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Massachusetts

$239+ 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 3/19. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — BOS
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This JetBlue deal was found by Cheapflights users on 1/28. 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.
Sat 6/62:18 pm
PWM
-
BOS
1 stop6h 18m
JetBlue
Tue 6/99:25 am
BOS
-
PWM
1 stop3h 58m
JetBlue
Deal found 1/28$353
This JetBlue deal was found by Cheapflights users on 1/26. 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.
Sat 5/302:18 pm
PWM
-
BOS
1 stop6h 18m
JetBlue
Wed 6/33:55 pm
BOS
-
PWM
1 stop7h 41m
JetBlue
Deal found 1/26$369
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Tue 2/246:14 pm
PWM
-
BOS
1 stop19h 41m
Multiple Airlines
Tue 3/34:22 pm
BOS
-
PWM
1 stop17h 55m
Multiple Airlines
Deal found 1/26$399
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Tue 2/243:05 pm
PWM
-
BOS
2 stops19h 31m
United Airlines
Tue 3/32:20 pm
BOS
-
PWM
1 stop24h 03m
United Airlines
Deal found 1/27$411
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 2/2510:57 am
PWM
-
BOS
1 stop11h 04m
Multiple Airlines
Wed 3/45:50 pm
BOS
-
PWM
2 stops40h 59m
Multiple Airlines
Deal found 1/26$456
This American Airlines deal was found by Cheapflights users on 1/26. 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 2/257:00 am
PWM
-
BOS
1 stop8h 14m
American Airlines
Wed 3/45:49 am
BOS
-
PWM
1 stop17h 10m
American Airlines
Deal found 1/26$485
This American Airlines deal was found by Cheapflights users on 1/27. 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 2/246:36 pm
PWM
-
BOS
1 stop28h 47m
American Airlines
Tue 3/31:10 pm
BOS
-
PWM
1 stop9h 49m
American Airlines
Deal found 1/27$514
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/1110:57 am
PWM
-
BOS
1 stop24h 40m
Multiple Airlines
Sun 2/1510:01 am
BOS
-
PWM
1 stop24h 48m
Multiple Airlines
Deal found 1/27$662
This Delta deal was found by Cheapflights users on 1/27. 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.
Sat 4/182:51 pm
PWM
-
BOS
1 stop16h 34m
Delta
Tue 4/218:00 pm
BOS
-
PWM
1 stop14h 52m
Delta
Deal found 1/27$680

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$353
(JetBlue)

One-way from

$239
(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.
Search Deals
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 January 29, 2026.
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

Sat 6/6

2:18 pm-8:36 pm

1 stop6h 18m

Boston Logan Intl

Tue 6/9

6:40 pm-11:36 pm

1 stop4h 56m

$353

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 5/30

2:18 pm-8:36 pm

1 stop6h 18m

Boston Logan Intl

Wed 6/3

3:55 pm-11:36 pm

1 stop7h 41m

$369

PortlandBoston

PWM - BOS

PWMBOS

Portland

Tue 2/24

6:14 pm-1:55 pm

1 stop19h 41m

Boston Logan Intl

Tue 3/3

4:22 pm-10:17 am

1 stop17h 55m

$399

PortlandBoston

PWM - BOS

PWMBOS

Portland

Tue 2/24

3:05 pm-10:36 am

2 stops19h 31m

Boston Logan Intl

Tue 3/3

9:30 am-11:20 pm

2 stops13h 50m

$416

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 2/25

7:00 am-3:14 pm

1 stop8h 14m

Boston Logan Intl

Wed 3/4

5:49 am-10:59 pm

1 stop17h 10m

$485

PortlandBoston

PWM - BOS

PWMBOS

Portland

Tue 2/24

6:36 pm-11:23 pm

1 stop28h 47m

Boston Logan Intl

Tue 3/3

1:10 pm-10:59 pm

1 stop9h 49m

$514

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 2/11

10:57 am-11:37 am

1 stop24h 40m

Boston Logan Intl

Sun 2/15

10:01 am-10:49 am

1 stop24h 48m

$662

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 4/18

2:51 pm-7:25 am

1 stop16h 34m

Boston Logan Intl

Tue 4/21

8:00 pm-10:52 am

1 stop14h 52m

$680

PortlandBoston

PWM - BOS

PWMBOS

Portland

Mon 2/23

6:36 pm-11:23 pm

1 stop28h 47m

Boston Logan Intl

Sat 2/28

8:00 am-10:59 pm

1 stop14h 59m

$683

PortlandBoston

PWM - BOS

PWMBOS

Portland

Thu 3/19

6:19 pm-10:40 am

1 stop16h 21m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 12 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, October is the cheapest month in which you can book a flight from Portland, Maine to Massachusetts (average of $123). Flying from Portland, Maine to Massachusetts in December is currently the most expensive (average of $458). 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.

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 6h 18m. 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, October is the cheapest month in which you can book a flight from Portland, Maine to Massachusetts (average of $123). Flying from Portland, Maine to Massachusetts in December is currently the most expensive (average of $458). 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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