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Cheap flights from Massachusetts to Portland from $102

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Massachusetts to Portland departing on 9/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

JetBlue Logo
7:35 pm - 12:17 amBOS-PWM
4h 42m1 stop
JetBlue Logo
2:17 pm - 6:33 pmPWM-BOS
4h 16m1 stop
$203JetBlue
Find Deal
Sat, Aug 30 - Sat, Sep 6
JetBlue Logo
5:20 pm - 10:02 pmBOS-PWM
4h 42m1 stop
JetBlue Logo
2:17 pm - 9:00 pmPWM-BOS
6h 43m1 stop
$206JetBlue
Find Deal
Thu, Sep 4 - Thu, Sep 11
JetBlue Logo
5:19 pm - 10:07 pmBOS-PWM
4h 48m1 stop
JetBlue Logo
7:09 am - 11:45 amPWM-BOS
4h 36m1 stop
$228JetBlue
Find Deal
Fri, Sep 19 - Mon, Sep 22
Southwest Logo
6:00 am - 9:50 amBDL-PWM
3h 50m1 stop
Southwest Logo
11:45 am - 6:15 pmPWM-BDL
6h 30m1 stop
$256Southwest
Find Deal
Tue, Sep 30 - Thu, Oct 2
Southwest Logo
1:55 pm - 11:20 pmBDL-PWM
9h 25m1 stop
Southwest Logo
5:40 pm - 11:15 pmPWM-BDL
5h 35m1 stop
$261Southwest
Find Deal
Fri, Sep 5 - Fri, Sep 12
American Airlines Logo
2:49 pm - 11:44 pmBDL-PWM
8h 55m1 stop
American Airlines Logo
6:00 am - 4:34 pmPWM-BDL
10h 34m1 stop
$317American Airlines
Find Deal
Wed, Aug 27 - Sat, Aug 30
Delta Logo
5:50 am - 11:10 amALB-PWM
5h 20m1 stop
Delta Logo
4:50 pm - 11:08 pmPWM-ALB
6h 18m1 stop
$321Delta
Find Deal
Wed, Aug 20 - Tue, Aug 26
American Airlines Logo
12:30 pm - 8:11 pmBOS-PWM
7h 41m1 stop
American Airlines Logo
7:05 am - 6:59 pmPWM-BOS
11h 54m1 stop
$333American Airlines
Find Deal
Thu, Sep 4 - Thu, Sep 11
Logo
6:10 am - 2:32 pmBOS-PWM
32h 22m2 stops
Logo
2:21 pm - 12:04 pmPWM-BOS
21h 43m1 stop
$361
Find Deal
Sat, Aug 30 - Sat, Sep 6
Logo
6:55 pm - 8:12 pmBOS-PWM
25h 17m2 stops
Logo
6:18 pm - 11:13 amPWM-BOS
16h 55m2 stops
$417
Find Deal
Sat, Aug 30 - Sat, Sep 6

Southwest flights from Massachusetts to Portland, Maine

Our best Southwest deals on Massachusetts to Portland, Maine flight tickets
Southwest
Sep 30
BDL6:00 amHartford Bradley Intl
3h 50m
1 stop
PWM9:50 amPortland
Oct 2
PWM11:45 amPortland
6h 30m
1 stop
BDL6:15 pmHartford Bradley Intl
$256
Find similar
Southwest
Sep 5
BDL1:55 pmHartford Bradley Intl
9h 25m
1 stop
PWM11:20 pmPortland
Sep 12
PWM5:40 pmPortland
5h 35m
1 stop
BDL11:15 pmHartford Bradley Intl
$261
Find similar
Southwest
Aug 31
BDL6:15 amHartford Bradley Intl
10h 50m
2 stops
PWM5:05 pmPortland
Sep 4
PWM5:40 pmPortland
5h 35m
1 stop
BDL11:15 pmHartford Bradley Intl
$263
Find similar

JetBlue flights from Massachusetts to Portland, Maine

Our best JetBlue deals on Massachusetts to Portland, Maine flight tickets
JetBlue
Aug 30
BOS7:35 pmBoston Logan Intl
4h 42m
1 stop
PWM12:17 amPortland
Sep 6
PWM2:17 pmPortland
4h 16m
1 stop
BOS6:33 pmBoston Logan Intl
$203
Find similar
JetBlue
Sep 4
BOS5:20 pmBoston Logan Intl
4h 42m
1 stop
PWM10:02 pmPortland
Sep 11
PWM2:17 pmPortland
6h 43m
1 stop
BOS9:00 pmBoston Logan Intl
$206
Find similar
JetBlue
Sep 19
BOS5:19 pmBoston Logan Intl
4h 48m
1 stop
PWM10:07 pmPortland
Sep 22
PWM7:09 amPortland
4h 36m
1 stop
BOS11:45 amBoston Logan Intl
$228
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Massachusetts to Portland, Maine 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, momondo users made 832,500 searches. Data last updated August 7, 2025.
Use the filters below to find and compare flights from Massachusetts to Portland, Maine that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Sat 8/30

7:35 pm-12:17 am

1 stop4h 42m

Portland

Sat 9/6

2:17 pm-6:33 pm

1 stop4h 16m

$203

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Thu 9/4

5:20 pm-10:02 pm

1 stop4h 42m

Portland

Thu 9/11

2:17 pm-9:00 pm

1 stop6h 43m

$206

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Fri 9/19

5:19 pm-10:07 pm

1 stop4h 48m

Portland

Mon 9/22

7:09 am-11:45 am

1 stop4h 36m

$228

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Tue 9/30

6:00 am-9:50 am

1 stop3h 50m

Portland

Thu 10/2

11:45 am-6:15 pm

1 stop6h 30m

$256

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Fri 9/5

1:55 pm-11:20 pm

1 stop9h 25m

Portland

Fri 9/12

5:40 pm-11:15 pm

1 stop5h 35m

$261

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Wed 8/27

2:49 pm-11:44 pm

1 stop8h 55m

Portland

Sat 8/30

6:00 am-4:34 pm

1 stop10h 34m

$317

AlbanyPortland

ALB - PWM

ALBPWM

Albany Intl

Wed 8/20

5:50 am-11:10 am

1 stop5h 20m

Portland

Tue 8/26

4:50 pm-11:08 pm

1 stop6h 18m

$321

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Thu 9/4

12:30 pm-8:11 pm

1 stop7h 41m

Portland

Thu 9/11

7:05 am-6:59 pm

1 stop11h 54m

$333

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Sat 8/30

6:10 am-2:32 pm

2 stops32h 22m

Portland

Sat 9/6

2:21 pm-12:04 pm

1 stop21h 43m

$361

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Sat 8/30

6:55 pm-8:12 pm

2 stops25h 17m

Portland

Sat 9/6

6:18 pm-11:13 am

2 stops16h 55m

$417

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Portland from

How to get the cheapest flight ticket from Massachusetts to Portland, Maine

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Portland, Maine?

On average, the least expensive day to fly to Portland, Maine from Massachusetts is on a Wednesday. momondo users have found tickets for Wednesday departures for as low as $175. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Thursday is the most expensive day to depart from Massachusetts because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $394.

What is the cheapest time of day to depart on your flight to Portland, Maine?

In the afternoon is the cheapest time of day to fly from Massachusetts to Portland, Maine when you can find flight prices for as low as $210. Flying to Portland, Maine in the afternoon is an ideal time because this is during off-peak travel hours. Try not to purchase tickets in the morning because they tend to be around $236. Of course, these prices can vary depending on the time of year and what airport you fly to.

Cheap Massachusetts to Portland, Maine flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Massachusetts to Portland, Maine

Best Price Found

$102

Fastest flight time

3h 50m

Direct flights

None

Airports in Portland, Maine

1 airport
The best one-way flight to Portland, Maine from Massachusetts in the past 72 hours is $102. The best round-trip flight deal from Massachusetts to Portland, Maine found on momondo in the last 72 hours is $203.
The fastest flight from Massachusetts to Portland, Maine takes 3h 50m
There are no direct flights from Massachusetts to Portland, Maine. Popular non-direct routes for this connection are Albany Intl Airport - Portland Airport, Boston Logan Intl Airport - Portland Airport and Hartford Bradley Intl Airport - Portland Airport.
There is 1 airport near Portland, Maine: Portland (PWM)
Search flight deals

  • When did momondo last update prices for flights from Massachusetts to Portland Airport?

    Prices for flights from Massachusetts to Portland Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Massachusetts to Portland Airport?

  • How old do you have to be to fly from Massachusetts to Portland Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Massachusetts to Portland Airport.

  • What documentation or ID do you need to fly to Portland Airport?

    The necessary travel and health documents for your Portland Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Massachusetts to Portland, Maine

Compare and see reviews for airlines that fly from Massachusetts to Portland, Maine with momondo
Airline
Rating
Free Cancellation
Price
JetBluePriceFrom $151Free CancellationRating
7.2
2,915 reviews
Search JetBlue flights

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Boothbay Harbor
Jackson
Conway
Freeport
Bartlett
Lewiston
Gorham
Brunswick
Auburn
Intervale
Windham
Bath
Falmouth
Georgetown
Oxford
Tamworth

Why use momondo?

Why should I use momondo to find a flight deal from Massachusetts to Portland?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Massachusetts to Portland. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Massachusetts to Portland with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Portland from Massachusetts with this policy.

How can momondo help me find flights from Massachusetts to Portland?

momondo provides multiple filters to help you find the best flight to Portland from Massachusetts. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Massachusetts to Portland right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Portland from Massachusetts. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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