HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Massachusetts

$238+ 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 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — BOS
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Massachusetts with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$247
(Kiwi.com)

One-way from

$238
(American Airlines)
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

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 January 8, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/7. 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 2/29:47 amPWM - BOS
1 stop13h 32mMultiple Airlines
Thu 2/53:43 pmBOS - PWM
1 stop17h 24mMultiple Airlines
Deal found 1/7$247
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 1/2311:29 amPWM - BOS
2 stops27h 09mMultiple Airlines
Tue 1/273:43 pmBOS - PWM
1 stop18h 39mMultiple Airlines
Deal found 1/7$260
This American Airlines deal was found by Cheapflights users on 1/7. 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 9/261:02 pmPWM - BOS
1 stop8h 43mAmerican Airlines
Wed 9/3012:30 pmBOS - PWM
1 stop7h 53mAmerican Airlines
Deal found 1/7$309
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 1/2811:02 amPWM - BOS
1 stop12h 17mMultiple Airlines
Sat 2/76:39 pmBOS - PWM
2 stops38h 28mMultiple Airlines
Deal found 1/7$328
This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
Sat 1/3111:02 amPWM - BOS
1 stop12h 17mMultiple Airlines
Sat 2/76:39 pmBOS - PWM
2 stops38h 28mMultiple Airlines
Deal found 1/7$367
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 2/410:57 amPWM - BOS
1 stop27h 41mMultiple Airlines
Wed 2/115:53 pmBOS - PWM
2 stops40h 56mMultiple Airlines
Deal found 1/6$383
This American Airlines deal was found by Cheapflights users on 1/7. 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 7/36:00 amPWM - BOS
1 stop15h 29mAmerican Airlines
Tue 7/77:31 pmBOS - PWM
1 stop17h 10mAmerican Airlines
Deal found 1/7$411
This United Airlines deal was found by Cheapflights users on 1/7. 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 1/242:31 pmPWM - BOS
1 stop9h 18mUnited Airlines
Mon 1/265:45 amBOS - PWM
1 stop8h 46mUnited Airlines
Deal found 1/7$461
This United Airlines deal was found by Cheapflights users on 1/8. 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 2/44:10 pmPWM - BOS
1 stop20h 36mUnited Airlines
Thu 4/26:00 amBOS - PWM
1 stop15h 40mUnited Airlines
Deal found 1/8$478

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 8, 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

Mon 2/2

9:47 am-11:19 pm

1 stop13h 32m

Boston Logan Intl

Thu 2/5

3:43 pm-9:07 am

1 stop17h 24m

$247

PortlandBoston

PWM - BOS

PWMBOS

Portland

Fri 1/23

11:29 am-2:38 pm

2 stops27h 09m

Boston Logan Intl

Tue 1/27

3:43 pm-10:22 am

1 stop18h 39m

$260

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 1/28

11:02 am-11:19 pm

1 stop12h 17m

Boston Logan Intl

Sat 2/7

6:39 pm-9:07 am

2 stops38h 28m

$328

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 1/31

11:02 am-11:19 pm

1 stop12h 17m

Boston Logan Intl

Sat 2/7

6:39 pm-9:07 am

2 stops38h 28m

$367

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 2/4

10:57 am-2:38 pm

1 stop27h 41m

Boston Logan Intl

Wed 2/11

5:53 pm-10:49 am

2 stops40h 56m

$383

PortlandBoston

PWM - BOS

PWMBOS

Portland

Fri 7/3

6:00 am-9:29 pm

1 stop15h 29m

Boston Logan Intl

Tue 7/7

7:31 pm-12:41 pm

1 stop17h 10m

$411

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 1/24

2:31 pm-11:49 pm

1 stop9h 18m

Boston Logan Intl

Mon 1/26

5:45 am-2:31 pm

1 stop8h 46m

$461

PortlandBoston

PWM - BOS

PWMBOS

Portland

Wed 2/4

4:10 pm-12:46 pm

1 stop20h 36m

Boston Logan Intl

Thu 4/2

6:00 am-9:40 pm

1 stop15h 40m

$478

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sat 2/14

6:49 pm-10:29 am

1 stop15h 40m

$238

PortlandBoston

PWM - BOS

PWMBOS

Portland

Sun 1/25

11:01 am-4:19 pm

3 stops29h 18m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Showing 1-10 of 14 results
1
2

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.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
Boston to Tampa flights
Boston to Fort Lauderdale flights
Boston to Miami flights
Boston to Orlando flights
Boston to Los Angeles flights
Boston to Fort Myers flights
Boston to Dallas/Fort Worth flights
Boston to West Palm Beach flights
Boston to Las Vegas flights
Boston to Sky Harbor Intl flights
Boston to Denver flights
Boston to Sarasota flights
Boston to Salt Lake City flights
Boston to Atlanta flights
Boston to Baltimore flights
Boston to New Orleans flights
Boston to Hobby flights
Boston to Seattle flights
Boston to O'Hare Intl flights
Boston to Dulles Intl flights
Boston to Reagan-National flights
Boston to George Bush Intcntl flights
Boston to Austin flights
Boston to San Diego flights
Boston to Newark flights
Boston to Charleston flights
Boston to Charlotte flights
Boston to LaGuardia flights
Boston to San Francisco flights
Boston to Raleigh flights
Boston to Key West flights
Boston to Jacksonville flights
Boston to John F Kennedy Intl flights
Boston to Nashville flights
Boston to Savannah flights
Boston to Myrtle Beach flights
Boston to Philadelphia flights
Boston to Ontario flights
Boston to Honolulu flights
Boston to Detroit flights
Boston to Daytona Beach flights
Boston to Midway flights
Boston to Love Field flights
Boston to Minneapolis flights
Boston to Bozeman flights
Boston to Cincinnati flights
Portland to Orlando flights
Boston to Portland flights
Boston to Pittsburgh flights
Boston to San Antonio flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.