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Cheap flights from Portland to Milwaukee from $156

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 9/30. 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.
Southwest Logo
6:00 am - 7:50 pmPDX  Portland-MKE Milwaukee-Mitchell
11h 50m1 stop Phoenix Sky Harbor Intl
Southwest Logo
6:20 pm - 11:20 pmMKE  Milwaukee-Mitchell-PDX Portland
7h 00m1 stop Phoenix Sky Harbor Intl
$269Southwest
Sat, Sep 5 - Fri, Sep 11
Southwest Logo
6:00 am - 7:50 pmPDX  Portland-MKE Milwaukee-Mitchell
11h 50m1 stop Phoenix Sky Harbor Intl
Southwest Logo
5:45 am - 7:15 pmMKE  Milwaukee-Mitchell-PDX Portland
15h 30m2 stops Chicago Midway Phoenix Sky Harbor Intl
$280Southwest
Sat, Sep 5 - Fri, Sep 11
Delta Logo
11:35 am - 9:09 pmPDX  Portland-MKE Milwaukee-Mitchell
7h 34m1 stop Minneapolis St Paul
Delta Logo
6:30 am - 12:37 pmMKE  Milwaukee-Mitchell-PDX Portland
8h 07m1 stop Minneapolis St Paul
$311Delta
Wed, Sep 23 - Tue, Sep 29
Delta Logo
11:12 pm - 8:39 amPDX  Portland-MKE Milwaukee-Mitchell
7h 27m1 stop Detroit Metropolitan Wayne County
Delta Logo
2:59 pm - 9:40 pmMKE  Milwaukee-Mitchell-PDX Portland
8h 41m1 stop Atlanta Hartsfield-Jackson
$311Delta
Thu, Oct 15 - Wed, Oct 21
American Airlines Logo
11:08 pm - 8:01 amPDX  Portland-MKE Milwaukee-Mitchell
6h 53m1 stop Chicago O'Hare Intl
American Airlines Logo
5:43 pm - 11:23 pmMKE  Milwaukee-Mitchell-PDX Portland
7h 40m1 stop Dallas/Fort Worth
$311American Airlines
Thu, Sep 10 - Mon, Sep 14
American Airlines Logo
11:58 am - 9:52 pmPDX  Portland-MKE Milwaukee-Mitchell
7h 54m1 stop Dallas/Fort Worth
American Airlines Logo
7:40 am - 12:33 pmMKE  Milwaukee-Mitchell-PDX Portland
6h 53m1 stop Chicago O'Hare Intl
$311American Airlines
Wed, Oct 28 - Thu, Nov 5
United Airlines Logo
8:15 am - 5:30 pmPDX  Portland-MKE Milwaukee-Mitchell
7h 15m1 stop Chicago O'Hare Intl
United Airlines Logo
5:00 am - 9:29 amMKE  Milwaukee-Mitchell-PDX Portland
6h 29m1 stop Chicago O'Hare Intl
$314United Airlines
Fri, Sep 11 - Wed, Sep 16
United Airlines Logo
8:40 am - 5:08 pmPDX  Portland-MKE Milwaukee-Mitchell
6h 28m1 stop Denver Intl
United Airlines Logo
3:52 pm - 10:52 pmMKE  Milwaukee-Mitchell-PDX Portland
9h 00m1 stop Chicago O'Hare Intl
$355United Airlines
Sat, Sep 12 - Fri, Sep 18
Alaska Airlines Logo
7:09 am - 4:19 pmPDX  Portland-MKE Milwaukee-Mitchell
7h 10m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
4:31 pm - 9:43 amMKE  Milwaukee-Mitchell-PDX Portland
19h 12m2 stops Seattle/Tacoma Intl San Diego
$393Alaska Airlines
Tue, Oct 27 - Tue, Nov 3
Alaska Airlines Logo
5:00 am - 1:52 pmPDX  Portland-MKE Milwaukee-Mitchell
6h 52m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
2:55 pm - 12:10 amMKE  Milwaukee-Mitchell-PDX Portland
11h 15m2 stops Chicago O'Hare Intl Seattle/Tacoma Intl
$416Alaska Airlines
Tue, Dec 8 - Thu, Dec 10

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Southwest flights from Portland to Milwaukee

Our best Southwest deals on Portland to Milwaukee flight tickets
Southwest
Sep 5
PDX6:00 amPortland
11h 50m
1 stop
MKE7:50 pmMilwaukee-Mitchell
Sep 11
MKE6:20 pmMilwaukee-Mitchell
7h 00m
1 stop
PDX11:20 pmPortland
$269
Southwest
Sep 5
PDX6:00 amPortland
11h 50m
1 stop
MKE7:50 pmMilwaukee-Mitchell
Sep 11
MKE5:45 amMilwaukee-Mitchell
15h 30m
2 stops
PDX7:15 pmPortland
$280
Southwest
Sep 11
PDX1:30 pmPortland
5h 55m
1 stop
MKE9:25 pmMilwaukee-Mitchell
Sep 14
MKE6:25 pmMilwaukee-Mitchell
7h 20m
1 stop
PDX11:45 pmPortland
$288

American Airlines flights from Portland to Milwaukee

Our best American Airlines deals on Portland to Milwaukee flight tickets
American Airlines
Sep 11
PDX5:10 amPortland
6h 55m
1 stop
MKE2:05 pmMilwaukee-Mitchell
Sep 16
MKE12:22 pmMilwaukee-Mitchell
8h 58m
1 stop
PDX7:20 pmPortland
$332
American Airlines
Oct 21
PDX5:20 amPortland
9h 37m
1 stop
MKE4:57 pmMilwaukee-Mitchell
Oct 31
MKE7:45 amMilwaukee-Mitchell
6h 37m
1 stop
PDX12:22 pmPortland
$347
American Airlines
Sep 24
PDX11:08 pmPortland
6h 53m
1 stop
MKE8:01 amMilwaukee-Mitchell
Oct 1
MKE5:22 pmMilwaukee-Mitchell
7h 50m
1 stop
PDX11:12 pmPortland
$348

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 August 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 Portland - MKE Milwaukee-Mitchell

PDXMKE

Portland

Sat 9/5

6:00 am-7:50 pm

1 stop11h 50m

Milwaukee-Mitchell

Fri 9/11

6:20 pm-11:20 pm

1 stop7h 00m

$269

PortlandMilwaukee

PDX Portland - MKE Milwaukee-Mitchell

PDXMKE

Portland

Sat 9/5

6:00 am-7:50 pm

1 stop11h 50m

Milwaukee-Mitchell

Fri 9/11

5:45 am-7:15 pm

2 stops15h 30m

$280

PortlandMilwaukee

PDX Portland - MKE Milwaukee-Mitchell

PDXMKE

Portland

Wed 9/23

11:35 am-9:09 pm

1 stop7h 34m

Milwaukee-Mitchell

Tue 9/29

6:30 am-12:37 pm

1 stop8h 07m

$311

PortlandMilwaukee

PDX Portland - MKE Milwaukee-Mitchell

PDXMKE

Portland

Thu 10/15

11:12 pm-8:39 am

1 stop7h 27m

Milwaukee-Mitchell

Wed 10/21

2:59 pm-9:40 pm

1 stop8h 41m

$311

PortlandMilwaukee

PDX Portland - MKE Milwaukee-Mitchell

PDXMKE

Portland

Thu 9/10

11:08 pm-8:01 am

1 stop6h 53m

Milwaukee-Mitchell

Mon 9/14

5:43 pm-11:23 pm

1 stop7h 40m

$311

PortlandMilwaukee

PDX Portland - MKE Milwaukee-Mitchell

PDXMKE

Portland

Wed 10/28

11:58 am-9:52 pm

1 stop7h 54m

Milwaukee-Mitchell

Thu 11/5

7:40 am-12:33 pm

1 stop6h 53m

$311
Quickest round-trip

PortlandMilwaukee

PDX Portland - MKE Milwaukee-Mitchell

PDXMKE

Portland

Fri 9/11

8:15 am-5:30 pm

1 stop7h 15m

Milwaukee-Mitchell

Wed 9/16

5:00 am-9:29 am

1 stop6h 29m

$314

PortlandMilwaukee

PDX Portland - MKE Milwaukee-Mitchell

PDXMKE

Portland

Sat 9/12

8:40 am-5:08 pm

1 stop6h 28m

Milwaukee-Mitchell

Fri 9/18

3:52 pm-10:52 pm

1 stop9h 00m

$355

PortlandMilwaukee

PDX Portland - MKE Milwaukee-Mitchell

PDXMKE

Portland

Tue 10/27

7:09 am-4:19 pm

1 stop7h 10m

Milwaukee-Mitchell

Tue 11/3

4:31 pm-9:43 am

2 stops19h 12m

$393

PortlandMilwaukee

PDX Portland - MKE Milwaukee-Mitchell

PDXMKE

Portland

Tue 12/8

5:00 am-1:52 pm

1 stop6h 52m

Milwaukee-Mitchell

Thu 12/10

2:55 pm-12:10 am

2 stops11h 15m

$416

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?

Prices are currently low for flights on this route.

Typical prices usually range from $344 to $536.
The lowest price recently found on this route was $269.

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 $396.

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 $468 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 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 August 2026, prices for Portland to Milwaukee flights are approximately 3% cheaper 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 55m

Direct flights

None
The fastest flight from Portland to Milwaukee takes 5h 55m
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 55m.

  • 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
American AirlinesPriceFrom $209Free CancellationRating
7.1
11,915 reviews
Search American Airlines flights
DeltaPriceFrom $211Free CancellationRating
7.8
8,505 reviews
Search Delta flights
United AirlinesPriceFrom $278Free CancellationRating
7.4
10,113 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $304Free CancellationRating
7.9
12,800 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $322Free CancellationRating
8.0
4,218 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
West Bend
Port Washington
Kohler
Pewaukee
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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