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Jamaica

$175+ 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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MBJ
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Cheap flight deals from Portland to Jamaica

Keep the following information in mind while searching for Portland to Jamaica flight deals. Data was last updated October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$375
(Delta)

One-way from

$175
(American Airlines)

Popular in

April

Cheapest in

January

Average price

$523
Provider with most accurate pricing for Portland-Montego Bay Sangster Intl flight deals.
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Provider most trusted by Cheapflights users for Portland-Montego Bay Sangster Intl flights.
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From Portland to Jamaica
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One-way flight from Portland to Jamaica
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Highest demand for flights based on searches. 16% potential increase in price ($122 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($55 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 October 29, 2025.

This United Airlines deal was found by Cheapflights users on 10/28. 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 11/106:00 amPWM - MBJ
1 stop8h 29mUnited Airlines
Mon 11/172:48 pmMBJ - PWM
2 stops19h 16mUnited Airlines
Deal found 10/28$384
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/106:00 amPWM - MBJ
1 stop8h 53mAmerican Airlines
Mon 11/171:50 pmMBJ - PWM
1 stop9h 04mAmerican Airlines
Deal found 10/28$428
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/76:37 pmPWM - MBJ
2 stops18h 02mAmerican Airlines
Tue 11/113:50 pmMBJ - PWM
2 stops19h 56mAmerican Airlines
Deal found 10/28$444
This American Airlines deal was found by Cheapflights users on 10/28. 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 12/126:40 pmPWM - MBJ
2 stops18h 20mAmerican Airlines
Fri 12/193:14 pmMBJ - PWM
1 stop7h 37mAmerican Airlines
Deal found 10/28$464
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Sat 12/134:25 pmPWM - MBJ
2 stops21h 40mUnited Airlines
Sat 12/203:55 pmMBJ - PWM
1 stop7h 27mUnited Airlines
Deal found 10/29$476
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Fri 11/77:22 pmPWM - MBJ
1 stop20h 50mUnited Airlines
Tue 11/112:48 pmMBJ - PWM
1 stop23h 24mUnited Airlines
Deal found 10/29$524
This American Airlines deal was found by Cheapflights users on 10/28. 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 12/126:40 pmPWM - KIN
2 stops19h 26mAmerican Airlines
Fri 12/196:25 amKIN - PWM
2 stops16h 26mAmerican Airlines
Deal found 10/28$546
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/76:37 pmPWM - KIN
2 stops19h 39mAmerican Airlines
Mon 11/107:30 amKIN - PWM
2 stops16h 29mAmerican Airlines
Deal found 10/28$652
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/186:00 amPWM - MBJ
1 stop8h 37mUnited Airlines
Thu 12/255:14 pmMBJ - PWM
1 stop16h 30mUnited Airlines
Deal found 10/28$679
This Delta deal was found by Cheapflights users on 10/28. 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 11/31:27 pmPWM - KIN
1 stop7h 33mDelta
Mon 11/109:00 amKIN - PWM
2 stops14h 54mDelta
Deal found 10/28$697
This Delta deal was found by Cheapflights users on 10/28. 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 12/126:08 amPWM - KIN
1 stop13h 58mDelta
Fri 12/199:00 amKIN - PWM
1 stop13h 23mDelta
Deal found 10/28$853
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/35:43 amPWM - KIN
2 stops8h 33mAmerican Airlines
Mon 11/107:30 amKIN - PWM
3 stops14h 05mAmerican Airlines
Deal found 10/28$2,393

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 October 29, 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

Mon 2/9

5:30 am-3:20 pm

1 stop9h 50m

Montego Bay Sangster Intl

Fri 2/13

8:00 am-9:59 pm

1 stop13h 59m

$375

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Mon 11/10

6:00 am-2:29 pm

1 stop8h 29m

Montego Bay Sangster Intl

Mon 11/17

2:48 pm-10:04 am

2 stops19h 16m

$384

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Sun 1/4

5:20 pm-10:21 am

2 stops17h 01m

Montego Bay Sangster Intl

Sun 1/11

4:16 pm-12:06 pm

2 stops19h 50m

$385

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Mon 2/9

5:30 am-3:20 pm

1 stop9h 50m

Montego Bay Sangster Intl

Thu 2/12

12:35 pm-1:51 pm

2 stops25h 16m

$415

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Mon 2/9

5:20 am-3:04 pm

2 stops9h 44m

Montego Bay Sangster Intl

Thu 2/12

11:07 am-11:49 pm

2 stops12h 42m

$443

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Mon 2/9

5:20 am-3:04 pm

2 stops9h 44m

Montego Bay Sangster Intl

Fri 2/13

11:07 am-12:05 pm

2 stops24h 58m

$443

PortlandKingston

PWM - KIN

PWMKIN

Portland

Tue 2/24

6:00 am-8:00 pm

2 stops14h 00m

Kingston Norman Manley

Thu 2/26

9:00 am-9:59 pm

1 stop12h 59m

$454

PortlandKingston

PWM - KIN

PWMKIN

Portland

Tue 2/24

7:00 am-8:44 pm

2 stops13h 44m

Kingston Norman Manley

Thu 2/26

11:09 am-12:12 pm

2 stops25h 03m

$528

PortlandKingston

PWM - KIN

PWMKIN

Portland

Fri 12/12

6:40 pm-2:06 pm

2 stops19h 26m

Kingston Norman Manley

Fri 12/19

6:25 am-10:51 pm

2 stops16h 26m

$546

PortlandKingston

PWM - KIN

PWMKIN

Portland

Fri 12/12

6:08 am-8:06 pm

1 stop13h 58m

Kingston Norman Manley

Fri 12/19

9:00 am-10:23 pm

1 stop13h 23m

$853

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 20 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 October 29, 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 October 29, 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
8.0
Very good
4,241 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,992 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,999 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,032 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,907 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 29m. Fly via Delta, United Airlines, or American Airlines 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.

  • 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 5 airlines flying from Portland to Jamaica

Discover the top 5 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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$404Average$516FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$406Average$703FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$414Average$741FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$419Average$677FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$491Average$685FlexibilityNo cancel feeOn-time63%

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