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Cheap flights from Portland to Milwaukee from $154

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 9/23. 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 to Milwaukee

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
11:34 pm - 7:49 am
PDX
-
MKE
6h 15m
1 stop
American Airlines Logo
6:48 pm - 11:59 pm
MKE
-
PDX
7h 11m
1 stop
$307American Airlines
Thu, Aug 20 - Mon, Aug 24
Southwest Logo
12:20 pm - 9:25 pm
PDX
-
MKE
7h 05m
1 stop
Southwest Logo
4:35 pm - 11:05 pm
MKE
-
PDX
8h 30m
1 stop
$308Southwest
Thu, Aug 20 - Mon, Aug 24
American Airlines Logo
5:18 am - 5:00 pm
PDX
-
MKE
9h 42m
1 stop
American Airlines Logo
5:00 am - 11:34 am
MKE
-
PDX
8h 34m
1 stop
$309American Airlines
Sat, Aug 15 - Sat, Aug 22
American Airlines Logo
11:15 pm - 8:02 am
PDX
-
MKE
6h 47m
1 stop
American Airlines Logo
6:40 pm - 12:55 am
MKE
-
PDX
8h 15m
1 stop
$312American Airlines
Tue, Jul 28 - Tue, Aug 4
Southwest Logo
5:00 am - 1:30 pm
PDX
-
MKE
6h 30m
1 stop
Southwest Logo
6:20 am - 2:45 pm
MKE
-
PDX
10h 25m
2 stops
$314Southwest
Thu, Oct 1 - Tue, Oct 6
Delta Logo
12:25 am - 9:18 am
PDX
-
MKE
6h 53m
1 stop
Delta Logo
11:00 am - 5:31 pm
MKE
-
PDX
8h 31m
1 stop
$317Delta
Tue, Sep 22 - Sat, Sep 26
American Airlines Logo
11:34 pm - 7:49 am
PDX
-
MKE
6h 15m
1 stop
American Airlines Logo
5:00 am - 11:34 am
MKE
-
PDX
8h 34m
1 stop
$318American Airlines
Sat, Aug 15 - Sat, Aug 22
American Airlines Logo
11:34 pm - 7:49 am
PDX
-
MKE
6h 15m
1 stop
American Airlines Logo
6:48 pm - 11:59 pm
MKE
-
PDX
7h 11m
1 stop
$320American Airlines
Wed, Aug 12 - Thu, Aug 20
American Airlines Logo
12:01 pm - 9:48 pm
PDX
-
MKE
7h 47m
1 stop
American Airlines Logo
5:43 pm - 11:23 pm
MKE
-
PDX
7h 40m
1 stop
$321American Airlines
Wed, Sep 23 - Wed, Sep 30
United Airlines Logo
4:07 pm - 11:59 pm
PDX
-
MKE
5h 52m
1 stop
United Airlines Logo
2:20 pm - 9:10 pm
MKE
-
PDX
8h 50m
2 stops
$322United Airlines
Wed, Sep 23 - Sat, Sep 26

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United Airlines flights from Portland to Milwaukee

Our best United Airlines deals on Portland to Milwaukee flight tickets
United Airlines
Sep 23
PDX4:07 pmPortland
5h 52m
1 stop
MKE11:59 pmMilwaukee-Mitchell
Sep 26
MKE2:20 pmMilwaukee-Mitchell
8h 50m
2 stops
PDX9:10 pmPortland
$322
United Airlines
Sep 23
PDX10:56 amPortland
10h 41m
1 stop
MKE11:37 pmMilwaukee-Mitchell
Sep 26
MKE2:20 pmMilwaukee-Mitchell
10h 37m
2 stops
PDX10:57 pmPortland
$412
United Airlines
Sep 9
PDX11:02 pmPortland
8h 58m
1 stop
MKE10:00 amMilwaukee-Mitchell
Sep 15
MKE12:05 pmMilwaukee-Mitchell
12h 40m
2 stops
PDX10:45 pmPortland
$422

Southwest flights from Portland to Milwaukee

Our best Southwest deals on Portland to Milwaukee flight tickets
Southwest
Aug 20
PDX12:20 pmPortland
7h 05m
1 stop
MKE9:25 pmMilwaukee-Mitchell
Aug 24
MKE4:35 pmMilwaukee-Mitchell
8h 30m
1 stop
PDX11:05 pmPortland
$308
Southwest
Aug 26
PDX5:50 amPortland
12h 15m
1 stop
MKE8:05 pmMilwaukee-Mitchell
Aug 29
MKE11:40 amMilwaukee-Mitchell
11h 25m
2 stops
PDX9:05 pmPortland
$328
Southwest
Aug 20
PDX9:20 amPortland
10h 05m
2 stops
MKE9:25 pmMilwaukee-Mitchell
Aug 24
MKE6:45 amMilwaukee-Mitchell
6h 10m
1 stop
PDX10:55 amPortland
$342

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 June 29, 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
Quickest round-trip

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Thu 8/20

11:34 pm-7:49 am

1 stop6h 15m

Milwaukee-Mitchell

Mon 8/24

6:48 pm-11:59 pm

1 stop7h 11m

$307

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Thu 8/20

12:20 pm-9:25 pm

1 stop7h 05m

Milwaukee-Mitchell

Mon 8/24

4:35 pm-11:05 pm

1 stop8h 30m

$308

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Sat 8/15

5:18 am-5:00 pm

1 stop9h 42m

Milwaukee-Mitchell

Sat 8/22

5:00 am-11:34 am

1 stop8h 34m

$309

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 7/28

11:15 pm-8:02 am

1 stop6h 47m

Milwaukee-Mitchell

Tue 8/4

6:40 pm-12:55 am

1 stop8h 15m

$312

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Thu 10/1

5:00 am-1:30 pm

1 stop6h 30m

Milwaukee-Mitchell

Tue 10/6

6:20 am-2:45 pm

2 stops10h 25m

$314

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 9/22

12:25 am-9:18 am

1 stop6h 53m

Milwaukee-Mitchell

Sat 9/26

11:00 am-5:31 pm

1 stop8h 31m

$317

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Sat 8/15

11:34 pm-7:49 am

1 stop6h 15m

Milwaukee-Mitchell

Sat 8/22

5:00 am-11:34 am

1 stop8h 34m

$318

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Wed 8/12

11:34 pm-7:49 am

1 stop6h 15m

Milwaukee-Mitchell

Thu 8/20

6:48 pm-11:59 pm

1 stop7h 11m

$320

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Wed 9/23

12:01 pm-9:48 pm

1 stop7h 47m

Milwaukee-Mitchell

Wed 9/30

5:43 pm-11:23 pm

1 stop7h 40m

$321

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Wed 9/23

4:07 pm-11:59 pm

1 stop5h 52m

Milwaukee-Mitchell

Sat 9/26

2:20 pm-9:10 pm

2 stops8h 50m

$322

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 typical price of a round-trip flight between Portland and Milwaukee?

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 $390.

How far in advance should I book a flight from Portland 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 $460 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 $126 on momondo.

Can stopping save me money on Portland to Milwaukee flights?

You could potentially save up to 2% 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 June 2026, prices for Portland to Milwaukee flights are approximately 40% 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 44m

Direct flights

None
The fastest flight from Portland to Milwaukee takes 5h 44m
There are no direct flights from Portland to Milwaukee. There are no popular flight routes from Portland to Milwaukee.
Search flight deals

Frequently asked questions about flying from Portland to Milwaukee

  • 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 44m.

  • 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
7.8
8,449 reviews
Search Delta flights
American AirlinesPriceFrom $209Free CancellationRating
7.1
11,768 reviews
Search American Airlines flights
United AirlinesPriceFrom $278Free CancellationRating
7.4
9,894 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $304Free CancellationRating
7.9
12,593 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $322Free CancellationRating
7.9
4,246 reviews
Search Southwest flights

  • Southwest Flights From Portland to Milwaukee

    Southwest is one of the most popular airlines flying from Portland to Milwaukee, operating 1 flight/week on average for this route. A good Southwest flight deal for Portland to Milwaukee starts from $322 round-trip, up to an average price of $536. Our users have rated Southwest at 7.9/10.

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
Pewaukee
Port Washington
Kohler
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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