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Cheap flights from Milwaukee to Boston from $171

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Milwaukee to Boston departing on 2/19. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
5:39 pm - 11:27 pm
MKE
-
PWM
4h 48m1 stop
United Airlines Logo
4:10 pm - 9:59 pm
PWM
-
MKE
6h 49m1 stop
$293United Airlines
Tue, Jan 13 - Tue, Jan 20
United Airlines Logo
5:00 am - 2:31 pm
MKE
-
PWM
8h 31m2 stops
United Airlines Logo
4:10 pm - 9:59 pm
PWM
-
MKE
6h 49m1 stop
$298United Airlines
Tue, Jan 13 - Tue, Jan 20
Delta Logo
6:40 am - 12:03 pm
MKE
-
PWM
4h 23m1 stop
Delta Logo
12:43 pm - 5:05 pm
PWM
-
MKE
5h 22m1 stop
$317Delta
Wed, Jan 28 - Wed, Feb 4
Delta Logo
5:45 pm - 11:22 pm
MKE
-
PWM
4h 37m1 stop
Delta Logo
2:35 pm - 8:58 pm
PWM
-
MKE
7h 23m1 stop
$328Delta
Fri, Jan 16 - Tue, Jan 20
United Airlines Logo
7:00 am - 2:39 pm
MKE
-
PWM
6h 39m1 stop
United Airlines Logo
6:00 am - 10:15 am
PWM
-
MKE
5h 15m1 stop
$338United Airlines
Fri, Jan 9 - Sat, Jan 17
United Airlines Logo
5:39 pm - 11:30 pm
MKE
-
PWM
4h 51m1 stop
United Airlines Logo
3:05 pm - 10:56 pm
PWM
-
MKE
8h 51m2 stops
$343United Airlines
Fri, Jan 9 - Sat, Jan 17
United Airlines Logo
6:00 am - 2:31 pm
MKE
-
PWM
7h 31m2 stops
United Airlines Logo
3:05 pm - 10:56 pm
PWM
-
MKE
8h 51m2 stops
$348United Airlines
Fri, Jan 9 - Sat, Jan 17
United Airlines Logo
7:00 am - 2:39 pm
MKE
-
PWM
6h 39m1 stop
United Airlines Logo
4:10 pm - 9:59 pm
PWM
-
MKE
6h 49m1 stop
$362United Airlines
Tue, Jan 6 - Fri, Jan 9
American Airlines Logo
9:30 am - 10:07 pm
MKE
-
PWM
11h 37m2 stops
American Airlines Logo
5:20 am - 12:21 pm
PWM
-
MKE
8h 01m1 stop
$364American Airlines
Wed, Jan 28 - Wed, Feb 4
United Airlines Logo
11:30 am - 11:27 pm
MKE
-
PWM
10h 57m2 stops
United Airlines Logo
4:10 pm - 8:48 pm
PWM
-
MKE
5h 38m1 stop
$367United Airlines
Tue, Jan 6 - Fri, Jan 9

Delta flights from Milwaukee to Portland, Maine

Our best Delta deals on Milwaukee to Portland, Maine flight tickets
Delta
Jan 28
MKE6:40 amMilwaukee-Mitchell
4h 23m
1 stop
PWM12:03 pmPortland
Feb 4
PWM12:43 pmPortland
5h 22m
1 stop
MKE5:05 pmMilwaukee-Mitchell
$317
Find similar
Delta
Jan 16
MKE5:45 pmMilwaukee-Mitchell
4h 37m
1 stop
PWM11:22 pmPortland
Jan 20
PWM2:35 pmPortland
7h 23m
1 stop
MKE8:58 pmMilwaukee-Mitchell
$328
Find similar
Delta
Jun 12
MKE4:20 pmMilwaukee-Mitchell
6h 33m
1 stop
PWM11:53 pmPortland
Jun 17
PWM6:00 amPortland
8h 44m
1 stop
MKE1:44 pmMilwaukee-Mitchell
$423
Find similar

American Airlines flights from Milwaukee to Portland, Maine

Our best American Airlines deals on Milwaukee to Portland, Maine flight tickets
American Airlines
Jan 28
MKE9:30 amMilwaukee-Mitchell
11h 37m
2 stops
PWM10:07 pmPortland
Feb 4
PWM5:20 amPortland
8h 01m
1 stop
MKE12:21 pmMilwaukee-Mitchell
$364
Find similar
American Airlines
Jan 16
MKE9:30 amMilwaukee-Mitchell
11h 37m
2 stops
PWM10:07 pmPortland
Jan 20
PWM12:46 pmPortland
10h 19m
2 stops
MKE10:05 pmMilwaukee-Mitchell
$474
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Milwaukee 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 December 15, 2025.
Use the filters below to find and compare flights from Milwaukee to Portland, Maine that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Tue 1/13

5:39 pm-11:27 pm

1 stop4h 48m

Portland

Tue 1/20

4:10 pm-9:59 pm

1 stop6h 49m

$293

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Tue 1/13

5:00 am-2:31 pm

2 stops8h 31m

Portland

Tue 1/20

4:10 pm-9:59 pm

1 stop6h 49m

$298

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Wed 1/28

6:40 am-12:03 pm

1 stop4h 23m

Portland

Wed 2/4

12:43 pm-5:05 pm

1 stop5h 22m

$317

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Fri 1/16

5:45 pm-11:22 pm

1 stop4h 37m

Portland

Tue 1/20

2:35 pm-8:58 pm

1 stop7h 23m

$328

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Fri 1/9

7:00 am-2:39 pm

1 stop6h 39m

Portland

Sat 1/17

6:00 am-10:15 am

1 stop5h 15m

$338

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Fri 1/9

5:39 pm-11:30 pm

1 stop4h 51m

Portland

Sat 1/17

3:05 pm-10:56 pm

2 stops8h 51m

$343

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Fri 1/9

6:00 am-2:31 pm

2 stops7h 31m

Portland

Sat 1/17

3:05 pm-10:56 pm

2 stops8h 51m

$348

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Tue 1/6

7:00 am-2:39 pm

1 stop6h 39m

Portland

Fri 1/9

4:10 pm-9:59 pm

1 stop6h 49m

$362

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Wed 1/28

9:30 am-10:07 pm

2 stops11h 37m

Portland

Wed 2/4

5:20 am-12:21 pm

1 stop8h 01m

$364

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Tue 1/6

11:30 am-11:27 pm

2 stops10h 57m

Portland

Fri 1/9

4:10 pm-8:48 pm

1 stop5h 38m

$367

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 Boston from

How to get the cheapest flight ticket from Milwaukee 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 typical price of a round-trip flight between Milwaukee and Portland, Maine?

What is the cheapest month to fly to Portland, Maine?

The cheapest month to fly to Portland, Maine from Milwaukee is in April. Flight prices, which tend to average around $297, are often lower during this time because this is during the off-season. If you aren’t able to travel to Portland, Maine during the month of April, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $340.

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 Milwaukee is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $361. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Monday is the most expensive day to depart from Milwaukee because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $472.

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 Milwaukee to Portland, Maine when you can find flight prices for as low as $376. 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 $426. Of course, these prices can vary depending on the time of year and what airport you fly to.

How far in advance should I book a flight to Portland, Maine?

You are more likely to see cheaper flights to Portland, Maine from Milwaukee when booking weeks ahead of your departure date. In general, you can expect to find flights to Portland, Maine for around $378 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Portland, Maine from Milwaukee for as low as $228 on momondo.

When to book flights from Milwaukee to Portland, Maine

Are you open to changing your travel dates? Check out the ideal times to fly from Milwaukee to Portland, Maine according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Milwaukee to Portland, Maine (MKE to PWM) flight deals and tips

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

Fastest flight time

4h 37m

Direct flights

None
The fastest flight from Milwaukee to Portland, Maine takes 4h 37m
There are no direct flights from Milwaukee to Portland, Maine. There are no popular flight routes from Milwaukee to Portland, Maine.
Search flight deals

  • How far is Milwaukee-Mitchell to Portland by plane?

    Portland is 885.6 mi away from Milwaukee-Mitchell. In terms of flight time, this usually takes a little over 4h 37m.

  • When did momondo last update prices for flights from Milwaukee-Mitchell Airport to Portland Airport?

    Prices for flights from Milwaukee-Mitchell Airport to Portland Airport are updated daily.

  • How many operators does momondo search for flights from Milwaukee-Mitchell Airport to Portland Airport?

  • How old do you have to be to fly from Milwaukee-Mitchell Airport to Portland Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Milwaukee-Mitchell Airport 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.

  • What is the most popular airline from Milwaukee to Portland, Maine?

Best airlines flying from Milwaukee to Portland, Maine

Compare and see reviews for airlines that fly from Milwaukee to Portland, Maine with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $238Free CancellationRating
7.2
11,052 reviews
Search American Airlines flights
SouthwestPriceFrom $246Free CancellationRating
7.9
4,250 reviews
Search Southwest flights
DeltaPriceFrom $251Free CancellationRating
7.9
8,007 reviews
Search Delta flights
United AirlinesPriceFrom $309Free CancellationRating
7.4
9,092 reviews
Search United Airlines flights

Traveling to a place near Boston?

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

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Milwaukee to Portland for you.

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

Yes. momondo allows you to filter the results for Milwaukee to Portland flights to just show those with flexible booking policies.

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

momondo helps you find the best flight between Milwaukee and Portland by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Of course. momondo tracks the price of Milwaukee to Portland flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Portland, Maine trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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