$132+ Cheap flights from Massachusetts to Portland, ME (PWM)
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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — PWM
Mar 7 — Mar 141
1 adult, Economy
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Find cheap flights from Massachusetts to Portland 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
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Cheapest flights from Massachusetts to PortlandExplore the most affordable flight options available from Massachusetts to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 5, 2026.
Explore the most affordable flight options available from Massachusetts to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/4. 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.
Sun 8/238:00 am
BDL
- PWM
1 stop11h 16m
Breeze Airways
Thu 8/277:56 pm
PWM
- BDL
1 stop25h 39m
Breeze Airways
Deal found 2/4![Breeze Airways logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 2/4. 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.
Sun 8/238:00 am
BDL
- PWM
1 stop11h 16m
Breeze Airways
Fri 8/286:13 pm
PWM
- BDL
1 stop28h 59m
Breeze Airways
Deal found 2/4![Breeze Airways logo]()
$297
This Delta deal was found by Cheapflights users on 2/4. 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.
Tue 9/85:30 am
ALB
- PWM
1 stop5h 31m
Delta
Tue 9/155:59 pm
PWM
- ALB
1 stop4h 53m
Delta
Deal found 2/4![Delta logo]()
$315
This American Airlines deal was found by Cheapflights users on 2/3. 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.
Wed 4/156:00 am
BOS
- PWM
1 stop9h 09m
American Airlines
Wed 4/223:39 pm
PWM
- BOS
1 stop7h 15m
American Airlines
Deal found 2/3![American Airlines logo]()
$323
This Southwest deal was found by Cheapflights users on 2/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/189:05 am
BDL
- PWM
1 stop6h 50m
Southwest
Wed 4/14:30 pm
PWM
- BDL
1 stop6h 25m
Southwest
Deal found 2/4![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 2/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/95:35 pm
ALB
- PWM
1 stop6h 30m
Southwest
Mon 3/165:30 pm
PWM
- ALB
1 stop6h 45m
Southwest
Deal found 2/4![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 2/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:00 am
ALB
- PWM
1 stop6h 25m
Southwest
Tue 9/1510:30 am
PWM
- ALB
2 stops10h 50m
Southwest
Deal found 2/4![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 2/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1310:15 am
ALB
- PWM
1 stop4h 45m
Southwest
Mon 8/175:55 am
PWM
- ALB
1 stop3h 35m
Southwest
Deal found 2/3![Southwest logo]()
$337
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/35:35 am
ALB
- PWM
1 stop5h 43m
Delta
Tue 3/105:48 pm
PWM
- ALB
1 stop5h 12m
Delta
Deal found 2/2![Delta logo]()
$341
This Kiwi.com deal was found by Cheapflights users on 2/4. 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.
Sun 8/238:00 am
BDL
- PWM
1 stop11h 16m
Breeze Airways
Sat 8/295:01 pm
PWM
- BDL
1 stop22h 19m
Breeze Airways
Deal found 2/4![Breeze Airways logo]()
$342
This American Airlines deal was found by Cheapflights users on 2/2. 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.
Fri 5/227:31 pm
BOS
- PWM
1 stop17h 10m
American Airlines
Sun 5/241:31 pm
PWM
- BOS
1 stop8h 33m
American Airlines
Deal found 2/2![American Airlines logo]()
$343
This Southwest deal was found by Cheapflights users on 2/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/33:40 pm
ALB
- PWM
1 stop6h 35m
Southwest
Tue 3/105:30 am
PWM
- ALB
1 stop6h 15m
Southwest
Deal found 2/2![Southwest logo]()
$347
Best flights from Massachusetts to PortlandDiscover carefully curated flight deals from Massachusetts to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 5, 2026.
Discover carefully curated flight deals from Massachusetts to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 5, 2026.
This American Airlines deal was found by Cheapflights users on 2/3. 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.
Wed 4/156:00 am
BOS
- PWM
1 stop9h 09m
American Airlines
Wed 4/223:39 pm
PWM
- BOS
1 stop7h 15m
American Airlines
Deal found 2/3![American Airlines logo]()
$323
This Southwest deal was found by Cheapflights users on 2/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/189:05 am
BDL
- PWM
1 stop6h 50m
Southwest
Wed 4/14:30 pm
PWM
- BDL
1 stop6h 25m
Southwest
Deal found 2/4![Southwest logo]()
$327
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/35:35 am
ALB
- PWM
1 stop5h 43m
Delta
Tue 3/105:48 pm
PWM
- ALB
1 stop5h 12m
Delta
Deal found 2/2![Delta logo]()
$341
This Southwest deal was found by Cheapflights users on 2/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/95:35 pm
ALB
- PWM
1 stop6h 30m
Southwest
Mon 3/165:30 pm
PWM
- ALB
1 stop6h 45m
Southwest
Deal found 2/4![Southwest logo]()
$327
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/17:30 am
BOS
- PWM
2 stops15h 50m
Delta
Sat 3/71:15 pm
PWM
- BOS
2 stops18h 23m
Delta
Deal found 2/2![Delta logo]()
$355
This Southwest deal was found by Cheapflights users on 2/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/33:40 pm
ALB
- PWM
1 stop6h 35m
Southwest
Tue 3/105:30 am
PWM
- ALB
1 stop6h 15m
Southwest
Deal found 2/2![Southwest logo]()
$347
This American Airlines deal was found by Cheapflights users on 2/4. 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 3/1811:33 am
BDL
- PWM
2 stops12h 22m
American Airlines
Wed 4/16:00 am
PWM
- BDL
1 stop10h 52m
American Airlines
Deal found 2/4![American Airlines logo]()
$411
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/26:00 am
BOS
- PWM
1 stop7h 43m
Delta
Sat 3/71:15 pm
PWM
- BOS
2 stops18h 23m
Delta
Deal found 2/2![Delta logo]()
$395
This United Airlines deal was found by Cheapflights users on 2/2. 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 2/183:00 pm
BDL
- PWM
2 stops8h 20m
United Airlines
Thu 2/193:05 pm
PWM
- BDL
2 stops8h 54m
United Airlines
Deal found 2/2![United Airlines logo]()
$925
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/276:00 am
BOS
- PWM
1 stop18h 18m
Delta
Wed 3/46:30 am
PWM
- BOS
1 stop11h 51m
Delta
Deal found 2/2![Delta logo]()
$395
This American Airlines deal was found by Cheapflights users on 2/5. 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.
Thu 4/96:00 am
ALB
- PWM
1 stop17h 54m
American Airlines
Mon 4/135:02 pm
PWM
- ALB
1 stop18h 30m
American Airlines
Deal found 2/5![American Airlines logo]()
$468
This Southwest deal was found by Cheapflights users on 2/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/189:25 am
BDL
- PWM
1 stop5h 30m
Southwest
Thu 2/195:35 am
PWM
- BDL
1 stop6h 00m
Southwest
Deal found 2/2![Southwest logo]()
$431
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/276:00 am
BOS
- PWM
1 stop18h 18m
Delta
Thu 3/52:35 pm
PWM
- BOS
1 stop16h 55m
Delta
Deal found 2/2![Delta logo]()
$395
This American Airlines deal was found by Cheapflights users on 2/4. 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.
Mon 3/96:00 am
ALB
- PWM
2 stops12h 04m
American Airlines
Mon 3/1612:44 pm
PWM
- ALB
2 stops11h 00m
American Airlines
Deal found 2/4![American Airlines logo]()
$468
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:00 am
BOS
- PWM
1 stop18h 18m
Delta
Sat 3/71:15 pm
PWM
- BOS
2 stops18h 23m
Delta
Deal found 2/2![Delta logo]()
$395
This Southwest deal was found by Cheapflights users on 2/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/183:40 pm
ALB
- PWM
1 stop6h 35m
Southwest
Sun 2/224:50 pm
PWM
- ALB
1 stop4h 15m
Southwest
Deal found 2/3![Southwest logo]()
$465
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/276:00 am
BOS
- PWM
1 stop18h 18m
Delta
Fri 3/65:59 pm
PWM
- BOS
1 stop13h 29m
Delta
Deal found 2/2![Delta logo]()
$400
This American Airlines deal was found by Cheapflights users on 2/3. 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.
Fri 5/86:00 am
ALB
- PWM
2 stops10h 40m
American Airlines
Mon 5/1110:47 am
PWM
- ALB
2 stops12h 37m
American Airlines
Deal found 2/3![American Airlines logo]()
$489
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:53 pm
BOS
- PWM
1 stop18h 50m
Delta
Sat 3/71:15 pm
PWM
- BOS
2 stops18h 23m
Delta
Deal found 2/2![Delta logo]()
$409
This United Airlines deal was found by Cheapflights users on 2/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/183:00 pm
BDL
- PWM
1 stop3h 56m
United Airlines
Sun 2/229:40 am
PWM
- BDL
1 stop4h 24m
United Airlines
Deal found 2/3![United Airlines logo]()
$1,233
This American Airlines deal was found by Cheapflights users on 2/3. 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.
Wed 2/185:28 am
BDL
- PWM
1 stop18h 22m
American Airlines
Thu 2/196:00 am
PWM
- BDL
1 stop26h 12m
American Airlines
Deal found 2/3![American Airlines logo]()
$1,025
Last-minute flights from Massachusetts to PortlandDiscover last-minute flight deals from Massachusetts to Portland. Data last updated February 5, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Portland. Data last updated February 5, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/276:00 am
BOS
- PWM
1 stop18h 18m
Delta
Thu 3/52:35 pm
PWM
- BOS
1 stop16h 55m
Delta
Deal found 2/2![Delta logo]()
$395
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/276:00 am
BOS
- PWM
1 stop18h 18m
Delta
Fri 3/65:59 pm
PWM
- BOS
1 stop13h 29m
Delta
Deal found 2/2![Delta logo]()
$400
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:53 pm
BOS
- PWM
1 stop18h 50m
Delta
Sat 3/71:15 pm
PWM
- BOS
2 stops18h 23m
Delta
Deal found 2/2![Delta logo]()
$409
This United Airlines deal was found by Cheapflights users on 2/2. 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 2/285:35 am
BOS
- PWM
2 stops17h 45m
United Airlines
Wed 3/43:05 pm
PWM
- BOS
2 stops18h 53m
United Airlines
Deal found 2/2![United Airlines logo]()
$416
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:53 pm
BOS
- PWM
1 stop18h 50m
Delta
Fri 3/65:59 pm
PWM
- BOS
1 stop13h 29m
Delta
Deal found 2/2![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/17:30 am
BOS
- PWM
2 stops15h 50m
Delta
Sat 3/71:15 pm
PWM
- BOS
2 stops18h 23m
Delta
Deal found 2/2![Delta logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/110:01 am
BOS
- PWM
1 stop24h 48m
Multiple Airlines
Wed 3/46:18 pm
PWM
- BOS
2 stops29h 26m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$408
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/35:35 am
ALB
- PWM
1 stop5h 43m
Delta
Tue 3/105:48 pm
PWM
- ALB
1 stop5h 12m
Delta
Deal found 2/2![Delta logo]()
$341
This Southwest deal was found by Cheapflights users on 2/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/33:40 pm
ALB
- PWM
1 stop6h 35m
Southwest
Tue 3/105:30 am
PWM
- ALB
1 stop6h 15m
Southwest
Deal found 2/2![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 2/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/95:35 pm
ALB
- PWM
1 stop6h 30m
Southwest
Mon 3/165:30 pm
PWM
- ALB
1 stop6h 45m
Southwest
Deal found 2/4![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 2/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/189:05 am
BDL
- PWM
1 stop6h 50m
Southwest
Wed 4/14:30 pm
PWM
- BDL
1 stop6h 25m
Southwest
Deal found 2/4![Southwest logo]()
$327
This American Airlines deal was found by Cheapflights users on 2/4. 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 3/1811:33 am
BDL
- PWM
2 stops12h 22m
American Airlines
Wed 4/16:00 am
PWM
- BDL
1 stop10h 52m
American Airlines
Deal found 2/4![American Airlines logo]()
$411
One-way flights from Massachusetts to PortlandSearch for one-way flight options from Massachusetts to Portland. Find affordable one-way fares based on user searches. Data last updated February 5, 2026.
Search for one-way flight options from Massachusetts to Portland. Find affordable one-way fares based on user searches. Data last updated February 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/298:17 pm
ALB
- PWM
1 stop19h 59m
Breeze Airways
Deal found 2/2![Breeze Airways logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 2/4. 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.
Sun 3/812:56 pm
BOS
- PWM
1 stop21h 53m
Multiple Airlines
Deal found 2/4![Multiple Airlines logo]()
$146
This Southwest deal was found by Cheapflights users on 2/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/105:55 am
BDL
- PWM
1 stop6h 00m
Southwest
Deal found 2/2![Southwest logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/185:49 pm
BOS
- PWM
2 stops41h 00m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:53 pm
ALB
- PWM
2 stops42h 33m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1910:01 am
BOS
- PWM
1 stop24h 48m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$238
This American Airlines deal was found by Cheapflights users on 2/2. 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 3/105:28 am
BDL
- PWM
2 stops12h 36m
American Airlines
Deal found 2/2![American Airlines logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 2/4. 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.
Mon 3/165:49 pm
BOS
- PWM
2 stops40h 28m
Multiple Airlines
Deal found 2/4![Multiple Airlines logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 2/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/214:01 pm
BDL
- PWM
2 stops42h 48m
Breeze Airways
Deal found 2/5![Breeze Airways logo]()
$299
This American Airlines deal was found by Cheapflights users on 2/5. 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.
Fri 3/202:40 pm
BOS
- PWM
1 stop21h 34m
American Airlines
Deal found 2/5![American Airlines logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 2/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/2012:35 pm
BOS
- PWM
2 stops21h 42m
Multiple Airlines
Deal found 2/5![Multiple Airlines logo]()
$316
This Southwest deal was found by Cheapflights users on 2/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:30 am
BDL
- PWM
1 stop4h 55m
Southwest
Deal found 2/5![Southwest logo]()
$384
Find flight deals from Massachusetts to Portland
Keep the following information in mind while searching for Massachusetts to Portland flight deals. Data was last updated February 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $323 (American Airlines) |
One-way from | $132 (Kiwi.com) |
Cheapflights Fare Finder
Customize your flight search to find flights from Massachusetts to Portland 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 February 5, 2026.
Use the filters below to find and compare flights from Massachusetts to Portland that are best for you.
Fly from
Massachusetts
Fly to
Portland
Route
Depart
Return
Price
BostonPortland
BOS - PWM
BOSPWM
Boston Logan Intl
Wed 4/15
6:00 am-3:09 pm
1 stop9h 09m
Portland
Wed 4/22
3:39 pm-10:54 pm
1 stop7h 15m
$323
HartfordPortland
BDL - PWM
BDLPWM
Hartford Bradley Intl
Wed 3/18
9:05 am-3:55 pm
1 stop6h 50m
Portland
Wed 4/1
4:30 pm-10:55 pm
1 stop6h 25m
$327
AlbanyPortland
ALB - PWM
ALBPWM
Albany Intl
Mon 3/9
5:35 pm-12:05 am
1 stop6h 30m
Portland
Mon 3/16
5:30 pm-12:15 am
1 stop6h 45m
$327
AlbanyPortland
ALB - PWM
ALBPWM
Albany Intl
Tue 3/3
5:35 am-11:18 am
1 stop5h 43m
Portland
Tue 3/10
5:48 pm-11:00 pm
1 stop5h 12m
$341
AlbanyPortland
ALB - PWM
ALBPWM
Albany Intl
Tue 3/3
3:40 pm-10:15 pm
1 stop6h 35m
Portland
Tue 3/10
5:30 am-11:45 am
1 stop6h 15m
$347
BostonPortland
BOS - PWM
BOSPWM
Boston Logan Intl
Sun 3/1
7:30 am-11:20 pm
2 stops15h 50m
Portland
Sat 3/7
1:15 pm-7:38 am
2 stops18h 23m
$355
BostonPortland
BOS - PWM
BOSPWM
Boston Logan Intl
Mon 3/2
6:00 am-1:43 pm
1 stop7h 43m
Portland
Sat 3/7
1:15 pm-7:38 am
2 stops18h 23m
$395
BostonPortland
BOS - PWM
BOSPWM
Boston Logan Intl
Fri 2/27
6:00 am-12:18 am
1 stop18h 18m
Portland
Wed 3/4
6:30 am-6:21 pm
1 stop11h 51m
$395
BostonPortland
BOS - PWM
BOSPWM
Boston Logan Intl
Fri 2/27
6:00 am-12:18 am
1 stop18h 18m
Portland
Thu 3/5
2:35 pm-7:30 am
1 stop16h 55m
$395
BostonPortland
BOS - PWM
BOSPWM
Boston Logan Intl
Tue 3/3
6:00 am-12:18 am
1 stop18h 18m
Portland
Sat 3/7
1:15 pm-7:38 am
2 stops18h 23m
$395
Showing 1-10 of 36 results
Best time to book a flight from Massachusetts to Portland
Have a flexible travel schedule? Discover the best time to fly to Portland from Massachusetts with our price prediction graph.
ALB-PWM
BOS-PWM
BDL-PWM
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 Massachusetts to Portland
USMA-PWM
ALB-PWM
BOS-PWM
BDL-PWM
No data available for this route at this time. Please check back soon.
Related info for your journey
Find useful and relevant information for your journey from Massachusetts to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Portland?
Book flights to Portland if you plan to visit one of these locationsNorth Conway
Brunswick
Auburn
Conway
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