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Cheap flights from Portland, Maine to Milwaukee from $163

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Portland, Maine to Milwaukee 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.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Portland, Maine to Milwaukee

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
6:03 am - 12:38 pmPWM  Portland-MKE Milwaukee-Mitchell
7h 35m1 stop Chicago O'Hare Intl
United Airlines Logo
7:18 am - 2:34 pmMKE  Milwaukee-Mitchell-PWM Portland
6h 16m1 stop Chicago O'Hare Intl
$335United Airlines
Sat, Aug 22 - Tue, Aug 25
United Airlines Logo
6:03 am - 10:00 amPWM  Portland-MKE Milwaukee-Mitchell
4h 57m1 stop Chicago O'Hare Intl
United Airlines Logo
2:20 pm - 9:23 pmMKE  Milwaukee-Mitchell-PWM Portland
6h 03m1 stop Chicago O'Hare Intl
$338United Airlines
Sun, Sep 6 - Sat, Sep 12
Southwest Logo
5:40 am - 12:10 pmPWM  Portland-MKE Milwaukee-Mitchell
7h 30m1 stop Baltimore/Washington
Southwest Logo
10:30 am - 9:10 pmMKE  Milwaukee-Mitchell-PWM Portland
9h 40m2 stops Orlando Baltimore/Washington
$340Southwest
Sat, Aug 22 - Tue, Aug 25
United Airlines Logo
6:03 am - 10:00 amPWM  Portland-MKE Milwaukee-Mitchell
4h 57m1 stop Chicago O'Hare Intl
United Airlines Logo
5:00 am - 2:38 pmMKE  Milwaukee-Mitchell-PWM Portland
8h 38m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl
$340United Airlines
Sat, Aug 22 - Tue, Aug 25
Delta Logo
5:28 pm - 9:24 pmPWM  Portland-MKE Milwaukee-Mitchell
4h 56m1 stop New York LaGuardia
Delta Logo
5:55 pm - 11:21 pmMKE  Milwaukee-Mitchell-PWM Portland
4h 26m1 stop New York LaGuardia
$351Delta
Thu, Nov 5 - Mon, Nov 9
Delta Logo
4:03 pm - 8:40 pmPWM  Portland-MKE Milwaukee-Mitchell
5h 37m1 stop New York John F Kennedy Intl
Delta Logo
5:55 pm - 11:21 pmMKE  Milwaukee-Mitchell-PWM Portland
4h 26m1 stop New York LaGuardia
$351Delta
Sat, Dec 12 - Mon, Dec 14
American Airlines Logo
12:48 pm - 6:35 pmPWM  Portland-MKE Milwaukee-Mitchell
6h 47m1 stop Chicago O'Hare Intl
American Airlines Logo
6:01 am - 11:37 amMKE  Milwaukee-Mitchell-PWM Portland
4h 36m1 stop Washington, D.C. Reagan-National
$351American Airlines
Tue, Dec 1 - Tue, Dec 8
American Airlines Logo
6:00 am - 12:14 pmPWM  Portland-MKE Milwaukee-Mitchell
7h 14m1 stop Philadelphia
American Airlines Logo
5:00 am - 12:11 pmMKE  Milwaukee-Mitchell-PWM Portland
6h 11m1 stop Chicago O'Hare Intl
$351American Airlines
Sat, Oct 17 - Mon, Oct 19
Southwest Logo
5:20 am - 10:45 amPWM  Portland-MKE Milwaukee-Mitchell
6h 25m2 stops Baltimore/Washington Chicago Midway
Southwest Logo
5:00 pm - 9:50 pmMKE  Milwaukee-Mitchell-PWM Portland
3h 50m1 stop Chicago Midway
$356Southwest
Thu, Oct 22 - Mon, Oct 26
Southwest Logo
1:05 pm - 8:20 pmPWM  Portland-MKE Milwaukee-Mitchell
8h 15m2 stops Baltimore/Washington Lambert-St Louis
Southwest Logo
8:15 am - 3:30 pmMKE  Milwaukee-Mitchell-PWM Portland
6h 15m1 stop Nashville Intl
$360Southwest
Fri, Sep 4 - Sun, Sep 6

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American Airlines flights from Portland, Maine to Milwaukee

Our best American Airlines deals on Portland, Maine to Milwaukee flight tickets
American Airlines
Oct 17
PWM6:00 amPortland
7h 14m
1 stop
MKE12:14 pmMilwaukee-Mitchell
Oct 19
MKE5:00 amMilwaukee-Mitchell
6h 11m
1 stop
PWM12:11 pmPortland
$351
American Airlines
Sep 4
PWM6:46 pmPortland
5h 28m
1 stop
MKE11:14 pmMilwaukee-Mitchell
Sep 6
MKE11:27 amMilwaukee-Mitchell
6h 45m
1 stop
PWM7:12 pmPortland
$355
American Airlines
Sep 11
PWM12:24 pmPortland
5h 17m
1 stop
MKE4:41 pmMilwaukee-Mitchell
Sep 13
MKE2:48 pmMilwaukee-Mitchell
7h 59m
1 stop
PWM11:47 pmPortland
$371

United Airlines flights from Portland, Maine to Milwaukee

Our best United Airlines deals on Portland, Maine to Milwaukee flight tickets
United Airlines
Aug 22
PWM6:03 amPortland
7h 35m
1 stop
MKE12:38 pmMilwaukee-Mitchell
Aug 25
MKE7:18 amMilwaukee-Mitchell
6h 16m
1 stop
PWM2:34 pmPortland
$335
United Airlines
Sep 6
PWM6:03 amPortland
4h 57m
1 stop
MKE10:00 amMilwaukee-Mitchell
Sep 12
MKE2:20 pmMilwaukee-Mitchell
6h 03m
1 stop
PWM9:23 pmPortland
$338
United Airlines
Aug 22
PWM6:03 amPortland
4h 57m
1 stop
MKE10:00 amMilwaukee-Mitchell
Aug 25
MKE5:00 amMilwaukee-Mitchell
8h 38m
2 stops
PWM2:38 pmPortland
$340

momondo Fare Finder

 
Customize your flight search to find flights from Portland, Maine to Milwaukee 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 8, 2026.
Use the filters below to find and compare flights from Portland, Maine to Milwaukee that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandMilwaukee

PWM Portland - MKE Milwaukee-Mitchell

PWMMKE

Portland

Sat 8/22

6:03 am-12:38 pm

1 stop7h 35m

Milwaukee-Mitchell

Tue 8/25

7:18 am-2:34 pm

1 stop6h 16m

$335

PortlandMilwaukee

PWM Portland - MKE Milwaukee-Mitchell

PWMMKE

Portland

Sun 9/6

6:03 am-10:00 am

1 stop4h 57m

Milwaukee-Mitchell

Sat 9/12

2:20 pm-9:23 pm

1 stop6h 03m

$338

PortlandMilwaukee

PWM Portland - MKE Milwaukee-Mitchell

PWMMKE

Portland

Sat 8/22

5:40 am-12:10 pm

1 stop7h 30m

Milwaukee-Mitchell

Tue 8/25

10:30 am-9:10 pm

2 stops9h 40m

$340

PortlandMilwaukee

PWM Portland - MKE Milwaukee-Mitchell

PWMMKE

Portland

Sat 8/22

6:03 am-10:00 am

1 stop4h 57m

Milwaukee-Mitchell

Tue 8/25

5:00 am-2:38 pm

2 stops8h 38m

$340
Quickest round-trip

PortlandMilwaukee

PWM Portland - MKE Milwaukee-Mitchell

PWMMKE

Portland

Thu 11/5

5:28 pm-9:24 pm

1 stop4h 56m

Milwaukee-Mitchell

Mon 11/9

5:55 pm-11:21 pm

1 stop4h 26m

$351

PortlandMilwaukee

PWM Portland - MKE Milwaukee-Mitchell

PWMMKE

Portland

Sat 12/12

4:03 pm-8:40 pm

1 stop5h 37m

Milwaukee-Mitchell

Mon 12/14

5:55 pm-11:21 pm

1 stop4h 26m

$351

PortlandMilwaukee

PWM Portland - MKE Milwaukee-Mitchell

PWMMKE

Portland

Tue 12/1

12:48 pm-6:35 pm

1 stop6h 47m

Milwaukee-Mitchell

Tue 12/8

6:01 am-11:37 am

1 stop4h 36m

$351

PortlandMilwaukee

PWM Portland - MKE Milwaukee-Mitchell

PWMMKE

Portland

Sat 10/17

6:00 am-12:14 pm

1 stop7h 14m

Milwaukee-Mitchell

Mon 10/19

5:00 am-12:11 pm

1 stop6h 11m

$351

PortlandMilwaukee

PWM Portland - MKE Milwaukee-Mitchell

PWMMKE

Portland

Thu 10/22

5:20 am-10:45 am

2 stops6h 25m

Milwaukee-Mitchell

Mon 10/26

5:00 pm-9:50 pm

1 stop3h 50m

$356

PortlandMilwaukee

PWM Portland - MKE Milwaukee-Mitchell

PWMMKE

Portland

Fri 9/4

1:05 pm-8:20 pm

2 stops8h 15m

Milwaukee-Mitchell

Sun 9/6

8:15 am-3:30 pm

1 stop6h 15m

$360

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 Milwaukee from

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

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 month to fly to Milwaukee?

The cheapest month to fly to Milwaukee from Portland, Maine is in November. Flight prices, which tend to average around $335, are often lower during this time because this is during the off-season. The month of February is another great option to travel to Milwaukee, with average flight prices from Portland, Maine averaging around $348.

When to book flights from Portland, Maine to Milwaukee

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

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

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

Fastest flight time

4h 51m

Direct flights

None
The fastest flight from Portland, Maine to Milwaukee takes 4h 51m
There are no direct flights from Portland, Maine to Milwaukee. There are no popular flight routes from Portland, Maine to Milwaukee.
Search flight deals

Frequently asked questions about flying from Portland, Maine to Milwaukee

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

    The distance between Portland and Milwaukee-Mitchell is about 885.6 mi. By plane, this route typically takes 4h 51m.

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

    Prices for flights from Portland Airport to Milwaukee-Mitchell Airport are refreshed on a daily basis.

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

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

  • What documentation or ID do you need to fly to Milwaukee-Mitchell Airport?

    The travel and health documents required for your trip to Milwaukee-Mitchell Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Milwaukee-Mitchell Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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

Best airlines flying from Portland, Maine to Milwaukee

Compare and see reviews for airlines that fly from Portland, Maine to Milwaukee with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $272Free CancellationRating
7.8
8,504 reviews
Search Delta flights
United AirlinesPriceFrom $316Free CancellationRating
7.4
10,085 reviews
Search United Airlines flights
SouthwestPriceFrom $324Free CancellationRating
8.0
4,215 reviews
Search Southwest flights
American AirlinesPriceFrom $349Free CancellationRating
7.1
11,885 reviews
Search American Airlines flights

Traveling to a place near Milwaukee?

Book flights to Milwaukee if you plan to visit one of these locations
Sheboygan
Waukesha
Wauwatosa
Oak Creek
Mequon
Glendale
West Bend
Port Washington
Pewaukee
Kohler
New Berlin
Grafton

Why use momondo?

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

It is quick and easy to find Portland to Milwaukee flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Milwaukee that suits you.

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

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

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

Once all potential Portland to Milwaukee flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

If you are simply researching potential flights to Milwaukee, momondo offers a useful price alert feature which will track prices for flights to Milwaukee from Portland and alert you when they change.

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