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Cheap flights from Portland to Milwaukee from $125

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 to Milwaukee departing on 3/29. 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

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Find the cheapest flights from Portland to Milwaukee

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
11:48 am - 5:34 pm
PDX
-
MKE
27h 46m
1 stop
Frontier Logo
5:05 pm - 11:52 am
MKE
-
PDX
20h 47m
1 stop
$216Frontier
Thu, Apr 23 - Mon, Apr 27
Frontier Logo
11:48 am - 5:44 pm
PDX
-
MKE
27h 56m
1 stop
Frontier Logo
5:05 pm - 11:52 am
MKE
-
PDX
20h 47m
1 stop
$261Frontier
Thu, Apr 16 - Mon, Apr 20
American Airlines Logo
11:23 pm - 11:30 am
PDX
-
MKE
10h 07m
1 stop
American Airlines Logo
6:45 pm - 11:52 pm
MKE
-
PDX
7h 07m
1 stop
$269American Airlines
Tue, May 19 - Tue, May 26
American Airlines Logo
11:56 am - 10:27 pm
PDX
-
MKE
8h 31m
1 stop
American Airlines Logo
5:00 pm - 11:54 pm
MKE
-
PDX
8h 54m
1 stop
$297American Airlines
Tue, Apr 14 - Thu, Apr 16
Southwest Logo
2:50 pm - 10:30 pm
PDX
-
MKE
5h 40m
1 stop
Southwest Logo
2:40 pm - 11:00 pm
MKE
-
PDX
10h 20m
1 stop
$320Southwest
Thu, May 28 - Wed, Jun 3
American Airlines Logo
6:00 am - 5:01 pm
PDX
-
MKE
9h 01m
1 stop
American Airlines Logo
4:26 pm - 11:57 pm
MKE
-
PDX
9h 31m
1 stop
$324American Airlines
Fri, Apr 24 - Tue, Apr 28
United Airlines Logo
12:50 pm - 9:21 pm
PDX
-
MKE
6h 31m
1 stop
United Airlines Logo
6:50 am - 11:46 am
MKE
-
PDX
6h 56m
1 stop
$325United Airlines
Sat, Apr 25 - Tue, Apr 28
Southwest Logo
1:35 pm - 11:15 pm
PDX
-
MKE
7h 40m
1 stop
Southwest Logo
4:05 pm - 11:00 pm
MKE
-
PDX
8h 55m
2 stops
$330Southwest
Sat, Apr 18 - Tue, Apr 21
Southwest Logo
6:00 am - 10:20 pm
PDX
-
MKE
14h 20m
2 stops
Southwest Logo
5:45 pm - 11:00 pm
MKE
-
PDX
7h 15m
1 stop
$331Southwest
Thu, May 28 - Wed, Jun 3
Alaska Airlines Logo
8:45 am - 11:58 pm
PDX
-
MKE
13h 13m
1 stop
Alaska Airlines Logo
4:40 pm - 9:28 pm
MKE
-
PDX
6h 48m
1 stop
$333Alaska Airlines
Mon, May 11 - Sat, May 30

United Airlines flights from Portland to Milwaukee

Our best United Airlines deals on Portland to Milwaukee flight tickets
United Airlines
Apr 25
PDX12:50 pmPortland
6h 31m
1 stop
MKE9:21 pmMilwaukee-Mitchell
Apr 28
MKE6:50 amMilwaukee-Mitchell
6h 56m
1 stop
PDX11:46 amPortland
$325
United Airlines
May 5
PDX11:55 pmPortland
5h 54m
1 stop
MKE7:49 amMilwaukee-Mitchell
May 6
MKE12:00 pmMilwaukee-Mitchell
9h 38m
1 stop
PDX7:38 pmPortland
$369
United Airlines
May 5
PDX5:30 amPortland
13h 57m
3 stops
MKE9:27 pmMilwaukee-Mitchell
May 6
MKE3:25 pmMilwaukee-Mitchell
9h 10m
1 stop
PDX10:35 pmPortland
$380

Southwest flights from Portland to Milwaukee

Our best Southwest deals on Portland to Milwaukee flight tickets
Southwest
May 28
PDX2:50 pmPortland
5h 40m
1 stop
MKE10:30 pmMilwaukee-Mitchell
Jun 3
MKE2:40 pmMilwaukee-Mitchell
10h 20m
1 stop
PDX11:00 pmPortland
$320
Southwest
Apr 18
PDX1:35 pmPortland
7h 40m
1 stop
MKE11:15 pmMilwaukee-Mitchell
Apr 21
MKE4:05 pmMilwaukee-Mitchell
8h 55m
2 stops
PDX11:00 pmPortland
$330
Southwest
May 28
PDX6:00 amPortland
14h 20m
2 stops
MKE10:20 pmMilwaukee-Mitchell
Jun 3
MKE5:45 pmMilwaukee-Mitchell
7h 15m
1 stop
PDX11:00 pmPortland
$331

momondo Fare Finder

 
Customize your flight search to find flights from Portland 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 March 24, 2026.
Use the filters below to find and compare flights from Portland to Milwaukee that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Thu 4/23

11:48 am-5:34 pm

1 stop27h 46m

Milwaukee-Mitchell

Mon 4/27

5:05 pm-11:52 am

1 stop20h 47m

$216

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Thu 4/16

11:48 am-5:44 pm

1 stop27h 56m

Milwaukee-Mitchell

Mon 4/20

5:05 pm-11:52 am

1 stop20h 47m

$261

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 5/19

11:23 pm-11:30 am

1 stop10h 07m

Milwaukee-Mitchell

Tue 5/26

6:45 pm-11:52 pm

1 stop7h 07m

$269

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 4/14

11:56 am-10:27 pm

1 stop8h 31m

Milwaukee-Mitchell

Thu 4/16

5:00 pm-11:54 pm

1 stop8h 54m

$297

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Thu 5/28

2:50 pm-10:30 pm

1 stop5h 40m

Milwaukee-Mitchell

Wed 6/3

2:40 pm-11:00 pm

1 stop10h 20m

$320

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Fri 4/24

6:00 am-5:01 pm

1 stop9h 01m

Milwaukee-Mitchell

Tue 4/28

4:26 pm-11:57 pm

1 stop9h 31m

$324
Quickest round-trip

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Sat 4/25

12:50 pm-9:21 pm

1 stop6h 31m

Milwaukee-Mitchell

Tue 4/28

6:50 am-11:46 am

1 stop6h 56m

$325

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Sat 4/18

1:35 pm-11:15 pm

1 stop7h 40m

Milwaukee-Mitchell

Tue 4/21

4:05 pm-11:00 pm

2 stops8h 55m

$330

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Thu 5/28

6:00 am-10:20 pm

2 stops14h 20m

Milwaukee-Mitchell

Wed 6/3

5:45 pm-11:00 pm

1 stop7h 15m

$331

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Mon 5/11

8:45 am-11:58 pm

1 stop13h 13m

Milwaukee-Mitchell

Sat 5/30

4:40 pm-9:28 pm

1 stop6h 48m

$333

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 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 is in January. Flight prices, which tend to average around $324, are often lower during this time because this is during the off-season. The month of August is another great option to travel to Milwaukee, with average flight prices from Portland averaging around $358.

How far in advance should I book a flight to Milwaukee?

You are more likely to see cheaper flights to Milwaukee from Portland when booking weeks ahead of your departure date. In general, you can expect to find flights to Milwaukee for around $444 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Milwaukee from Portland for as low as $253 on momondo.

Can stopping save me money on Portland to Milwaukee flights?

You could potentially save up to 6% on your flight if you consider stops on a Portland to Milwaukee flight.

How have Portland to Milwaukee flight prices changed over time?

As of March 2026, prices for Portland to Milwaukee flights are approximately 18% more expensive when compared to flights at the same time last year.

When to book flights from Portland to Milwaukee

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

Cheap Portland to Milwaukee (PDX to MKE) flight deals and tips

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

Fastest flight time

5h 40m

Direct flights

None
The fastest flight from Portland to Milwaukee takes 5h 40m
There are no direct flights from Portland to Milwaukee. There are no popular flight routes from Portland to Milwaukee.
Search flight deals

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

    A flight from Portland to Milwaukee-Mitchell will travel around 1713.7 mi. A reasonable flight in good conditions will take 5h 40m.

  • 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 were last updated today.

  • 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?

    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 Portland Airport to Milwaukee-Mitchell Airport.

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

    The required travel and health documents for your Milwaukee-Mitchell Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Milwaukee-Mitchell Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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

Best airlines flying from Portland to Milwaukee

Compare and see reviews for airlines that fly from Portland to Milwaukee with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $88Free CancellationRating
7.9
8,320 reviews
Search Delta flights
American AirlinesPriceFrom $209Free CancellationRating
7.1
11,492 reviews
Search American Airlines flights
United AirlinesPriceFrom $278Free CancellationRating
7.4
9,469 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $307Free CancellationRating
7.9
12,102 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $328Free CancellationRating
8.0
4,329 reviews
Search Southwest 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
Pewaukee
Kohler
Port Washington
West Bend
New Berlin
Grafton

Why use momondo?

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

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 Portland to Milwaukee for 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 you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Milwaukee from Portland.

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

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

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