$178+ Cheap flights from Portland, ME (PWM) to Jamaica
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MBJ
Oct 6 — Oct 131
Round-trip
1 adult, Economy
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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
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Cheapest flights from Portland to JamaicaExplore 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 September 6, 2026.
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 September 6, 2026.
This United Airlines deal was found by Cheapflights users on 9/1. 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 12/57:55 pm -
2 stops17h 53m
Tue 12/151:25 pm -
1 stop9h 59m
Deal found 9/1![United Airlines logo]()
$404
This American Airlines deal was found by Cheapflights users on 9/1. 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 10/97:26 pm -
2 stops18h 28m
Sat 10/175:13 pm -
2 stops16h 50m
Deal found 9/1![American Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 9/2. 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 12/106:47 pm -
2 stops17h 15m
Sun 12/136:09 pm -
2 stops16h 28m
Deal found 9/2![American Airlines logo]()
$414
This American Airlines deal was found by Cheapflights users on 9/1. 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 11/76:47 pm -
1 stop18h 25m
Sat 11/146:09 pm -
2 stops16h 28m
Deal found 9/1![American Airlines logo]()
$415
This United Airlines deal was found by Cheapflights users on 9/5. 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 12/37:55 pm -
1 stop18h 19m
Tue 12/81:25 pm -
1 stop7h 17m
Deal found 9/5![United Airlines logo]()
$431
This United Airlines deal was found by Cheapflights users on 9/1. 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 11/76:00 am -
1 stop8h 14m
Sat 11/146:00 pm -
1 stop15h 00m
Deal found 9/1![United Airlines logo]()
$455
This American Airlines deal was found by Cheapflights users on 9/2. 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 11/286:47 pm -
1 stop17h 58m
Sat 12/511:59 am -
1 stop10h 58m
Deal found 9/2![American Airlines logo]()
$466
This American Airlines deal was found by Cheapflights users on 9/4. 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.
Wed 11/412:13 pm -
2 stops22h 02m
Mon 11/93:22 pm -
2 stops19h 15m
Deal found 9/4![American Airlines logo]()
$469
This JetBlue deal was found by Cheapflights users on 9/2. 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.
Mon 10/266:30 am -
1 stop7h 18m
Fri 10/3011:45 am -
1 stop10h 58m
Deal found 9/2![JetBlue logo]()
$484
This American Airlines deal was found by Cheapflights users on 9/3. 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.
Mon 10/197:26 pm -
2 stops16h 31m
Wed 10/285:03 pm -
2 stops17h 00m
Deal found 9/3![American Airlines logo]()
$492
This Priceline deal was found by Cheapflights users on 9/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:00 am -
1 stop9h 40m
Wed 10/2812:15 pm -
1 stop10h 28m
Deal found 9/3![JetBlue logo]()
$502
This United Airlines deal was found by Cheapflights users on 9/1. 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 10/265:50 am -
1 stop8h 24m
Fri 10/3012:25 pm -
1 stop9h 56m
Deal found 9/1![United Airlines logo]()
$524
Best flights from Portland to JamaicaDiscover carefully curated flight deals from Portland to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 6, 2026.
Discover carefully curated flight deals from Portland to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 6, 2026.
This United Airlines deal was found by Cheapflights users on 9/1. 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 12/57:55 pm -
2 stops17h 53m
Tue 12/151:25 pm -
1 stop9h 59m
Deal found 9/1![United Airlines logo]()
$404
This Delta deal was found by Cheapflights users on 9/1. 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.
Tue 2/26:00 am -
1 stop9h 25m
Tue 2/92:00 pm -
1 stop9h 49m
Deal found 9/1![Delta logo]()
$405
This American Airlines deal was found by Cheapflights users on 9/1. 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 11/76:47 pm -
1 stop18h 25m
Sat 11/146:09 pm -
2 stops16h 28m
Deal found 9/1![American Airlines logo]()
$415
This Priceline deal was found by Cheapflights users on 9/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:00 am -
1 stop9h 40m
Wed 10/2812:15 pm -
1 stop10h 28m
Deal found 9/3![JetBlue logo]()
$502
This United Airlines deal was found by Cheapflights users on 9/1. 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 11/76:00 am -
1 stop8h 14m
Sat 11/146:00 pm -
1 stop15h 00m
Deal found 9/1![United Airlines logo]()
$455
This JetBlue deal was found by Cheapflights users on 9/5. 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.
Tue 10/206:00 am -
1 stop9h 40m
Fri 10/2312:20 pm -
1 stop10h 34m
Deal found 9/5![JetBlue logo]()
$533
This United Airlines deal was found by Cheapflights users on 9/1. 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 10/265:50 am -
1 stop8h 24m
Fri 10/3012:25 pm -
1 stop9h 56m
Deal found 9/1![United Airlines logo]()
$524
This American Airlines deal was found by Cheapflights users on 9/3. 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 10/105:38 pm -
2 stops18h 19m
Wed 10/1411:57 am -
2 stops11h 02m
Deal found 9/3![American Airlines logo]()
$651
This Delta deal was found by Cheapflights users on 9/3. 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.
Fri 9/256:30 am -
2 stops14h 40m
Tue 9/299:10 am -
2 stops13h 07m
Deal found 9/3![Delta logo]()
$732
This United Airlines deal was found by Cheapflights users on 9/1. 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.
Tue 10/208:03 am -
2 stops30h 52m
Fri 10/232:57 pm -
2 stops22h 41m
Deal found 9/1![United Airlines logo]()
$840
Last-minute flights from Portland to JamaicaDiscover last-minute flight deals from Portland to Jamaica. Data last updated September 6, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Jamaica. Data last updated September 6, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/3. 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.
Fri 9/252:10 pm -
1 stop7h 00m
Tue 9/299:10 am -
1 stop13h 18m
Deal found 9/3![Delta logo]()
$654
This United Airlines deal was found by Cheapflights users on 9/6. 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 9/256:00 am -
2 stops32h 51m
Tue 9/292:57 pm -
2 stops18h 43m
Deal found 9/6![United Airlines logo]()
$789
This American Airlines deal was found by Cheapflights users on 9/1. 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 10/97:26 pm -
2 stops18h 28m
Sat 10/175:13 pm -
2 stops16h 50m
Deal found 9/1![American Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 9/3. 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 10/105:38 pm -
2 stops18h 19m
Wed 10/1411:57 am -
2 stops11h 02m
Deal found 9/3![American Airlines logo]()
$651
This FlightHub deal was found by Cheapflights users on 9/3. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:00 am -
1 stop9h 40m
Wed 10/1412:20 pm -
1 stop10h 34m
Deal found 9/3![JetBlue logo]()
$833
This American Airlines deal was found by Cheapflights users on 9/3. 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.
Mon 10/197:26 pm -
2 stops16h 31m
Wed 10/285:03 pm -
2 stops17h 00m
Deal found 9/3![American Airlines logo]()
$492
This Priceline deal was found by Cheapflights users on 9/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:00 am -
1 stop9h 40m
Wed 10/2812:15 pm -
1 stop10h 28m
Deal found 9/3![JetBlue logo]()
$502
This JetBlue deal was found by Cheapflights users on 9/5. 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.
Tue 10/206:00 am -
1 stop9h 40m
Fri 10/2312:20 pm -
1 stop10h 34m
Deal found 9/5![JetBlue logo]()
$533
This United Airlines deal was found by Cheapflights users on 9/1. 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.
Tue 10/208:03 am -
2 stops30h 52m
Fri 10/232:57 pm -
2 stops22h 41m
Deal found 9/1![United Airlines logo]()
$840
This JetBlue deal was found by Cheapflights users on 9/2. 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.
Mon 10/266:30 am -
1 stop7h 18m
Fri 10/3011:45 am -
1 stop10h 58m
Deal found 9/2![JetBlue logo]()
$484
This United Airlines deal was found by Cheapflights users on 9/1. 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 10/265:50 am -
1 stop8h 24m
Fri 10/3012:25 pm -
1 stop9h 56m
Deal found 9/1![United Airlines logo]()
$524
One-way flights from Portland to JamaicaSearch for one-way flight options from Portland to Jamaica. Find affordable one-way fares based on user searches. Data last updated September 6, 2026.
Search for one-way flight options from Portland to Jamaica. Find affordable one-way fares based on user searches. Data last updated September 6, 2026.
This United Airlines deal was found by Cheapflights users on 9/2. 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 12/57:55 pm -
1 stop16h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![United Airlines logo]()
$178
This American Airlines deal was found by Cheapflights users on 9/1. 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 12/76:47 pm -
2 stops17h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![American Airlines logo]()
$184
This deal was found by Cheapflights users on 9/1. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:00 am -
1 stop9h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![JetBlue logo]()
$237
This American Airlines deal was found by Cheapflights users on 9/2. 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 10/137:26 pm -
2 stops16h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![American Airlines logo]()
$256
This American Airlines deal was found by Cheapflights users on 9/6. 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 10/105:38 pm -
2 stops18h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![American Airlines logo]()
$259
This American Airlines deal was found by Cheapflights users on 9/5. 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 9/306:00 pm -
2 stops19h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![American Airlines logo]()
$264
This United Airlines deal was found by Cheapflights users on 9/2. 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 9/307:25 pm -
2 stops41h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![United Airlines logo]()
$291
This Priceline deal was found by Cheapflights users on 9/2. 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.
Tue 10/136:00 am -
1 stop9h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![JetBlue logo]()
$299
This American Airlines deal was found by Cheapflights users on 9/5. 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 10/315:37 pm -
2 stops22h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![American Airlines logo]()
$300
This Delta deal was found by Cheapflights users on 9/4. 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.
Wed 9/306:02 am -
1 stop6h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Delta logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:09 pm -
3 stops43h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$331
This United Airlines deal was found by Cheapflights users on 9/1. 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 9/116:00 am -
2 stops32h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![United Airlines logo]()
$340
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 September 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $404 (United Airlines) |
One-way from | $178 (United Airlines) |
Popular in | February |
Cheapest in | May |
Average price | $715 |
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 7,457,451 searches. Data last updated September 6, 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
Cheapest round-trip
PortlandMontego Bay
PWM Portland - MBJ Montego Bay Sangster Intl
PWMMBJ
Portland
Sat 12/5
7:55 pm-12:13 pm
1 stop16h 18m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$178
PortlandMontego Bay
PWM Portland - MBJ Montego Bay Sangster Intl
PWMMBJ
Portland
Mon 12/7
7:55 pm-12:13 pm
1 stop16h 18m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$178
PortlandMontego Bay
PWM Portland - MBJ Montego Bay Sangster Intl
PWMMBJ
Portland
Mon 12/7
6:47 pm-12:22 pm
2 stops17h 35m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$184
PortlandKingston
PWM Portland - KIN Kingston Norman Manley
PWMKIN
Portland
Sun 10/18
6:00 am-2:40 pm
1 stop9h 40m
Kingston Norman Manley
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$237
PortlandKingston
PWM Portland - KIN Kingston Norman Manley
PWMKIN
Portland
Tue 10/13
7:26 pm-10:57 am
2 stops16h 31m
Kingston Norman Manley
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$256
PortlandMontego Bay
PWM Portland - MBJ Montego Bay Sangster Intl
PWMMBJ
Portland
Sat 10/10
5:38 pm-11:08 am
2 stops18h 30m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$259
PortlandMontego Bay
PWM Portland - MBJ Montego Bay Sangster Intl
PWMMBJ
Portland
Wed 9/30
6:00 pm-12:53 pm
2 stops19h 53m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$264
PortlandMontego Bay
PWM Portland - MBJ Montego Bay Sangster Intl
PWMMBJ
Portland
Wed 9/30
7:25 pm-11:43 am
2 stops41h 18m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$291
Quickest round-trip
PortlandMontego Bay
PWM Portland - MBJ Montego Bay Sangster Intl
PWMMBJ
Portland
Wed 9/30
6:02 am-11:33 am
1 stop6h 31m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$317
PortlandMontego Bay
PWM Portland - MBJ Montego Bay Sangster Intl
PWMMBJ
Portland
Wed 11/25
5:09 pm-12:56 pm
3 stops43h 47m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$331
Showing 1-10 of 24 resultsSorted by cheapest first
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.
PWM-MBJ
PWM-KIN
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
PWM-JM0
PWM-MBJ
PWM-KIN
What is the cheapest month to book a flight from Portland, Maine to Jamaica?
Currently, May is the cheapest month in which you can book a flight from Portland, Maine to Jamaica (average of $352). Flying from Portland, Maine to Jamaica in February is currently the most expensive (average of $1,008). 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 September 6, 2026.
Peruse reviews from past customers who have flown with United Airlines and American 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.
Food
6.6
Overall
7.4
Comfort
7.3
Crew
8.1
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Food
6.6
Overall
7.4
Comfort
7.3
Crew
8.1
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Food
6.6
Overall
7.4
Comfort
7.3
Crew
8.1
Entertainment
7.1
Boarding
7.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Related info for your journey
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Top 2 airlines flying from Portland to Jamaica
Discover the top 2 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 7,457,451 searches. Data last updated September 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$332 | Average$675 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$352 | Average$636 | FlexibilityNo cancel fee | On-time71% |