HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Jamaica

$177+ 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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MBJ
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Jamaica with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 septiembre 11, 2025.

Round-trip from

$389
(American Airlines)

One-way from

$177
(American Airlines)

Popular in

April

Cheapest in

January

Average price

$496
From Portland to Jamaica
Search Deals
One-way flight from Portland to Jamaica
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($96 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($52 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 septiembre 11, 2025.

This American Airlines deal was found by Cheapflights users on 9/10. 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.
lun. 12/157:02 amPWM - MBJ
1 stop8h 47mAmerican Airlines
lun. 12/223:14 pmMBJ - PWM
1 stop7h 34mAmerican Airlines
Deal found 9/10$389
This American Airlines deal was found by Cheapflights users on 9/10. 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.
vie. 10/246:14 amPWM - MBJ
1 stop7h 31mAmerican Airlines
vie. 10/313:20 pmMBJ - PWM
2 stops19h 06mAmerican Airlines
Deal found 9/10$393
This American Airlines deal was found by Cheapflights users on 9/10. 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.
mar. 12/96:38 pmPWM - KIN
2 stops19h 28mAmerican Airlines
sáb. 12/206:25 amKIN - PWM
2 stops16h 23mAmerican Airlines
Deal found 9/10$442
This American Airlines deal was found by Cheapflights users on 9/10. 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.
vie. 11/76:37 pmPWM - MBJ
2 stops19h 35mAmerican Airlines
mar. 11/114:28 pmMBJ - PWM
2 stops19h 40mAmerican Airlines
Deal found 9/10$492
This American Airlines deal was found by Cheapflights users on 9/9. 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.
mié. 12/247:17 amPWM - MBJ
2 stops26h 50mAmerican Airlines
mié. 12/316:05 pmMBJ - PWM
2 stops18h 06mAmerican Airlines
Deal found 9/9$545
This American Airlines deal was found by Cheapflights users on 9/10. 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.
jue. 12/186:40 pmPWM - MBJ
2 stops18h 38mAmerican Airlines
jue. 12/253:52 pmMBJ - PWM
1 stop7h 03mAmerican Airlines
Deal found 9/10$590

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 septiembre 11, 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

lun. 2/9

5:30 am-3:15 pm

1 stop9h 45m

Montego Bay Sangster Intl

vie. 2/13

2:15 pm-11:49 pm

1 stop9h 34m

$389

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

vie. 10/24

6:14 am-12:45 pm

1 stop7h 31m

Montego Bay Sangster Intl

vie. 10/31

3:20 pm-11:26 am

2 stops19h 06m

$393

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

lun. 12/15

5:46 am-3:49 pm

2 stops10h 03m

Montego Bay Sangster Intl

lun. 12/22

11:27 am-11:45 pm

2 stops12h 18m

$435

PortlandKingston

PWM - KIN

PWMKIN

Portland

mar. 12/9

6:38 pm-2:06 pm

2 stops19h 28m

Kingston Norman Manley

sáb. 12/20

6:25 am-10:48 pm

2 stops16h 23m

$442

PortlandKingston

PWM - KIN

PWMKIN

Portland

mar. 2/24

6:00 am-8:00 pm

2 stops14h 00m

Kingston Norman Manley

jue. 2/26

9:00 am-9:59 pm

1 stop12h 59m

$453

PortlandKingston

PWM - KIN

PWMKIN

Portland

lun. 2/2

4:50 pm-11:55 am

2 stops19h 05m

Kingston Norman Manley

vie. 2/6

8:25 am-10:31 pm

2 stops14h 06m

$453

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

vie. 11/7

5:37 pm-3:28 pm

1 stop21h 51m

Montego Bay Sangster Intl

mar. 11/11

4:28 pm-12:08 pm

2 stops19h 40m

$501

PortlandKingston

PWM - KIN

PWMKIN

Portland

mar. 2/24

2:29 pm-11:45 am

2 stops21h 16m

Kingston Norman Manley

jue. 2/26

1:50 pm-12:09 pm

2 stops22h 19m

$527

PortlandKingston

PWM - KIN

PWMKIN

Portland

lun. 2/2

5:30 am-8:00 pm

1 stop14h 30m

Kingston Norman Manley

vie. 2/6

9:00 am-9:59 pm

1 stop12h 59m

$638

PortlandKingston

PWM - KIN

PWMKIN

Portland

dom. 2/8

4:50 pm-11:55 am

2 stops19h 05m

Kingston Norman Manley

sáb. 2/21

3:50 pm-11:39 am

2 stops19h 49m

$850

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 17 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, January is the cheapest month in which you can book a flight from Portland, Maine to Jamaica (average of $403). Flying from Portland, Maine to Jamaica in July is currently the most expensive (average of $560). 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 septiembre 11, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Portland, Maine to Jamaica as you normally would.

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 septiembre 11, 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
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
2,913 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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 7h 31m. Fly via Delta 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, January is the cheapest month in which you can book a flight from Portland, Maine to Jamaica (average of $403). Flying from Portland, Maine to Jamaica in July is currently the most expensive (average of $560). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Jamaica

See prices for flight routes from nearby airports that may be better suited for you.
Boston to Luis Munoz Marin Intl flights
Boston to Oranjestad flights
Boston to Punta Cana flights
Boston to Santo Domingo flights
Boston to Montego Bay flights
Boston to Saint Thomas Island flights
Boston to Santiago de los Caballeros flights
Boston to Nassau flights
Boston to Simpson Bay flights
Boston to Providenciales flights
Boston to Bridgetown flights
Boston to George Town flights
Boston to Castries flights
Boston to Christiansted flights
Boston to Kingston flights
Boston to Willemstad flights
Boston to St. John's flights
Boston to Road Town flights
Portland to Luis Munoz Marin Intl flights
Boston to Aguadilla flights
Boston to St. George's flights
Boston to Puerto Plata flights
Boston to Basseterre flights
Boston to Port of Spain flights
Boston to Freeport flights
Boston to Ponce flights
Portland to Saint Thomas Island flights
Boston to Castries flights
Bangor to Luis Munoz Marin Intl flights
Portland to Punta Cana flights
Boston to Kralendijk flights
Portland to Oranjestad flights
Boston to Marsh Harbour flights
Boston to Gregory Town flights
Portland to Nassau flights
Portland to George Town flights
Boston to Fort-de-France flights
Boston to Georgetown flights
Boston to Kingstown flights
Portland to Montego Bay flights
Boston to The Valley flights
Boston to Vieques flights
Portland to Simpson Bay flights
Boston to Roseau flights
Boston to Gustavia flights
Portland to Providenciales flights
Boston to Cap Haitien flights
Portland to Castries flights
Boston to Mayagüez flights
Boston to Pointe-à-Pitre flights

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 septiembre 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$404Average$504FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$406Average$686FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$414Average$741FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$419Average$667FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$491Average$761FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.