/13

2:36 pm-11:36 pm

1 stop8h 00m

$487

PortlandKingston

PWM - KIN

PWMKIN

Portland

Tue 5/26

6:54 pm-11:41 am

2 stops17h 47m

Kingston Norman Manley

Tue 6/2

8:00 am-10:41 pm

2 stops13h 41m

$491

PortlandKingston

PWM - KIN

PWMKIN

Portland

Sat 5/23

2:19 pm-10:45 pm

1 stop9h 26m

Kingston Norman Manley

Mon 6/1

11:59 pm-1:24 pm

1 stop12h 25m

$510

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Sat 5/23

6:00 am-1:03 pm

1 stop8h 03m

Montego Bay Sangster Intl

Mon 6/1

2:24 pm-11:58 pm

1 stop8h 34m

$512

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/20

Showing 1-10 of 20 resultsSorted by cheapest first
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 $200). Flying from Portland, Maine to Jamaica in August is currently the most expensive (average of $366). 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.

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 March 23, 2026.
Peruse reviews from past customers who have flown with Delta,United Airlines, andAmerican 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.
Delta
7.9
Good
8,319 reviews

Food

7.2

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,319 reviews
Delta
7.9
Good
8,319 reviews

Food

7.2

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,460 reviews
Delta
7.9
Good
8,319 reviews

Food

7.2

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.1
Good
11,489 reviews
Delta
7.9
Good
8,319 reviews

Food

7.2

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 7h 15m. Fly via American Airlines or JetBlue 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 ($278), 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 $200). Flying from Portland, Maine to Jamaica in August is currently the most expensive (average of $366). 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

Browse thousands of different options on Cheapflights for your next trip

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Top 3 airlines flying from Portland to Jamaica

Discover the top 3 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 March 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$232Average$529FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$246Average$675FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$426Average$623FlexibilityNo cancel feeOn-time71%

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