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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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — BOS
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$203
(JetBlue)

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 July 29, 2025.

This JetBlue deal was found by Cheapflights users on 7/29. 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 8/236:10 amPWM - BOS
1 stop6h 52mJetBlue
Tue 8/267:40 pmBOS - PWM
1 stop4h 37mJetBlue
Deal found 7/29$203
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/136:00 amPWM - BOS
1 stop8h 14mDelta
Tue 8/199:59 amBOS - PWM
1 stop14h 49mDelta
Deal found 7/27$343
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/206:23 pmPWM - BOS
1 stop15h 33mUnited Airlines
Mon 9/225:30 amBOS - PWM
2 stops17h 33mUnited Airlines
Deal found 7/28$479
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/79:00 amPWM - BOS
1 stop9h 59mAmerican Airlines
Sun 9/1412:30 pmBOS - PWM
1 stop7h 49mAmerican Airlines
Deal found 7/28$498
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/129:46 amPWM - BOS
2 stops13h 24mMultiple Airlines
Sun 9/142:53 pmBOS - PWM
1 stop18h 13mMultiple Airlines
Deal found 7/28$512

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, 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

Sat 8/23

6:10 am-1:02 pm

1 stop6h 52m

Boston Logan Intl

Tue 8/26

7:40 pm-12:17 am

1 stop4h 37m

$203

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 8/13

6:00 am-2:14 pm

1 stop8h 14m

Boston Logan Intl

Tue 8/19

9:59 am-12:48 am

1 stop14h 49m

$343

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 9/20

6:23 pm-9:56 am

1 stop15h 33m

Boston Logan Intl

Mon 9/22

5:30 am-11:03 pm

2 stops17h 33m

$479

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sun 9/7

9:00 am-6:59 pm

1 stop9h 59m

Boston Logan Intl

Sun 9/14

12:30 pm-8:19 pm

1 stop7h 49m

$498

PortlandBoston

PWM - BOS

PWMBOS

Portland

Fri 9/12

9:46 am-11:10 pm

2 stops13h 24m

Boston Logan Intl

Sun 9/14

2:53 pm-9:06 am

1 stop18h 13m

$512

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 8/23

6:05 am-9:36 am

1 stop3h 31m

$102

PortlandBoston

PWM - BOS

PWMBOS

Portland

Thu 8/7

12:46 pm-10:37 am

1 stop21h 51m

$198

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 8/23

8:07 pm-10:34 pm

2 stops26h 27m

$220

PortlandBoston

PWM - BOS

PWMBOS

Portland

Tue 9/16

3:11 pm-5:34 pm

2 stops26h 23m

$304

PortlandBoston

PWM - BOS

PWMBOS

Portland

Thu 8/7

6:05 am-3:18 pm

2 stops9h 13m

$490

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 11 results
1
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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 July 29, 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.

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated July 29, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and JetBlue from Portland to Massachusetts by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,979 reviews

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,979 reviews
Delta
8.0
Very good
7,979 reviews

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,896 reviews
Delta
8.0
Very good
7,979 reviews

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
JetBlue
7.3
Good
2,913 reviews
Delta
8.0
Very good
7,979 reviews

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,979 reviews

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Sun Country Air
6.9
Okay
333 reviews
Delta
8.0
Very good
7,979 reviews

Comfort

7.9

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • What are the cheapest airlines to fly from Portland, Maine to Massachusetts one-way?

    One-way options have recently been found by users for as low as $102 on JetBlue. Other airlines that offer cheap prices include Sun Country Air from $198 and United Airlines from $304 one-way.

  • 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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