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$102+ 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — BOS
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 11, 2025.

Round-trip from

$223
(Priceline)

One-way from

$102
(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 11, 2025.

This Priceline deal was found by Cheapflights users on 9/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/267:09 amPWM - BOS
1 stop9h 14mJetBlue
Tue 9/305:23 amBOS - PWM
1 stop7h 59mJetBlue
Deal found 9/11$223
This JetBlue deal was found by Cheapflights users on 9/10. 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 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 9/10$248
This Expedia deal was found by Cheapflights users on 9/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/97:09 amPWM - BOS
1 stop9h 20mJetBlue
Thu 10/165:15 pmBOS - PWM
1 stop5h 49mJetBlue
Deal found 9/11$273
This Expedia deal was found by Cheapflights users on 9/10. 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 9/227:09 amPWM - BOS
1 stop4h 36mJetBlue
Wed 9/247:08 amBOS - PWM
1 stop6h 14mJetBlue
Deal found 9/10$358
This Delta deal was found by Cheapflights users on 9/9. 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 9/186:35 amPWM - BOS
1 stop9h 25mDelta
Mon 9/228:50 pmBOS - PWM
1 stop17h 11mDelta
Deal found 9/9$382
This JetBlue deal was found by Cheapflights users on 9/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/102:17 pmPWM - BOS
1 stop4h 13mJetBlue
Fri 10/175:15 pmBOS - PWM
1 stop5h 49mJetBlue
Deal found 9/11$413
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/269:46 amPWM - BOS
1 stop28h 02mMultiple Airlines
Tue 9/303:00 pmBOS - PWM
2 stops19h 46mMultiple Airlines
Deal found 9/11$430
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/93:15 pmPWM - BOS
2 stops44h 11mMultiple Airlines
Thu 10/162:15 pmBOS - PWM
1 stop18h 51mMultiple Airlines
Deal found 9/11$493
This JetBlue deal was found by Cheapflights users on 9/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/122:17 pmPWM - BOS
1 stop4h 21mJetBlue
Fri 9/197:08 amBOS - PWM
1 stop6h 14mJetBlue
Deal found 9/11$578
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Wed 9/176:00 amPWM - BOS
1 stop3h 37mUnited Airlines
Wed 9/173:15 pmBOS - PWM
1 stop23h 11mUnited Airlines
Deal found 9/10$728
This JetBlue deal was found by Cheapflights users on 9/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/142:17 pmPWM - BOS
1 stop4h 21mJetBlue
Tue 9/167:08 amBOS - PWM
1 stop6h 13mJetBlue
Deal found 9/10$763
This United Airlines deal was found by Cheapflights users on 9/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1210:05 amPWM - BOS
1 stop7h 29mUnited Airlines
Fri 9/191:00 pmBOS - PWM
2 stops24h 22mUnited Airlines
Deal found 9/11$780

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 11, 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

Fri 9/26

7:09 am-4:23 pm

1 stop9h 14m

Boston Logan Intl

Tue 9/30

5:23 am-1:22 pm

1 stop7h 59m

$223

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

$248

PortlandBoston

PWM - BOS

PWMBOS

Portland

Thu 10/9

7:09 am-4:29 pm

1 stop9h 20m

Boston Logan Intl

Thu 10/16

5:15 pm-11:04 pm

1 stop5h 49m

$273

PortlandBoston

PWM - BOS

PWMBOS

Portland

Mon 9/22

7:09 am-11:45 am

1 stop4h 36m

Boston Logan Intl

Wed 9/24

7:08 am-1:22 pm

1 stop6h 14m

$358

PortlandBoston

PWM - BOS

PWMBOS

Portland

Fri 10/10

2:17 pm-6:30 pm

1 stop4h 13m

Boston Logan Intl

Fri 10/17

5:15 pm-11:04 pm

1 stop5h 49m

$413

PortlandBoston

PWM - BOS

PWMBOS

Portland

Fri 9/26

9:46 am-1:48 pm

1 stop28h 02m

Boston Logan Intl

Tue 9/30

3:00 pm-10:46 am

2 stops19h 46m

$430

PortlandBoston

PWM - BOS

PWMBOS

Portland

Thu 10/9

3:15 pm-11:26 am

2 stops44h 11m

Boston Logan Intl

Thu 10/16

2:15 pm-9:06 am

1 stop18h 51m

$493

PortlandBoston

PWM - BOS

PWMBOS

Portland

Tue 11/25

6:00 am-5:48 pm

1 stop11h 48m

Boston Logan Intl

Sun 11/30

5:57 pm-12:22 pm

1 stop18h 25m

$954

PortlandBoston

PWM - BOS

PWMBOS

Portland

Mon 9/22

6:00 am-12:41 pm

2 stops6h 41m

Boston Logan Intl

Wed 9/24

7:10 am-1:24 pm

1 stop6h 14m

$1,119

PortlandBoston

PWM - BOS

PWMBOS

Portland

Thu 10/23

7:09 am-11:45 am

1 stop4h 36m

$102

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 21 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 11, 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 9h 14m. 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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