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$124+ 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 8/22. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — BOS
Aug 28 — Sep 41
Fri 8/28
Fri 9/4
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 29, 2026.

This JetBlue deal was found by Cheapflights users on 7/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/11:20 pm
PWM
-
BOS
1 stop4h 32m
JetBlue
Sat 9/58:41 am
BOS
-
PWM
1 stop5h 04m
JetBlue
Deal found 7/27$247
This Priceline deal was found by Cheapflights users on 7/25. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:41 am
PWM
-
BOS
1 stop7h 43m
JetBlue
Thu 9/37:05 pm
BOS
-
PWM
1 stop5h 20m
JetBlue
Deal found 7/25$281
This Priceline deal was found by Cheapflights users on 7/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/272:40 pm
PWM
-
BOS
1 stop4h 17m
JetBlue
Thu 9/37:05 pm
BOS
-
PWM
1 stop5h 20m
JetBlue
Deal found 7/26$314
This Justfly.com deal was found by Cheapflights users on 7/26. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:00 am
PWM
-
BOS
1 stop14h 49m
JetBlue
Sun 9/134:11 pm
BOS
-
PWM
1 stop7h 43m
JetBlue
Deal found 7/26$338
This Priceline deal was found by Cheapflights users on 7/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:00 am
PWM
-
BOS
1 stop8h 43m
JetBlue
Mon 8/318:41 am
BOS
-
PWM
1 stop5h 04m
JetBlue
Deal found 7/27$342
This Priceline deal was found by Cheapflights users on 7/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:00 am
PWM
-
BOS
1 stop5h 33m
JetBlue
Sat 8/294:43 pm
BOS
-
PWM
1 stop7h 42m
JetBlue
Deal found 7/28$358
This Southwest deal was found by Cheapflights users on 7/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/247:40 am
PWM
-
BOS
1 stop7h 15m
Southwest
Mon 8/319:40 am
BOS
-
PWM
1 stop5h 20m
Southwest
Deal found 7/27$377
This Priceline deal was found by Cheapflights users on 7/24. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:41 am
PWM
-
BOS
1 stop7h 43m
JetBlue
Wed 8/127:04 pm
BOS
-
PWM
1 stop5h 21m
JetBlue
Deal found 7/24$381
This Kiwi.com deal was found by Cheapflights users on 7/24. 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.
Fri 8/217:00 am
PWM
-
BOS
2 stops28h 47m
Multiple Airlines
Fri 8/2812:45 pm
BOS
-
PWM
1 stop27h 31m
Multiple Airlines
Deal found 7/24$430
This Southwest deal was found by Cheapflights users on 7/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/110:30 am
PWM
-
BOS
1 stop3h 55m
Southwest
Tue 12/13:35 pm
BOS
-
PWM
1 stop6h 10m
Southwest
Deal found 7/25$439

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 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$247
(JetBlue)

One-way from

$124
(Priceline)
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
Search Deals
One-way flight from Portland to Massachusetts
Search Deals

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 29, 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

PortlandBoston

PWM - BOS

PWMBOS

Portland

Tue 9/1

1:20 pm-5:52 pm

1 stop4h 32m

Boston Logan Intl

Sat 9/5

8:41 am-1:45 pm

1 stop5h 04m

$247

PortlandBoston

PWM - BOS

PWMBOS

Portland

Fri 9/25

6:00 am-10:51 am

1 stop4h 51m

Boston Logan Intl

Tue 9/29

6:40 pm-11:54 pm

1 stop5h 14m

$247

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 8/15

6:41 am-2:24 pm

1 stop7h 43m

Boston Logan Intl

Thu 9/3

7:05 pm-12:25 am

1 stop5h 20m

$281

PortlandBoston

PWM - BOS

PWMBOS

Portland

Thu 8/27

6:00 am-11:25 am

1 stop5h 25m

Boston Logan Intl

Thu 9/3

7:05 pm-12:25 am

1 stop5h 20m

$314

PortlandBoston

PWM - BOS

PWMBOS

Portland

Fri 9/11

6:00 am-8:49 pm

1 stop14h 49m

Boston Logan Intl

Sun 9/13

4:11 pm-11:54 pm

1 stop7h 43m

$338

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 9/16

6:00 am-2:27 pm

1 stop8h 27m

Boston Logan Intl

Wed 9/30

4:11 pm-11:54 pm

1 stop7h 43m

$342
Quickest round-trip

PortlandBoston

PWM - BOS

PWMBOS

Portland

Mon 8/24

2:40 pm-6:27 pm

1 stop3h 47m

Boston Logan Intl

Mon 8/31

8:41 am-1:45 pm

1 stop5h 04m

$358

PortlandBoston

PWM - BOS

PWMBOS

Portland

Mon 8/24

7:40 am-2:55 pm

1 stop7h 15m

Boston Logan Intl

Mon 8/31

9:40 am-3:00 pm

1 stop5h 20m

$377
Cheapest one-way

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 8/22

2:40 pm-6:57 pm

1 stop4h 17m

$124

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 9/16

6:00 am-10:51 am

1 stop4h 51m

$124

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/25

Showing 1-10 of 20 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?

    JetBlue can get you from Portland, Maine to Massachusetts in just under 4h 32m. 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.

See more FAQs

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