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Cheap flights from Massachusetts to Portland from $107

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 5/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Massachusetts to Portland

Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
5:02 pm - 11:03 pm
BOS
-
PWM
6h 01m
1 stop
JetBlue Logo
7:20 am - 2:28 pm
PWM
-
BOS
7h 08m
1 stop
$223JetBlue
Fri, May 8 - Tue, May 12
JetBlue Logo
3:08 pm - 11:03 pm
BOS
-
PWM
7h 55m
1 stop
JetBlue Logo
7:20 am - 2:28 pm
PWM
-
BOS
7h 08m
1 stop
$225JetBlue
Tue, May 12 - Sat, May 16
Multiple Airlines Logo
9:29 am - 4:16 pm
BOS
-
PWM
6h 47m
1 stop
Multiple Airlines Logo
3:16 pm - 11:06 am
PWM
-
BOS
19h 50m
2 stops
$281Multiple Airlines
Wed, May 13 - Tue, May 19
Multiple Airlines Logo
9:29 am - 4:16 pm
BOS
-
PWM
6h 47m
1 stop
Multiple Airlines Logo
5:01 pm - 9:12 am
PWM
-
BOS
16h 11m
2 stops
$306Multiple Airlines
Wed, May 13 - Sat, May 16
Southwest Logo
6:00 am - 12:25 pm
BDL
-
PWM
6h 25m
1 stop
Southwest Logo
7:40 am - 4:10 pm
PWM
-
BDL
8h 30m
1 stop
$347Southwest
Tue, Aug 18 - Fri, Aug 21
United Airlines Logo
7:30 pm - 11:51 pm
ALB
-
PWM
4h 21m
1 stop
United Airlines Logo
5:15 am - 10:11 am
PWM
-
ALB
4h 56m
1 stop
$347United Airlines
Sat, Jun 13 - Mon, Jun 15
Southwest Logo
11:20 am - 9:30 pm
BDL
-
PWM
10h 10m
1 stop
Southwest Logo
2:50 pm - 9:10 pm
PWM
-
BDL
6h 20m
1 stop
$352Southwest
Sun, Sep 13 - Wed, Sep 16
Delta Logo
5:55 am - 10:23 am
ALB
-
PWM
4h 28m
1 stop
Delta Logo
5:15 pm - 11:03 pm
PWM
-
ALB
5h 48m
1 stop
$367Delta
Fri, May 8 - Mon, May 11
Delta Logo
5:55 am - 10:23 am
ALB
-
PWM
4h 28m
1 stop
Delta Logo
5:15 pm - 11:03 pm
PWM
-
ALB
5h 48m
1 stop
$387Delta
Fri, May 8 - Mon, May 11
United Airlines Logo
7:30 pm - 11:51 pm
ALB
-
PWM
4h 21m
1 stop
United Airlines Logo
7:16 pm - 11:47 pm
PWM
-
ALB
4h 31m
1 stop
$417United Airlines
Tue, May 26 - Wed, May 27

JetBlue flights from Massachusetts to Portland, Maine

Our best JetBlue deals on Massachusetts to Portland, Maine flight tickets
JetBlue
May 8
BOS5:02 pmBoston Logan Intl
6h 01m
1 stop
PWM11:03 pmPortland
May 12
PWM7:20 amPortland
7h 08m
1 stop
BOS2:28 pmBoston Logan Intl
$223
JetBlue
May 12
BOS3:08 pmBoston Logan Intl
7h 55m
1 stop
PWM11:03 pmPortland
May 16
PWM7:20 amPortland
7h 08m
1 stop
BOS2:28 pmBoston Logan Intl
$225
JetBlue
May 12
BOS3:08 pmBoston Logan Intl
7h 55m
1 stop
PWM11:03 pmPortland
May 16
PWM7:20 amPortland
7h 08m
1 stop
BOS2:28 pmBoston Logan Intl
$227

Southwest flights from Massachusetts to Portland, Maine

Our best Southwest deals on Massachusetts to Portland, Maine flight tickets
Southwest
Aug 18
BDL6:00 amHartford Bradley Intl
6h 25m
1 stop
PWM12:25 pmPortland
Aug 21
PWM7:40 amPortland
8h 30m
1 stop
BDL4:10 pmHartford Bradley Intl
$347
Southwest
Sep 13
BDL11:20 amHartford Bradley Intl
10h 10m
1 stop
PWM9:30 pmPortland
Sep 16
PWM2:50 pmPortland
6h 20m
1 stop
BDL9:10 pmHartford Bradley Intl
$352
Southwest
May 9
BDL4:55 pmHartford Bradley Intl
6h 15m
1 stop
PWM11:10 pmPortland
May 16
PWM5:40 amPortland
8h 40m
1 stop
BDL2:20 pmHartford Bradley Intl
$372

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 April 15, 2026.
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

Cheapest round-trip

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Fri 5/8

5:02 pm-11:03 pm

1 stop6h 01m

Portland

Tue 5/12

7:20 am-2:28 pm

1 stop7h 08m

$223

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Tue 5/12

3:08 pm-11:03 pm

1 stop7h 55m

Portland

Sat 5/16

7:20 am-2:28 pm

1 stop7h 08m

$225

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Wed 5/13

9:29 am-4:16 pm

1 stop6h 47m

Portland

Tue 5/19

3:16 pm-11:06 am

2 stops19h 50m

$281

BostonPortland

BOS - PWM

BOSPWM

Boston Logan Intl

Wed 5/13

9:29 am-4:16 pm

1 stop6h 47m

Portland

Sat 5/16

5:01 pm-9:12 am

2 stops16h 11m

$306

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Tue 8/18

6:00 am-12:25 pm

1 stop6h 25m

Portland

Fri 8/21

7:40 am-4:10 pm

1 stop8h 30m

$347

AlbanyPortland

ALB - PWM

ALBPWM

Albany Intl

Sat 6/13

7:30 pm-11:51 pm

1 stop4h 21m

Portland

Mon 6/15

5:15 am-10:11 am

1 stop4h 56m

$347

HartfordPortland

BDL - PWM

BDLPWM

Hartford Bradley Intl

Sun 9/13

11:20 am-9:30 pm

1 stop10h 10m

Portland

Wed 9/16

2:50 pm-9:10 pm

1 stop6h 20m

$352

AlbanyPortland

ALB - PWM

ALBPWM

Albany Intl

Fri 5/8

5:55 am-10:23 am

1 stop4h 28m

Portland

Mon 5/11

5:15 pm-11:03 pm

1 stop5h 48m

$367

AlbanyPortland

ALB - PWM

ALBPWM

Albany Intl

Fri 5/8

5:55 am-10:23 am

1 stop4h 28m

Portland

Mon 5/11

5:15 pm-11:03 pm

1 stop5h 48m

$387
Quickest round-trip

AlbanyPortland

ALB - PWM

ALBPWM

Albany Intl

Tue 5/26

7:30 pm-11:51 pm

1 stop4h 21m

Portland

Wed 5/27

7:16 pm-11:47 pm

1 stop4h 31m

$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 airline that flies from Massachusetts to Portland?

JetBlue, Breeze Airways, and American Airlines are the most popular carriers operating from Massachusetts to Portland

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

Fastest flight time

3h 40m

Direct flights

None
The fastest flight from Massachusetts to Portland, Maine takes 3h 40m
There are no direct flights from Massachusetts to Portland, Maine. There are no popular flight routes from Massachusetts to Portland, Maine.
Search flight deals

Frequently asked questions about flying from Massachusetts to Portland, Maine

  • 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 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.

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
Lewiston
Brunswick
Bartlett
Gorham
Auburn
Windham
Intervale
Bath
Oxford
Georgetown
Falmouth
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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Fri 5/15
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