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Massachusetts

$114+ Cheap flights from Portland, ME (PWM) 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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — BOS
Aug 11 — Aug 181
Tue 8/11
Tue 8/18
1 adult, Economy
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Cheap flight deals from Portland to Massachusetts

Cheapest flights from Portland to Massachusetts
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 July 12, 2026.

This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/135:55 am
PWM
-
BOS
1 stop3h 55m
Southwest
Sat 8/154:35 pm
BOS
-
PWM
1 stop4h 25m
Southwest
Deal found 7/8$228
This Priceline deal was found by Cheapflights users on 7/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:00 am
PWM
-
BOS
1 stop5h 25m
JetBlue
Sat 8/154:43 pm
BOS
-
PWM
1 stop7h 42m
JetBlue
Deal found 7/9$237
This Southwest deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:25 am
PWM
-
BOS
1 stop6h 55m
Southwest
Fri 10/305:35 am
BOS
-
PWM
1 stop6h 50m
Southwest
Deal found 7/6$266
This JetBlue deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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.
Wed 8/52:49 pm
PWM
-
BOS
1 stop4h 08m
JetBlue
Wed 8/128:41 am
BOS
-
PWM
1 stop5h 04m
JetBlue
Deal found 7/7$271
This American Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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 8/51:30 pm
PWM
-
BOS
1 stop9h 00m
American Airlines
Wed 8/126:00 am
BOS
-
PWM
1 stop6h 40m
American Airlines
Deal found 7/8$287
This JetBlue deal was found by Cheapflights users on 7/9. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:00 am
PWM
-
BOS
1 stop5h 33m
JetBlue
Mon 8/105:01 am
BOS
-
PWM
1 stop7h 29m
JetBlue
Deal found 7/9$304
This Priceline deal was found by Cheapflights users on 7/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:10 am
PWM
-
BOS
1 stop5h 23m
JetBlue
Wed 8/58:20 pm
BOS
-
PWM
1 stop4h 05m
JetBlue
Deal found 7/9$397
This Expedia deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/26:00 am
PWM
-
BOS
1 stop5h 33m
JetBlue
Sat 8/88:30 pm
BOS
-
PWM
1 stop3h 55m
JetBlue
Deal found 7/6$453
This United Airlines deal was found by Cheapflights users on 7/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/126:00 am
PWM
-
BOS
1 stop6h 43m
United Airlines
Tue 12/157:10 am
BOS
-
PWM
1 stop14h 17m
United Airlines
Deal found 7/9$488

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 July 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$228
(Southwest)

One-way from

$114
(Southwest)
Provider with most accurate pricing for Portland-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Boston Logan Intl flights.
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From Portland to Massachusetts
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One-way flight from Portland to Massachusetts
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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 July 12, 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

Price

Cheapest round-trip
Quickest round-trip

PortlandBoston

PWM - BOS

PWMBOS

Portland

Thu 8/13

5:55 am-9:50 am

1 stop3h 55m

Boston Logan Intl

Sat 8/15

4:35 pm-9:00 pm

1 stop4h 25m

$228

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 8/5

2:49 pm-6:57 pm

1 stop4h 08m

Boston Logan Intl

Wed 8/12

4:30 pm-12:25 am

1 stop7h 55m

$271

PortlandBoston

PWM - BOS

PWMBOS

Portland

Fri 8/7

6:00 am-11:33 am

1 stop5h 33m

Boston Logan Intl

Fri 8/14

8:09 pm-12:25 am

1 stop4h 16m

$271

PortlandBoston

PWM - BOS

PWMBOS

Portland

Tue 8/4

1:25 pm-6:57 pm

1 stop5h 32m

Boston Logan Intl

Tue 8/11

5:01 am-12:21 pm

1 stop7h 20m

$271

PortlandBoston

PWM - BOS

PWMBOS

Portland

Thu 8/13

6:00 am-2:43 pm

1 stop8h 43m

Boston Logan Intl

Sat 8/15

7:05 pm-12:25 am

1 stop5h 20m

$278

PortlandBoston

PWM - BOS

PWMBOS

Portland

Fri 8/7

6:00 am-11:33 am

1 stop5h 33m

Boston Logan Intl

Mon 8/10

5:01 am-12:30 pm

1 stop7h 29m

$304

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 8/1

6:10 am-11:33 am

1 stop5h 23m

Boston Logan Intl

Wed 8/5

8:20 pm-12:25 am

1 stop4h 05m

$397

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 8/1

6:38 pm-7:46 am

2 stops37h 08m

Boston Logan Intl

Wed 8/5

8:41 am-4:16 pm

1 stop7h 35m

$645

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 7/22

2:40 pm-6:59 pm

1 stop4h 19m

Boston Logan Intl

Sun 7/26

7:39 pm-12:16 am

1 stop4h 37m

$655

PortlandBoston

PWM - BOS

PWMBOS

Portland

Fri 7/17

5:35 am-12:10 pm

1 stop6h 35m

Boston Logan Intl

Sat 7/18

6:45 pm-11:45 pm

1 stop5h 00m

$722

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/9

Showing 1-10 of 23 resultsSorted by cheapest first
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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.
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
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 Portland to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Portland to Massachusetts?

    If you book a flight to Massachusetts from Portland, you will be flying from Portland, which is the city’s only airport. Portland (PWM) is located 2.9 mi from the center of Portland.

  • How long is the flight from Portland, Maine to Massachusetts?

    Southwest and JetBlue can get you from Portland, Maine to Massachusetts in just under 3h 55m. Your travel time can differ by up to 13m. The distance from Portland, Maine to Massachusetts is about 95 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from Portland to Massachusetts that include hotel bookings?

    Yes. In addition to deals on Portland to Massachusetts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Massachusetts?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Massachusetts.

  • Can I find deals for business class flights from Portland to Massachusetts?

    Yes. Cheapflights offers flight deals from Portland to Massachusetts by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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