$142+ Cheap flights from Portland (PDX) to Massachusetts
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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — BOS
Jun 2 — Jun 91
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Massachusetts with Cheapflights
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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 MassachusettsExplore the most affordable flight options available from Portland to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 3, 2026.
Explore the most affordable flight options available from Portland to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 3, 2026.
This American Airlines deal was found by Cheapflights users on 4/30. 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 5/2210:40 pm
PDX
- BOS
1 stop8h 21m
American Airlines
Mon 5/256:00 am
BOS
- PDX
1 stop8h 34m
American Airlines
Deal found 4/30![American Airlines logo]()
$262
This American Airlines deal was found by Cheapflights users on 4/30. 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 9/511:20 pm
PDX
- BOS
1 stop8h 10m
American Airlines
Tue 9/153:58 pm
BOS
- PDX
1 stop9h 52m
American Airlines
Deal found 4/30![American Airlines logo]()
$272
This United Airlines deal was found by Cheapflights users on 5/1. 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 5/2910:33 am
PDX
- BOS
1 stop8h 20m
United Airlines
Mon 6/14:15 pm
BOS
- PDX
1 stop8h 33m
United Airlines
Deal found 5/1![United Airlines logo]()
$276
This American Airlines deal was found by Cheapflights users on 4/30. 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 7/810:57 pm
PDX
- BOS
1 stop7h 37m
American Airlines
Sat 7/186:00 am
BOS
- PDX
1 stop8h 33m
American Airlines
Deal found 4/30![American Airlines logo]()
$277
This Flysmarter deal was found by Cheapflights users on 4/30. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/232:30 pm
PDX
- BOS
Nonstop5h 26m
JetBlue
Sat 5/3010:06 am
BOS
- PDX
Nonstop6h 04m
JetBlue
Deal found 4/30![JetBlue logo]()
$279
This lol.travel deal was found by Cheapflights users on 4/30. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/239:46 pm
PDX
- BOS
Nonstop5h 34m
Alaska Airlines
Sat 5/306:00 am
BOS
- PDX
Nonstop6h 11m
Alaska Airlines
Deal found 4/30![Alaska Airlines logo]()
$280
This United Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/610:59 pm
PDX
- BOS
1 stop7h 25m
United Airlines
Tue 11/105:30 am
BOS
- PDX
1 stop9h 55m
United Airlines
Deal found 4/30![United Airlines logo]()
$281
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/282:30 pm
PDX
- BOS
Nonstop5h 26m
JetBlue
Tue 6/210:06 am
BOS
- PDX
Nonstop6h 04m
JetBlue
Deal found 4/30![JetBlue logo]()
$282
This Alaska Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/269:46 pm
PDX
- BOS
Nonstop5h 34m
Alaska Airlines
Tue 6/26:00 am
BOS
- PDX
Nonstop6h 11m
Alaska Airlines
Deal found 4/28![Alaska Airlines logo]()
$287
This Cheapflightsfares deal was found by Cheapflights users on 5/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/232:30 pm
PDX
- BOS
Nonstop5h 26m
JetBlue
Sun 5/2410:06 am
BOS
- PDX
Nonstop6h 04m
JetBlue
Deal found 5/1![JetBlue logo]()
$292
This American Airlines deal was found by Cheapflights users on 5/3. 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.
Tue 8/1811:20 pm
PDX
- ACK
2 stops12h 46m
American Airlines
Wed 8/262:03 pm
ACK
- PDX
2 stops12h 53m
American Airlines
Deal found 5/3![American Airlines logo]()
$293
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2311:12 pm
PDX
- ACK
2 stops9h 15m
Delta
Sat 5/303:00 pm
ACK
- PDX
1 stop9h 00m
Delta
Deal found 4/29![Delta logo]()
$321
Best flights from Portland to MassachusettsDiscover carefully curated flight deals from Portland to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 3, 2026.
Discover carefully curated flight deals from Portland to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 3, 2026.
This United Airlines deal was found by Cheapflights users on 5/1. 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 5/2910:33 am
PDX
- BOS
1 stop8h 20m
United Airlines
Mon 6/14:15 pm
BOS
- PDX
1 stop8h 33m
United Airlines
Deal found 5/1![United Airlines logo]()
$276
This Alaska Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/269:46 pm
PDX
- BOS
Nonstop5h 34m
Alaska Airlines
Tue 6/26:00 am
BOS
- PDX
Nonstop6h 11m
Alaska Airlines
Deal found 4/28![Alaska Airlines logo]()
$287
This Southwest deal was found by Cheapflights users on 5/2. 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 9/17:05 am
PDX
- BOS
2 stops11h 20m
Southwest
Sat 9/55:50 am
BOS
- PDX
1 stop9h 40m
Southwest
Deal found 5/2![Southwest logo]()
$302
This Delta deal was found by Cheapflights users on 4/30. 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 5/2311:12 pm
PDX
- ACK
2 stops12h 07m
Delta
Sat 5/303:00 pm
ACK
- PDX
1 stop9h 00m
Delta
Deal found 4/30![Delta logo]()
$321
This United Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2311:40 pm
PDX
- BOS
2 stops12h 36m
United Airlines
Wed 6/37:28 am
BOS
- PDX
1 stop12h 19m
United Airlines
Deal found 4/29![United Airlines logo]()
$352
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/229:20 pm
PDX
- BOS
1 stop7h 50m
Southwest
Mon 7/275:45 am
BOS
- PDX
1 stop13h 35m
Southwest
Deal found 4/28![Southwest logo]()
$377
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2211:15 pm
PDX
- BOS
2 stops12h 07m
United Airlines
Sat 9/263:35 pm
BOS
- PDX
1 stop8h 38m
United Airlines
Deal found 4/28![United Airlines logo]()
$352
This Southwest deal was found by Cheapflights users on 5/3. 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.
Tue 6/211:55 pm
PDX
- BDL
2 stops9h 15m
Southwest
Tue 6/94:00 pm
BDL
- PDX
2 stops10h 30m
Southwest
Deal found 5/3![Southwest logo]()
$385
This United Airlines deal was found by Cheapflights users on 5/1. 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 8/176:57 pm
PDX
- BOS
2 stops10h 14m
United Airlines
Thu 8/202:03 pm
BOS
- PDX
1 stop11h 57m
United Airlines
Deal found 5/1![United Airlines logo]()
$352
This Expedia deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/279:46 pm
PDX
- HYA
1 stop10h 16m
Multiple Airlines
Wed 6/312:07 pm
HYA
- PDX
2 stops14h 52m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$872
This Delta deal was found by Cheapflights users on 5/1. 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.
Thu 7/911:55 am
PDX
- ALB
1 stop8h 26m
Delta
Tue 7/146:05 am
ALB
- PDX
2 stops9h 33m
Delta
Deal found 5/1![Delta logo]()
$462
This JetBlue deal was found by Cheapflights users on 4/30. 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.
Sat 7/1811:27 pm
PDX
- MVY
1 stop7h 41m
JetBlue
Wed 7/226:44 am
MVY
- PDX
1 stop9h 20m
JetBlue
Deal found 4/30![JetBlue logo]()
$930
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:05 am
PDX
- BOS
2 stops11h 20m
Southwest
Fri 9/188:40 am
BOS
- PDX
2 stops17h 25m
Southwest
Deal found 4/29![Southwest logo]()
$398
This United Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2811:40 pm
PDX
- BDL
1 stop7h 41m
United Airlines
Wed 6/34:50 pm
BDL
- PDX
1 stop10h 03m
United Airlines
Deal found 4/29![United Airlines logo]()
$387
This Delta deal was found by Cheapflights users on 5/1. 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.
Mon 6/811:15 pm
PDX
- MVY
2 stops8h 47m
Delta
Wed 6/101:18 pm
MVY
- PDX
1 stop10h 53m
Delta
Deal found 5/1![Delta logo]()
$490
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:40 pm
PDX
- BOS
2 stops9h 20m
Southwest
Tue 10/201:15 pm
BOS
- PDX
2 stops11h 00m
Southwest
Deal found 4/29![Southwest logo]()
$407
This United Airlines deal was found by Cheapflights users on 5/1. 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 5/2310:40 pm
PDX
- ALB
1 stop9h 03m
United Airlines
Sat 6/66:10 am
ALB
- PDX
1 stop8h 28m
United Airlines
Deal found 5/1![United Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 5/3. 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.
Sat 5/2311:03 pm
PDX
- MVY
1 stop10h 36m
Delta
Sat 5/301:41 pm
MVY
- PDX
1 stop10h 19m
Delta
Deal found 5/3![Delta logo]()
$497
This Southwest deal was found by Cheapflights users on 4/30. 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.
Fri 7/109:20 pm
PDX
- BOS
1 stop11h 35m
Southwest
Fri 7/175:30 pm
BOS
- PDX
1 stop8h 15m
Southwest
Deal found 4/30![Southwest logo]()
$412
This United Airlines deal was found by Cheapflights users on 5/3. 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.
Mon 5/2511:40 pm
PDX
- BDL
1 stop7h 41m
United Airlines
Sat 5/303:02 pm
BDL
- PDX
2 stops10h 29m
United Airlines
Deal found 5/3![United Airlines logo]()
$404
This American Airlines deal was found by Cheapflights users on 5/1. 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.
Tue 6/3010:59 pm
PDX
- MVY
2 stops15h 02m
American Airlines
Sun 7/510:41 am
MVY
- PDX
1 stop15h 49m
American Airlines
Deal found 5/1![American Airlines logo]()
$1,316
This Southwest deal was found by Cheapflights users on 5/3. 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 7/19:20 pm
PDX
- BDL
1 stop7h 45m
Southwest
Wed 7/86:30 pm
BDL
- PDX
1 stop8h 00m
Southwest
Deal found 5/3![Southwest logo]()
$416
This Delta deal was found by Cheapflights users on 5/3. 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.
Mon 7/612:33 am
PDX
- MVY
2 stops11h 26m
Delta
Thu 7/161:18 pm
MVY
- PDX
1 stop10h 55m
Delta
Deal found 5/3![Delta logo]()
$514
This Southwest deal was found by Cheapflights users on 5/2. 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.
Thu 8/67:00 pm
PDX
- BOS
2 stops11h 50m
Southwest
Tue 8/182:45 pm
BOS
- PDX
2 stops10h 30m
Southwest
Deal found 5/2![Southwest logo]()
$422
This United Airlines deal was found by Cheapflights users on 5/2. 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.
Thu 6/410:40 pm
PDX
- BDL
1 stop8h 56m
United Airlines
Thu 6/118:47 am
BDL
- PDX
1 stop10h 10m
United Airlines
Deal found 5/2![United Airlines logo]()
$428
This Delta deal was found by Cheapflights users on 5/3. 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.
Mon 7/612:33 am
PDX
- MVY
2 stops11h 26m
Delta
Fri 7/171:18 pm
MVY
- PDX
1 stop10h 55m
Delta
Deal found 5/3![Delta logo]()
$554
This Southwest deal was found by Cheapflights users on 5/3. 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.
Tue 7/2811:30 pm
PDX
- ALB
2 stops9h 45m
Southwest
Tue 8/113:05 pm
ALB
- PDX
2 stops11h 05m
Southwest
Deal found 5/3![Southwest logo]()
$426
This Expedia deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1711:27 pm
PDX
- MVY
1 stop7h 41m
Multiple Airlines
Wed 7/226:44 am
MVY
- PDX
2 stops12h 52m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$880
This United Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/211:05 am
PDX
- ALB
1 stop9h 25m
United Airlines
Wed 6/36:10 am
ALB
- PDX
1 stop8h 28m
United Airlines
Deal found 4/29![United Airlines logo]()
$485
This Southwest deal was found by Cheapflights users on 5/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/2311:30 pm
PDX
- BDL
1 stop8h 30m
Southwest
Tue 7/146:30 pm
BDL
- PDX
1 stop8h 00m
Southwest
Deal found 5/1![Southwest logo]()
$457
Last-minute flights from Portland to MassachusettsDiscover last-minute flight deals from Portland to Massachusetts. Data last updated May 3, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Massachusetts. Data last updated May 3, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/30. 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 5/2210:40 pm
PDX
- BOS
1 stop8h 21m
American Airlines
Mon 5/256:00 am
BOS
- PDX
1 stop8h 34m
American Airlines
Deal found 4/30![American Airlines logo]()
$262
This American Airlines deal was found by Cheapflights users on 4/30. 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 5/2210:40 pm
PDX
- BOS
1 stop8h 21m
American Airlines
Sun 5/243:10 pm
BOS
- PDX
1 stop11h 13m
American Airlines
Deal found 4/30![American Airlines logo]()
$272
This Flysmarter deal was found by Cheapflights users on 4/30. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/232:30 pm
PDX
- BOS
Nonstop5h 26m
JetBlue
Sat 5/3010:06 am
BOS
- PDX
Nonstop6h 04m
JetBlue
Deal found 4/30![JetBlue logo]()
$279
This lol.travel deal was found by Cheapflights users on 4/30. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/239:46 pm
PDX
- BOS
Nonstop5h 34m
Alaska Airlines
Sat 5/306:00 am
BOS
- PDX
Nonstop6h 11m
Alaska Airlines
Deal found 4/30![Alaska Airlines logo]()
$280
This Cheapflightsfares deal was found by Cheapflights users on 5/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/232:30 pm
PDX
- BOS
Nonstop5h 26m
JetBlue
Sun 5/2410:06 am
BOS
- PDX
Nonstop6h 04m
JetBlue
Deal found 5/1![JetBlue logo]()
$292
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2311:12 pm
PDX
- ACK
2 stops9h 15m
Delta
Sat 5/303:00 pm
ACK
- PDX
1 stop9h 00m
Delta
Deal found 4/29![Delta logo]()
$321
This Alaska Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/269:46 pm
PDX
- BOS
Nonstop5h 34m
Alaska Airlines
Tue 6/26:00 am
BOS
- PDX
Nonstop6h 11m
Alaska Airlines
Deal found 4/28![Alaska Airlines logo]()
$287
This United Airlines deal was found by Cheapflights users on 5/2. 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.
Tue 5/2611:40 pm
PDX
- BDL
1 stop7h 41m
United Airlines
Wed 6/36:09 am
BDL
- PDX
1 stop8h 29m
United Airlines
Deal found 5/2![United Airlines logo]()
$375
This American Airlines deal was found by Cheapflights users on 5/2. 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 5/2610:59 pm
PDX
- BDL
2 stops11h 44m
American Airlines
Wed 6/36:00 pm
BDL
- PDX
1 stop9h 50m
American Airlines
Deal found 5/2![American Airlines logo]()
$380
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/282:30 pm
PDX
- BOS
Nonstop5h 26m
JetBlue
Tue 6/210:06 am
BOS
- PDX
Nonstop6h 04m
JetBlue
Deal found 4/30![JetBlue logo]()
$282
This United Airlines deal was found by Cheapflights users on 5/1. 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 5/2910:33 am
PDX
- BOS
1 stop8h 20m
United Airlines
Mon 6/14:15 pm
BOS
- PDX
1 stop8h 33m
United Airlines
Deal found 5/1![United Airlines logo]()
$276
This Southwest deal was found by Cheapflights users on 5/3. 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.
Fri 5/295:10 am
PDX
- BOS
1 stop14h 10m
Southwest
Mon 6/16:55 pm
BOS
- PDX
1 stop8h 15m
Southwest
Deal found 5/3![Southwest logo]()
$277
One-way flights from Portland to MassachusettsSearch for one-way flight options from Portland to Massachusetts. Find affordable one-way fares based on user searches. Data last updated May 3, 2026.
Search for one-way flight options from Portland to Massachusetts. Find affordable one-way fares based on user searches. Data last updated May 3, 2026.
This Super.com deal was found by Cheapflights users on 4/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/262:30 pm
PDX
- BOS
Nonstop5h 26m
JetBlue
Deal found 4/30![JetBlue logo]()
$142
This JetBlue deal was found by Cheapflights users on 4/30. 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.
Thu 5/282:30 pm
PDX
- BOS
Nonstop5h 26m
JetBlue
Deal found 4/30![JetBlue logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/95:20 pm
PDX
- BOS
2 stops29h 07m
Frontier
Deal found 4/28![Frontier logo]()
$145
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1911:29 pm
PDX
- BOS
Nonstop5h 23m
JetBlue
Deal found 4/30![JetBlue logo]()
$149
This American Airlines deal was found by Cheapflights users on 4/30. 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 5/2510:40 pm
PDX
- BOS
1 stop8h 21m
American Airlines
Deal found 4/30![American Airlines logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Tue 7/287:00 am
PDX
- BOS
Nonstop5h 30m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$156
This United Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/710:40 pm
PDX
- BOS
1 stop7h 59m
United Airlines
Deal found 4/29![United Airlines logo]()
$157
This United Airlines deal was found by Cheapflights users on 5/3. 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.
Tue 6/2310:40 pm
PDX
- BOS
1 stop7h 49m
United Airlines
Deal found 5/3![United Airlines logo]()
$158
This United Airlines deal was found by Cheapflights users on 5/1. 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.
Thu 6/1810:52 pm
PDX
- BOS
1 stop9h 24m
United Airlines
Deal found 5/1![United Airlines logo]()
$161
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1310:55 pm
PDX
- BOS
1 stop7h 30m
United Airlines
Deal found 4/28![United Airlines logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Tue 6/25:46 pm
PDX
- BDL
2 stops22h 06m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 5/118:46 pm
PDX
- BDL
1 stop30h 34m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$174
Find flight deals from Portland to Massachusetts
Keep the following information in mind while searching for Portland to Massachusetts flight deals. Data was last updated May 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $262 (American Airlines) |
One-way from | $142 (Super.com) |
Popular in | December |
Cheapest in | August |
Average price | $336 |
Good round-trip deal | $354 or less |
Good one-way deal | $158 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to Massachusetts 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 May 3, 2026.
Use the filters below to find and compare flights from Portland to Massachusetts that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandBoston
PDX - BOS
PDXBOS
Portland
Fri 5/29
10:33 am-9:53 pm
1 stop8h 20m
Boston Logan Intl
Mon 6/1
4:15 pm-9:48 pm
1 stop8h 33m
$276
Quickest round-trip
PortlandBoston
PDX - BOS
PDXBOS
Portland
Tue 5/26
9:46 pm-6:20 am
Nonstop5h 34m
Boston Logan Intl
Tue 6/2
6:00 am-9:11 am
Nonstop6h 11m
$287
PortlandBoston
PDX - BOS
PDXBOS
Portland
Tue 9/1
7:05 am-9:25 pm
2 stops11h 20m
Boston Logan Intl
Sat 9/5
5:50 am-12:30 pm
1 stop9h 40m
$302
PortlandNantucket
PDX - ACK
PDXACK
Portland
Sat 5/23
11:12 pm-2:19 pm
2 stops12h 07m
Nantucket Memorial
Sat 5/30
3:00 pm-9:00 pm
1 stop9h 00m
$321
PortlandBoston
PDX - BOS
PDXBOS
Portland
Sat 5/23
11:40 pm-3:16 pm
2 stops12h 36m
Boston Logan Intl
Wed 6/3
7:28 am-4:47 pm
1 stop12h 19m
$352
PortlandBoston
PDX - BOS
PDXBOS
Portland
Tue 9/22
11:15 pm-2:22 pm
2 stops12h 07m
Boston Logan Intl
Sat 9/26
3:35 pm-9:13 pm
1 stop8h 38m
$352
PortlandBoston
PDX - BOS
PDXBOS
Portland
Mon 8/17
6:57 pm-8:11 am
2 stops10h 14m
Boston Logan Intl
Thu 8/20
2:03 pm-11:00 pm
1 stop11h 57m
$352
PortlandBoston
PDX - BOS
PDXBOS
Portland
Wed 7/22
9:20 pm-8:10 am
1 stop7h 50m
Boston Logan Intl
Mon 7/27
5:45 am-4:20 pm
1 stop13h 35m
$377
PortlandHartford
PDX - BDL
PDXBDL
Portland
Tue 6/2
11:55 pm-12:10 pm
2 stops9h 15m
Hartford Bradley Intl
Tue 6/9
4:00 pm-11:30 pm
2 stops10h 30m
$385
PortlandHartford
PDX - BDL
PDXBDL
Portland
Thu 5/28
11:40 pm-10:21 am
1 stop7h 41m
Hartford Bradley Intl
Wed 6/3
4:50 pm-11:53 pm
1 stop10h 03m
$387
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Portland to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Portland with our price prediction graph.
PDX-BOS
PDX-BDL
PDX-ALB
PDX-MVY
PDX-ACK
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 Massachusetts
PDX-USMA
PDX-BOS
PDX-BDL
PDX-ALB
PDX-MVY
How far ahead should I book a flight from Portland to Massachusetts?
Booking 62 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland to Massachusetts. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Portland to Massachusetts?
Currently, March is the cheapest month in which you can book a flight from Portland to Massachusetts (average of $98). Flying from Portland to Massachusetts in January is currently the most expensive (average of $142). 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 PDX to MA?
Find hourly flight availability from Portland to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 3, 2026.
It’s typically best to fly out from Portland to Massachusetts in the evening. Doing so could potentially save you 29% on the flight price compared to flying in the morning, which is usually more expensive.
How much does it cost to fly round-trip from Portland to Massachusetts?
Reviews of airlines servicing Massachusetts
Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated May 3, 2026.
Peruse reviews from past customers who have flown with Alaska Airlines,Delta, andHawaiian Airlines from Portland to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Comfort
7.8
Crew
8.5
Food
7.1
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Boarding
8.1
Comfort
7.8
Crew
8.5
Food
7.1
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Boarding
8.1
Comfort
7.8
Crew
8.5
Food
7.1
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Boarding
8.1
Comfort
7.8
Crew
8.5
Food
7.1
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Boarding
8.1
Comfort
7.8
Crew
8.5
Food
7.1
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Boarding
8.1
Comfort
7.8
Crew
8.5
Food
7.1
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Related info for your journey
Find useful and relevant information for your journey from Portland to Massachusetts. 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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Alternative routes for Portland to Massachusetts
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Complete your trip
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Find flights from Portland to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Portland and Massachusetts flights
Browse other Portland and Massachusetts flight options. Last updated on May 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Portland to Massachusetts flights
Consider these flights traveling from Portland to Massachusetts.
Top 7 airlines flying from Portland to Massachusetts
Discover the top 7 airlines that operate flights from Portland to Massachusetts. 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 May 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$341 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$108 | Average$277 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$108 | Average$313 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$276 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$184 | Average$389 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$236 | Average$378 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$255 | Average$486 | FlexibilityNo cancel fee | On-time75% |