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$230+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — BOS
Dec 25 — Jan 11
Thu 12/25
Thu 1/1
1 adult, Economy
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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 November 25, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/25. 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 12/1011:16 amPWM - BOS
1 stop22h 47mMultiple Airlines
Sun 12/1410:22 amBOS - PWM
1 stop24h 19mMultiple Airlines
Deal found 11/25$257
This Kiwi.com deal was found by Cheapflights users on 11/23. 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 12/86:05 pmPWM - BOS
2 stops29h 51mMultiple Airlines
Fri 12/128:11 pmBOS - PWM
1 stop14h 25mMultiple Airlines
Deal found 11/23$297
This Kiwi.com deal was found by Cheapflights users on 11/23. 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 12/199:46 amPWM - BOS
1 stop24h 15mMultiple Airlines
Mon 12/298:08 amBOS - PWM
2 stops50h 28mMultiple Airlines
Deal found 11/23$458
This American Airlines deal was found by Cheapflights users on 11/23. 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 12/236:41 pmPWM - BOS
1 stop41h 27mAmerican Airlines
Mon 1/51:22 pmBOS - PWM
1 stop26h 09mAmerican Airlines
Deal found 11/23$479
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 12/229:46 amPWM - BOS
1 stop24h 21mMultiple Airlines
Mon 12/298:08 amBOS - PWM
2 stops50h 28mMultiple Airlines
Deal found 11/24$481
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 12/311:16 amPWM - BOS
1 stop22h 47mMultiple Airlines
Thu 12/48:11 pmBOS - PWM
1 stop12h 55mMultiple Airlines
Deal found 11/24$496
This American Airlines deal was found by Cheapflights users on 11/24. 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 12/265:45 amPWM - BOS
1 stop8h 35mAmerican Airlines
Fri 1/26:48 pmBOS - PWM
1 stop23h 28mAmerican Airlines
Deal found 11/24$554
This American Airlines deal was found by Cheapflights users on 11/24. 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 12/206:41 pmPWM - BOS
1 stop25h 45mAmerican Airlines
Sat 12/273:05 pmBOS - PWM
1 stop7h 49mAmerican Airlines
Deal found 11/24$606
This United Airlines deal was found by Cheapflights users on 11/24. 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 12/207:08 pmPWM - BOS
2 stops15h 29mUnited Airlines
Sat 12/275:20 amBOS - PWM
1 stop18h 39mUnited Airlines
Deal found 11/24$613

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 November 25, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$249
(Kiwi.com)

One-way from

$230
(Kiwi.com)
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 November 25, 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

Mon 1/19

9:47 am-2:38 pm

1 stop28h 51m

Boston Logan Intl

Fri 1/23

3:43 pm-10:22 am

1 stop18h 39m

$249

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 12/10

11:16 am-10:03 am

1 stop22h 47m

Boston Logan Intl

Sun 12/14

10:22 am-10:41 am

1 stop24h 19m

$257

PortlandBoston

PWM - BOS

PWMBOS

Portland

Mon 12/8

6:05 pm-11:56 pm

2 stops29h 51m

Boston Logan Intl

Fri 12/12

8:11 pm-10:36 am

1 stop14h 25m

$297

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sun 1/18

11:01 am-7:52 am

2 stops20h 51m

Boston Logan Intl

Fri 1/23

3:43 pm-10:22 am

1 stop18h 39m

$316

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 1/7

2:35 pm-7:33 am

1 stop16h 58m

Boston Logan Intl

Sat 1/10

6:00 am-1:45 pm

1 stop7h 45m

$325

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sun 1/11

11:01 am-10:03 am

2 stops23h 02m

$248

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sun 1/4

10:19 am-10:37 am

1 stop24h 18m

$308

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sun 1/11

9:40 am-6:57 pm

1 stop9h 17m

$328

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sun 1/18

3:42 pm-10:36 am

2 stops18h 54m

$459

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sun 1/4

10:49 am-10:01 am

3 stops47h 12m

$524

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

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 $89). Flying from Portland, Maine to Massachusetts in December is currently the most expensive (average of $401). 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 November 25, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 45% on flights from Portland, Maine to Massachusetts by exploring options for tickets in the evening.

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.

  • 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 $89). Flying from Portland, Maine to Massachusetts in December is currently the most expensive (average of $401). 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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