$208+ Cheap flights from Portland (PDX) to Massachusetts
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 1/4. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — BOS
Dec 14 — Dec 211
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Portland to Massachusetts with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Portland to Massachusetts
Cheapest
Best
Last-minute
One-way
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 November 14, 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 November 14, 2026.
This Alaska Airlines deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:59 pm -
1 stop18h 09m
Tue 12/86:13 pm -
1 stop18h 37m
Deal found 11/9![Alaska Airlines logo]()
$351
This Alaska Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/87:59 pm -
1 stop18h 10m
Tue 12/156:13 pm -
1 stop18h 37m
Deal found 11/10![Alaska Airlines logo]()
$355
This Alaska Airlines deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:59 pm -
1 stop18h 09m
Mon 12/76:13 pm -
1 stop18h 37m
Deal found 11/9![Alaska Airlines logo]()
$357
This Alaska Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/87:59 pm -
1 stop18h 10m
Mon 12/146:13 pm -
1 stop18h 37m
Deal found 11/10![Alaska Airlines logo]()
$361
This Alaska Airlines deal was found by Cheapflights users on 11/13. 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 12/157:59 pm -
1 stop18h 10m
Tue 1/124:55 pm -
1 stop26h 51m
Deal found 11/13![Alaska Airlines logo]()
$365
This Expedia deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/117:59 pm -
1 stop18h 09m
Tue 12/156:13 pm -
1 stop22h 25m
Deal found 11/10![Alaska Airlines logo]()
$370
This Alaska Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/82:51 pm -
1 stop23h 18m
Fri 12/116:13 pm -
1 stop25h 37m
Deal found 11/10![Alaska Airlines logo]()
$371
This Alaska Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/87:59 pm -
1 stop18h 10m
Wed 12/166:13 pm -
1 stop18h 16m
Deal found 11/10![Alaska Airlines logo]()
$375
This Alaska Airlines deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:59 pm -
1 stop18h 09m
Tue 12/86:13 pm -
1 stop18h 37m
Deal found 11/9![Alaska Airlines logo]()
$376
This Alaska Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:59 pm -
1 stop18h 09m
Fri 12/116:13 pm -
1 stop22h 25m
Deal found 11/10![Alaska Airlines logo]()
$377
This Alaska Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:00 am -
1 stop31h 08m
Wed 12/96:13 pm -
1 stop25h 37m
Deal found 11/10![Alaska Airlines logo]()
$381
This Alaska Airlines deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:59 pm -
1 stop18h 09m
Thu 12/106:13 pm -
1 stop18h 37m
Deal found 11/9![Alaska Airlines logo]()
$382
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 November 14, 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 November 14, 2026.
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/75:48 pm -
1 stop10h 03m
Mon 1/117:35 am -
1 stop10h 57m
Deal found 11/9![Delta logo]()
$447
This Southwest deal was found by Cheapflights users on 11/11. 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 12/36:00 am -
1 stop7h 20m
Wed 12/95:20 am -
2 stops10h 50m
Deal found 11/11![Southwest logo]()
$452
This United Airlines deal was found by Cheapflights users on 11/12. 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 3/186:59 pm -
1 stop7h 55m
Mon 3/296:33 pm -
1 stop8h 24m
Deal found 11/12![United Airlines logo]()
$457
This Alaska Airlines deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/77:27 am -
Nonstop5h 26m
Mon 1/114:55 pm -
1 stop26h 51m
Deal found 11/9![Alaska Airlines logo]()
$461
This Southwest deal was found by Cheapflights users on 11/12. 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 5/77:55 pm -
2 stops9h 30m
Sat 5/1510:15 am -
2 stops11h 10m
Deal found 11/12![Southwest logo]()
$457
This Alaska Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/257:15 am -
Nonstop5h 28m
Mon 1/45:47 pm -
1 stop29h 47m
Deal found 11/10![Alaska Airlines logo]()
$466
This Southwest deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/155:15 am -
2 stops10h 50m
Sun 1/171:15 pm -
2 stops12h 05m
Deal found 11/10![Southwest logo]()
$457
This United Airlines deal was found by Cheapflights users on 11/13. 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 12/2811:42 pm -
1 stop7h 38m
Fri 1/15:45 am -
1 stop9h 02m
Deal found 11/13![United Airlines logo]()
$510
This Alaska Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/209:22 pm -
1 stop29h 06m
Sun 1/36:00 am -
Nonstop6h 40m
Deal found 11/10![Alaska Airlines logo]()
$471
This Alaska Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/87:29 am -
Nonstop5h 24m
Tue 12/154:56 pm -
Nonstop6h 33m
Deal found 11/10![Alaska Airlines logo]()
$497
This Southwest deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1311:30 pm -
2 stops9h 50m
Thu 12/315:00 am -
1 stop8h 40m
Deal found 11/9![Southwest logo]()
$502
This Southwest deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:55 am -
2 stops12h 00m
Sat 12/57:15 am -
1 stop8h 45m
Deal found 11/10![Southwest logo]()
$511
Last-minute flights from Portland to MassachusettsDiscover last-minute flight deals from Portland to Massachusetts. Data last updated November 14, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Massachusetts. Data last updated November 14, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:59 pm -
1 stop18h 09m
Tue 12/86:13 pm -
1 stop18h 37m
Deal found 11/9![Alaska Airlines logo]()
$351
This Alaska Airlines deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:59 pm -
1 stop18h 09m
Mon 12/76:13 pm -
1 stop18h 37m
Deal found 11/9![Alaska Airlines logo]()
$357
This Alaska Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:59 pm -
1 stop18h 09m
Fri 12/116:13 pm -
1 stop22h 25m
Deal found 11/10![Alaska Airlines logo]()
$377
This Alaska Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:00 am -
1 stop31h 08m
Wed 12/96:13 pm -
1 stop25h 37m
Deal found 11/10![Alaska Airlines logo]()
$381
This Alaska Airlines deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:59 pm -
1 stop18h 09m
Thu 12/106:13 pm -
1 stop18h 37m
Deal found 11/9![Alaska Airlines logo]()
$382
This Alaska Airlines deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:59 pm -
1 stop18h 09m
Tue 12/86:13 pm -
1 stop18h 37m
Deal found 11/9![Alaska Airlines logo]()
$376
This Alaska Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/87:59 pm -
1 stop18h 10m
Tue 12/156:13 pm -
1 stop18h 37m
Deal found 11/10![Alaska Airlines logo]()
$355
This Alaska Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/87:59 pm -
1 stop18h 10m
Mon 12/146:13 pm -
1 stop18h 37m
Deal found 11/10![Alaska Airlines logo]()
$361
This Alaska Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/82:51 pm -
1 stop23h 18m
Fri 12/116:13 pm -
1 stop25h 37m
Deal found 11/10![Alaska Airlines logo]()
$371
This Alaska Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/87:59 pm -
1 stop18h 10m
Wed 12/166:13 pm -
1 stop18h 16m
Deal found 11/10![Alaska Airlines logo]()
$375
This Expedia deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/117:59 pm -
1 stop18h 09m
Tue 12/156:13 pm -
1 stop22h 25m
Deal found 11/10![Alaska Airlines logo]()
$370
This Alaska Airlines deal was found by Cheapflights users on 11/13. 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 12/157:59 pm -
1 stop18h 10m
Tue 1/124:55 pm -
1 stop26h 51m
Deal found 11/13![Alaska Airlines logo]()
$365
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 November 14, 2026.
Search for one-way flight options from Portland to Massachusetts. Find affordable one-way fares based on user searches. Data last updated November 14, 2026.
This Alaska Airlines deal was found by Cheapflights users on 11/13. 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.
Mon 1/42:52 pm -
1 stop22h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/13![Alaska Airlines logo]()
$208
This Alaska Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/177:05 am -
1 stop19h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Alaska Airlines logo]()
$209
This Booking.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/162:41 pm -
2 stops11h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Alaska Airlines logo]()
$211
This Booking.com deal was found by Cheapflights users on 11/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/112:53 pm -
1 stop21h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/11![Alaska Airlines logo]()
$213
This Expedia deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/212:52 pm -
1 stop11h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Alaska Airlines logo]()
$219
This Alaska Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/37:02 am -
1 stop29h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Alaska Airlines logo]()
$223
This United Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1811:50 pm -
1 stop7h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![United Airlines logo]()
$224
This Southwest deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/96:00 am -
2 stops9h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Southwest logo]()
$228
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/611:10 pm -
1 stop10h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Delta logo]()
$229
This Southwest deal was found by Cheapflights users on 11/12. 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 12/86:55 am -
2 stops12h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/12![Southwest logo]()
$233
This Southwest deal was found by Cheapflights users on 11/13. 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 12/1311:30 pm -
2 stops9h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/13![Southwest logo]()
$234
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 November 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $351 (Alaska Airlines) |
One-way from | $208 (Alaska Airlines) |
Popular in | December |
Cheapest in | January |
Average price | $565 |
Good round-trip deal | $497 or less |
Good one-way deal | $243 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 7,457,451 searches. Data last updated November 14, 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
Quickest round-trip
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Wed 12/23
11:50 pm-10:17 am
1 stop7h 27m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$223
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Sun 5/2
4:15 pm-6:40 am
1 stop11h 25m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$224
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Thu 3/4
7:05 am-6:58 pm
1 stop8h 53m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$224
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Thu 12/24
11:55 am-11:38 pm
1 stop8h 43m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$224
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Sat 3/6
10:56 pm-9:50 am
1 stop7h 54m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$224
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Sun 1/31
6:00 am-7:05 pm
2 stops10h 05m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$229
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Sat 12/19
12:26 pm-12:12 am
1 stop8h 46m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$229
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Fri 12/18
11:50 pm-10:17 am
1 stop7h 27m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$229
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Tue 1/5
10:15 am-11:45 pm
2 stops10h 30m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$229
PortlandBoston
PDX Portland - BOS Boston Logan Intl
PDXBOS
Portland
Sun 5/9
1:38 pm-12:20 am
1 stop7h 42m
Boston Logan Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$229
Showing 1-10 of 23 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
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
What is the cheapest month to book a flight from Portland to Massachusetts?
Currently, January is the cheapest month in which you can book a flight from Portland to Massachusetts (average of $337). Flying from Portland to Massachusetts in December is currently the most expensive (average of $568). 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 November 14, 2026.
It’s typically best to fly out from Portland to Massachusetts at noon. Doing so could potentially save you 33% 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?
Airfare is below average for this route at the moment.
Portland to Massachusetts flights typically cost between $448 and $704 in December.The cheapest round-trip price found within the last 5 days was $351 on Alaska Airlines (Dec 2-Dec 8).
How far ahead should I book a flight from Portland to Massachusetts?
Booking 90 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.
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 November 14, 2026.
Peruse reviews from past customers who have flown with Alaska Airlines,Delta, andUnited 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.
Overall
7.9
Crew
8.5
Boarding
8.1
Food
7.0
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Overall
7.9
Crew
8.5
Boarding
8.1
Food
7.0
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Overall
7.9
Crew
8.5
Boarding
8.1
Food
7.0
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Overall
7.9
Crew
8.5
Boarding
8.1
Food
7.0
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Overall
7.9
Crew
8.5
Boarding
8.1
Food
7.0
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
Overall
7.9
Crew
8.5
Boarding
8.1
Food
7.0
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Nov 2025
PDX - BNA
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for Portland to Massachusetts
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Portland to Massachusetts by cabin class
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 November 14, 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 6 airlines flying from Portland to Massachusetts
Discover the top 6 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 7,457,451 searches. Data last updated November 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$109 | Average$305 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$179 | Average$367 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$227 | Average$365 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$236 | Average$412 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$236 | Average$378 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$286 | Average$525 | FlexibilityNo cancel fee | On-time75% |