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Cheap flights from Portland to Milwaukee from $165

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 7/22. 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 Portland to Milwaukee

Cheap round-trip flights

Enter your travel dates to find the best prices.
Alaska Airlines Logo
5:00 am - 3:44 pm
PDX
-
MKE
8h 44m
1 stop
Alaska Airlines Logo
4:40 pm - 9:28 pm
MKE
-
PDX
6h 48m
1 stop
$329Alaska Airlines
Tue, Jun 2 - Wed, Jun 3
Delta Logo
9:39 pm - 9:08 am
PDX
-
MKE
9h 29m
1 stop
Delta Logo
5:00 pm - 10:02 pm
MKE
-
PDX
7h 02m
1 stop
$331Delta
Wed, Jun 3 - Sat, Jun 6
Alaska Airlines Logo
5:00 am - 3:44 pm
PDX
-
MKE
8h 44m
1 stop
Alaska Airlines Logo
4:40 pm - 9:28 pm
MKE
-
PDX
6h 48m
1 stop
$339Alaska Airlines
Tue, Jun 2 - Wed, Jun 3
American Airlines Logo
1:34 pm - 11:34 pm
PDX
-
MKE
8h 00m
1 stop
American Airlines Logo
10:00 am - 2:38 pm
MKE
-
PDX
6h 38m
1 stop
$342American Airlines
Wed, Jun 3 - Sat, Jun 6
Southwest Logo
10:40 am - 10:15 pm
PDX
-
MKE
9h 35m
2 stops
Southwest Logo
6:55 pm - 11:50 pm
MKE
-
PDX
6h 55m
1 stop
$347Southwest
Tue, Jun 9 - Tue, Jun 16
Delta Logo
12:33 am - 9:15 am
PDX
-
MKE
6h 42m
1 stop
Delta Logo
6:59 pm - 11:18 pm
MKE
-
PDX
6h 19m
1 stop
$355Delta
Sun, Jun 7 - Mon, Jun 15
American Airlines Logo
12:45 am - 11:18 am
PDX
-
MKE
8h 33m
1 stop
American Airlines Logo
6:01 am - 10:36 am
MKE
-
PDX
6h 35m
1 stop
$373American Airlines
Thu, Jul 2 - Tue, Jul 7
Alaska Airlines Logo
5:00 am - 3:44 pm
PDX
-
MKE
8h 44m
1 stop
Alaska Airlines Logo
4:40 pm - 9:28 pm
MKE
-
PDX
6h 48m
1 stop
$374Alaska Airlines
Tue, Jun 2 - Sat, Jun 6
American Airlines Logo
10:59 pm - 7:42 am
PDX
-
MKE
6h 43m
1 stop
American Airlines Logo
5:00 am - 10:25 am
MKE
-
PDX
7h 25m
1 stop
$382American Airlines
Mon, Jun 15 - Thu, Jun 25
Delta Logo
2:10 pm - 11:59 pm
PDX
-
MKE
7h 49m
1 stop
Delta Logo
6:59 pm - 11:18 pm
MKE
-
PDX
6h 19m
1 stop
$387Delta
Wed, Jun 10 - Mon, Jul 27

American Airlines flights from Portland to Milwaukee

Our best American Airlines deals on Portland to Milwaukee flight tickets
American Airlines
Jun 3
PDX1:34 pmPortland
8h 00m
1 stop
MKE11:34 pmMilwaukee-Mitchell
Jun 6
MKE10:00 amMilwaukee-Mitchell
6h 38m
1 stop
PDX2:38 pmPortland
$342
American Airlines
Jul 2
PDX12:45 amPortland
8h 33m
1 stop
MKE11:18 amMilwaukee-Mitchell
Jul 7
MKE6:01 amMilwaukee-Mitchell
6h 35m
1 stop
PDX10:36 amPortland
$373
American Airlines
Jun 15
PDX10:59 pmPortland
6h 43m
1 stop
MKE7:42 amMilwaukee-Mitchell
Jun 25
MKE5:00 amMilwaukee-Mitchell
7h 25m
1 stop
PDX10:25 amPortland
$382

Southwest flights from Portland to Milwaukee

Our best Southwest deals on Portland to Milwaukee flight tickets
Southwest
Jun 9
PDX10:40 amPortland
9h 35m
2 stops
MKE10:15 pmMilwaukee-Mitchell
Jun 16
MKE6:55 pmMilwaukee-Mitchell
6h 55m
1 stop
PDX11:50 pmPortland
$347
Southwest
Jun 17
PDX3:40 pmPortland
7h 15m
1 stop
MKE12:55 amMilwaukee-Mitchell
Jun 23
MKE6:55 pmMilwaukee-Mitchell
6h 55m
1 stop
PDX11:50 pmPortland
$394
Southwest
Jul 1
PDX3:40 pmPortland
7h 15m
1 stop
MKE12:55 amMilwaukee-Mitchell
Jul 7
MKE3:40 pmMilwaukee-Mitchell
8h 55m
2 stops
PDX10:35 pmPortland
$399

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 May 12, 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

Tue 6/2

5:00 am-3:44 pm

1 stop8h 44m

Milwaukee-Mitchell

Wed 6/3

4:40 pm-9:28 pm

1 stop6h 48m

$329

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Wed 6/3

9:39 pm-9:08 am

1 stop9h 29m

Milwaukee-Mitchell

Sat 6/6

5:00 pm-10:02 pm

1 stop7h 02m

$331

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 6/2

5:00 am-3:44 pm

1 stop8h 44m

Milwaukee-Mitchell

Wed 6/3

4:40 pm-9:28 pm

1 stop6h 48m

$339

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Wed 6/3

1:34 pm-11:34 pm

1 stop8h 00m

Milwaukee-Mitchell

Sat 6/6

10:00 am-2:38 pm

1 stop6h 38m

$342

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 6/9

10:40 am-10:15 pm

2 stops9h 35m

Milwaukee-Mitchell

Tue 6/16

6:55 pm-11:50 pm

1 stop6h 55m

$347
Quickest round-trip

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Sun 6/7

12:33 am-9:15 am

1 stop6h 42m

Milwaukee-Mitchell

Mon 6/15

6:59 pm-11:18 pm

1 stop6h 19m

$355

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Thu 7/2

12:45 am-11:18 am

1 stop8h 33m

Milwaukee-Mitchell

Tue 7/7

6:01 am-10:36 am

1 stop6h 35m

$373

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 6/2

5:00 am-3:44 pm

1 stop8h 44m

Milwaukee-Mitchell

Sat 6/6

4:40 pm-9:28 pm

1 stop6h 48m

$374

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Mon 6/15

10:59 pm-7:42 am

1 stop6h 43m

Milwaukee-Mitchell

Thu 6/25

5:00 am-10:25 am

1 stop7h 25m

$382

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Wed 6/10

2:10 pm-11:59 pm

1 stop7h 49m

Milwaukee-Mitchell

Mon 7/27

6:59 pm-11:18 pm

1 stop6h 19m

$387

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 November is another great option to travel to Milwaukee, with average flight prices from Portland averaging around $381.

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 $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 $219 on momondo.

Can stopping save me money on Portland to Milwaukee flights?

You could potentially save up to 18% 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 May 2026, prices for Portland to Milwaukee flights are approximately 33% 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

6h 20m

Direct flights

None
The fastest flight from Portland to Milwaukee takes 6h 20m
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 6h 20m.

  • 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
8,446 reviews
Search Delta flights
American AirlinesPriceFrom $209Free CancellationRating
7.1
11,661 reviews
Search American Airlines flights
United AirlinesPriceFrom $278Free CancellationRating
7.4
9,701 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $307Free CancellationRating
7.9
12,354 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $322Free CancellationRating
8.0
4,295 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
West Bend
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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