$177+ 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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MBJ
Nov 23 — Nov 301
Round-trip
1 adult, Economy
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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 October 24, 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 October 24, 2026.
This United Airlines deal was found by Cheapflights users on 10/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:55 pm -
2 stops18h 44m
Fri 12/111:25 pm -
1 stop7h 17m
Deal found 10/20![United Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 10/24. 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 12/76:44 pm -
2 stops17h 40m
Mon 12/146:09 pm -
2 stops16h 21m
Deal found 10/24![American Airlines logo]()
$428
This American Airlines deal was found by Cheapflights users on 10/20. 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 12/46:44 pm -
1 stop16h 29m
Fri 12/112:26 pm -
1 stop20h 04m
Deal found 10/20![American Airlines logo]()
$449
This United Airlines deal was found by Cheapflights users on 10/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/79:46 am -
1 stop6h 33m
Sat 11/145:21 pm -
1 stop16h 46m
Deal found 10/21![United Airlines logo]()
$455
This United Airlines deal was found by Cheapflights users on 10/24. 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 12/87:55 pm -
1 stop16h 18m
Tue 12/153:20 pm -
1 stop8h 04m
Deal found 10/24![United Airlines logo]()
$481
This American Airlines deal was found by Cheapflights users on 10/23. 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.
Thu 12/36:44 pm -
2 stops17h 40m
Mon 12/71:24 pm -
2 stops21h 06m
Deal found 10/23![American Airlines logo]()
$492
This American Airlines deal was found by Cheapflights users on 10/22. 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.
Thu 12/36:44 pm -
2 stops17h 40m
Tue 12/82:26 pm -
1 stop8h 53m
Deal found 10/22![American Airlines logo]()
$509
This American Airlines deal was found by Cheapflights users on 10/22. 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.
Thu 11/196:47 pm -
2 stops20h 31m
Sun 11/224:21 pm -
2 stops18h 17m
Deal found 10/22![American Airlines logo]()
$724
This United Airlines deal was found by Cheapflights users on 10/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/165:35 am -
2 stops32h 17m
Thu 11/192:58 pm -
2 stops32h 23m
Deal found 10/20![United Airlines logo]()
$727
This American Airlines deal was found by Cheapflights users on 10/21. 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.
Sun 12/66:44 pm -
2 stops17h 53m
Sun 12/131:42 pm -
2 stops20h 48m
Deal found 10/21![American Airlines logo]()
$782
This American Airlines deal was found by Cheapflights users on 10/20. 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.
Sat 12/56:00 am -
2 stops9h 26m
Sat 12/196:35 am -
2 stops16h 24m
Deal found 10/20![American Airlines logo]()
$869
This United Airlines deal was found by Cheapflights users on 10/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/66:00 am -
2 stops31h 50m
Sun 12/133:03 pm -
3 stops22h 35m
Deal found 10/21![United Airlines logo]()
$1,101
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 October 24, 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 October 24, 2026.
This United Airlines deal was found by Cheapflights users on 10/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:55 pm -
2 stops18h 44m
Fri 12/111:25 pm -
1 stop7h 17m
Deal found 10/20![United Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 10/23. 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.
Thu 12/36:44 pm -
2 stops17h 40m
Mon 12/71:24 pm -
2 stops21h 06m
Deal found 10/23![American Airlines logo]()
$492
This United Airlines deal was found by Cheapflights users on 10/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/79:46 am -
1 stop6h 33m
Sat 11/145:21 pm -
1 stop16h 46m
Deal found 10/21![United Airlines logo]()
$455
This United Airlines deal was found by Cheapflights users on 10/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/116:00 am -
1 stop8h 14m
Mon 1/251:25 pm -
1 stop10h 07m
Deal found 10/23![United Airlines logo]()
$482
This United Airlines deal was found by Cheapflights users on 10/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/77:00 am -
1 stop7h 14m
Mon 12/143:20 pm -
1 stop17h 45m
Deal found 10/23![United Airlines logo]()
$512
This United Airlines deal was found by Cheapflights users on 10/19. 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 -
2 stops44h 24m
Tue 12/81:25 pm -
1 stop7h 17m
Deal found 10/19![United Airlines logo]()
$536
This American Airlines deal was found by Cheapflights users on 10/21. 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.
Sun 12/66:44 pm -
2 stops17h 53m
Sun 12/131:42 pm -
2 stops20h 48m
Deal found 10/21![American Airlines logo]()
$782
This United Airlines deal was found by Cheapflights users on 10/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/167:10 am -
1 stop7h 04m
Sat 1/305:21 pm -
1 stop21h 00m
Deal found 10/23![United Airlines logo]()
$550
This United Airlines deal was found by Cheapflights users on 10/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/17:30 am -
2 stops30h 18m
Fri 2/53:20 pm -
2 stops23h 31m
Deal found 10/20![United Airlines logo]()
$560
This United Airlines deal was found by Cheapflights users on 10/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/165:35 am -
2 stops32h 17m
Thu 11/192:58 pm -
2 stops32h 23m
Deal found 10/20![United Airlines logo]()
$727
This United Airlines deal was found by Cheapflights users on 10/24. 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 12/89:12 am -
2 stops28h 38m
Tue 12/153:03 pm -
2 stops23h 34m
Deal found 10/24![United Airlines logo]()
$747
This United Airlines deal was found by Cheapflights users on 10/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/66:00 am -
2 stops31h 50m
Sun 12/133:03 pm -
3 stops22h 35m
Deal found 10/21![United Airlines logo]()
$1,101
Last-minute flights from Portland to JamaicaDiscover last-minute flight deals from Portland to Jamaica. Data last updated October 24, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Jamaica. Data last updated October 24, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:00 am -
2 stops10h 19m
Sat 11/145:21 pm -
1 stop16h 46m
Deal found 10/21![United Airlines logo]()
$455
This United Airlines deal was found by Cheapflights users on 10/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/165:35 am -
2 stops32h 17m
Thu 11/192:58 pm -
2 stops32h 23m
Deal found 10/20![United Airlines logo]()
$727
This United Airlines deal was found by Cheapflights users on 10/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/189:46 am -
2 stops28h 28m
Wed 11/251:25 pm -
2 stops25h 01m
Deal found 10/22![United Airlines logo]()
$586
This American Airlines deal was found by Cheapflights users on 10/22. 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.
Thu 11/196:47 pm -
2 stops20h 31m
Sun 11/224:21 pm -
2 stops18h 17m
Deal found 10/22![American Airlines logo]()
$724
This United Airlines deal was found by Cheapflights users on 10/24. 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 11/195:50 am -
2 stops32h 02m
Sun 11/222:58 pm -
3 stops56h 23m
Deal found 10/24![United Airlines logo]()
$1,120
This United Airlines deal was found by Cheapflights users on 10/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/225:50 am -
1 stop8h 24m
Wed 11/251:25 pm -
2 stops25h 01m
Deal found 10/22![United Airlines logo]()
$639
This United Airlines deal was found by Cheapflights users on 10/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/245:50 am -
1 stop8h 24m
Mon 12/71:25 pm -
1 stop7h 17m
Deal found 10/22![United Airlines logo]()
$567
This United Airlines deal was found by Cheapflights users on 10/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:50 am -
1 stop8h 24m
Mon 12/71:25 pm -
1 stop7h 17m
Deal found 10/22![United Airlines logo]()
$577
This American Airlines deal was found by Cheapflights users on 10/20. 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.
Sat 11/286:47 pm -
2 stops17h 30m
Sat 12/51:33 pm -
2 stops20h 57m
Deal found 10/20![American Airlines logo]()
$518
This Delta deal was found by Cheapflights users on 10/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/286:00 am -
1 stop10h 57m
Sat 12/51:55 pm -
1 stop10h 26m
Deal found 10/20![Delta logo]()
$564
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 October 24, 2026.
Search for one-way flight options from Portland to Jamaica. Find affordable one-way fares based on user searches. Data last updated October 24, 2026.
This United Airlines deal was found by Cheapflights users on 10/24. 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 11/105:50 am -
1 stop8h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![United Airlines logo]()
$177
This Delta deal was found by Cheapflights users on 10/21. 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.
Mon 11/26:01 am -
1 stop10h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Delta logo]()
$198
This American Airlines deal was found by Cheapflights users on 10/21. 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.
Fri 10/304:40 pm -
2 stops19h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$204
This American Airlines deal was found by Cheapflights users on 10/23. 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 11/143:04 pm -
2 stops19h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![American Airlines logo]()
$205
This Southwest deal was found by Cheapflights users on 10/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/15:20 am -
1 stop9h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Southwest logo]()
$208
This American Airlines deal was found by Cheapflights users on 10/21. 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.
Mon 11/26:47 pm -
1 stop18h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$211
This American Airlines deal was found by Cheapflights users on 10/24. 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 11/66:47 pm -
2 stops17h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![American Airlines logo]()
$214
This deal was found by Cheapflights users on 10/23. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/77:00 am -
1 stop7h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![United Airlines logo]()
$227
This American Airlines deal was found by Cheapflights users on 10/21. 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.
Thu 10/297:26 pm -
2 stops16h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$259
This United Airlines deal was found by Cheapflights users on 10/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:30 pm -
1 stop20h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![United Airlines logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/145:09 pm -
3 stops22h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/15:00 pm -
3 stops43h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Breeze Airways logo]()
$306
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 October 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $378 (American Airlines) |
One-way from | $177 (United Airlines) |
Popular in | February |
Cheapest in | May |
Average price | $635 |
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 October 24, 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
Tue 11/10
5:50 am-2:14 pm
1 stop8h 24m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$177
PortlandMontego Bay
PWM Portland - MBJ Montego Bay Sangster Intl
PWMMBJ
Portland
Mon 11/2
6:01 am-4:27 pm
1 stop10h 26m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$198
PortlandMontego Bay
PWM Portland - MBJ Montego Bay Sangster Intl
PWMMBJ
Portland
Sun 11/1
5:20 am-2:25 pm
1 stop9h 05m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$208
PortlandMontego Bay
PWM Portland - MBJ Montego Bay Sangster Intl
PWMMBJ
Portland
Tue 11/10
6:27 am-4:57 pm
2 stops10h 30m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$208
PortlandMontego Bay
PWM Portland - MBJ Montego Bay Sangster Intl
PWMMBJ
Portland
Thu 11/19
6:47 pm-12:17 pm
2 stops17h 30m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$214
Quickest round-trip
PortlandMontego Bay
PWM Portland - MBJ Montego Bay Sangster Intl
PWMMBJ
Portland
Mon 12/7
7:00 am-2:14 pm
1 stop7h 14m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$227
PortlandMontego Bay
PWM Portland - MBJ Montego Bay Sangster Intl
PWMMBJ
Portland
Thu 10/29
7:26 pm-11:18 am
2 stops16h 52m
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
Fri 10/30
7:30 pm-3:19 pm
1 stop20h 49m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$278
PortlandMontego Bay
PWM Portland - MBJ Montego Bay Sangster Intl
PWMMBJ
Portland
Mon 3/1
5:00 pm-12:45 pm
3 stops43h 45m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$306
PortlandMontego Bay
PWM Portland - MBJ Montego Bay Sangster Intl
PWMMBJ
Portland
Thu 11/19
5:50 am-2:14 pm
1 stop8h 24m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$309
Showing 1-10 of 25 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 $419). Flying from Portland, Maine to Jamaica in February is currently the most expensive (average of $1,177). 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 October 24, 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.
Boarding
7.7
Overall
7.3
Crew
8.1
Entertainment
7.1
Food
6.7
Comfort
7.3
Reviews
1 / 20
8.0
ExcellentAsha,Sep 2026
LGA - IAH
Boarding
7.7
Overall
7.3
Crew
8.1
Entertainment
7.1
Food
6.7
Comfort
7.3
Reviews
1 / 20
8.0
ExcellentAsha,Sep 2026
LGA - IAH
Boarding
7.7
Overall
7.3
Crew
8.1
Entertainment
7.1
Food
6.7
Comfort
7.3
Reviews
1 / 20
8.0
ExcellentAsha,Sep 2026
LGA - IAH
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.
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Portland and Jamaica flights
Browse other Portland and Jamaica flight options. Last updated on October 24, 2026.
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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 October 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$352 | Average$648 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$394 | Average$635 | FlexibilityNo cancel fee | On-time69% |