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$122+ 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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — BOS
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Portland to Massachusetts

Keep the following information in mind while searching for Portland to Massachusetts flight deals. Data was last updated September 16, 2025.

Round-trip from

$203
(JetBlue)

One-way from

$122
(Priceline)
From Portland to Massachusetts
Search Deals
One-way flight from Portland to Massachusetts
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Find 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 September 16, 2025.

This JetBlue deal was found by Cheapflights users on 9/15. 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 10/162:17 pmPWM - BOS
1 stop4h 16mJetBlue
Wed 10/225:15 pmBOS - PWM
1 stop5h 49mJetBlue
Deal found 9/15$203
This JetBlue deal was found by Cheapflights users on 9/15. 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.
Tue 9/307:09 amPWM - BOS
1 stop4h 36mJetBlue
Sat 10/45:20 pmBOS - PWM
1 stop4h 42mJetBlue
Deal found 9/15$218
This Priceline deal was found by Cheapflights users on 9/16. 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.
Wed 10/12:17 pmPWM - BOS
1 stop7h 12mJetBlue
Sun 10/56:10 amBOS - PWM
1 stop7h 12mJetBlue
Deal found 9/16$223
This Priceline deal was found by Cheapflights users on 9/16. 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 10/162:17 pmPWM - BOS
1 stop4h 16mJetBlue
Thu 10/235:15 pmBOS - PWM
1 stop5h 49mJetBlue
Deal found 9/16$228
This JetBlue deal was found by Cheapflights users on 9/16. 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.
Tue 10/77:30 amPWM - BOS
1 stop6h 20mJetBlue
Tue 10/145:15 pmBOS - PWM
1 stop5h 49mJetBlue
Deal found 9/16$253
This Trip.com deal was found by Cheapflights users on 9/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/137:09 amPWM - BOS
1 stop4h 36mJetBlue
Mon 10/207:00 amBOS - PWM
1 stop6h 22mJetBlue
Deal found 9/15$328
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/163:15 pmPWM - BOS
2 stops20h 11mMultiple Airlines
Thu 10/232:15 pmBOS - PWM
1 stop18h 51mMultiple Airlines
Deal found 9/16$381
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 9/206:18 pmPWM - BOS
1 stop15h 00mMultiple Airlines
Sun 9/2112:59 pmBOS - PWM
2 stops20h 07mMultiple Airlines
Deal found 9/14$391
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/16:18 pmPWM - BOS
1 stop15h 00mMultiple Airlines
Sun 10/58:47 amBOS - PWM
2 stops24h 19mMultiple Airlines
Deal found 9/16$409
This lol.travel deal was found by Cheapflights users on 9/15. 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.
Thu 10/168:00 amPWM - BOS
1 stop7h 13mUnited Airlines
Wed 10/225:30 amBOS - PWM
2 stops8h 23mUnited Airlines
Deal found 9/15$517
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/139:46 amPWM - BOS
1 stop27h 34mMultiple Airlines
Mon 10/209:18 amBOS - PWM
2 stops49h 23mMultiple Airlines
Deal found 9/15$521

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 September 16, 2025.
Use the filters below to find and compare flights from Portland to Massachusetts that are best for you.

Fly from

Portland

Fly to

Massachusetts

Route

Depart

Return

Price

PortlandBoston

PWM - BOS

PWMBOS

Portland

Thu 10/16

2:17 pm-6:33 pm

1 stop4h 16m

Boston Logan Intl

Wed 10/22

5:15 pm-11:04 pm

1 stop5h 49m

$203

PortlandBoston

PWM - BOS

PWMBOS

Portland

Fri 10/17

7:09 am-1:50 pm

1 stop6h 41m

Boston Logan Intl

Mon 10/20

7:00 am-1:22 pm

1 stop6h 22m

$203

PortlandBoston

PWM - BOS

PWMBOS

Portland

Tue 9/30

7:09 am-11:45 am

1 stop4h 36m

Boston Logan Intl

Sat 10/4

5:20 pm-10:02 pm

1 stop4h 42m

$218

PortlandBoston

PWM - BOS

PWMBOS

Portland

Thu 10/16

2:17 pm-6:33 pm

1 stop4h 16m

Boston Logan Intl

Thu 10/23

5:15 pm-11:04 pm

1 stop5h 49m

$228

PortlandBoston

PWM - BOS

PWMBOS

Portland

Tue 10/7

7:30 am-1:50 pm

1 stop6h 20m

Boston Logan Intl

Tue 10/14

5:15 pm-11:04 pm

1 stop5h 49m

$253

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 10/1

6:18 pm-9:18 am

1 stop15h 00m

Boston Logan Intl

Sun 10/5

8:47 am-9:06 am

2 stops24h 19m

$409

PortlandBoston

PWM - BOS

PWMBOS

Portland

Thu 10/16

8:00 am-3:13 pm

1 stop7h 13m

Boston Logan Intl

Wed 10/22

5:30 am-1:53 pm

2 stops8h 23m

$517

PortlandBoston

PWM - BOS

PWMBOS

Portland

Mon 10/13

9:46 am-1:20 pm

1 stop27h 34m

Boston Logan Intl

Mon 10/20

9:18 am-10:41 am

2 stops49h 23m

$521

PortlandBoston

PWM - BOS

PWMBOS

Portland

Thu 10/2

12:33 pm-11:07 am

1 stop22h 34m

Boston Logan Intl

Sat 10/4

3:00 pm-2:30 pm

2 stops23h 30m

$559

PortlandBoston

PWM - BOS

PWMBOS

Portland

Thu 10/2

7:09 am-1:45 pm

1 stop6h 36m

$122

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 18 results
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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

What is the cheapest month to book a flight from Portland, Maine to Massachusetts?

Currently, January is the cheapest month in which you can book a flight from Portland, Maine to Massachusetts (average of $218). Flying from Portland, Maine to Massachusetts in July is currently the most expensive (average of $311). 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 PWM 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 September 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Portland, Maine to Massachusetts as you normally would.

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?

    JetBlue can get you from Portland, Maine to Massachusetts in just under 4h 16m. Your travel time can differ by up to . The distance from Portland, Maine to Massachusetts is about 95 mi.

  • 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.

  • What is the cheapest month to book a flight from Portland, Maine to Massachusetts?

    Currently, January is the cheapest month in which you can book a flight from Portland, Maine to Massachusetts (average of $218). Flying from Portland, Maine to Massachusetts in July is currently the most expensive (average of $311). 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.

See more FAQs

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