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$119+ Cheap flights from Portland to Milwaukee (PDX - MKE)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
Feb 17 — Feb 241
Tue 2/17
Tue 2/24
1 adult, Economy
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Cheap flight deals from Portland to Milwaukee

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to Milwaukee (MKE). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$237
(United Airlines)

One-way from

$119
(American Airlines)

Popular in

March

Cheapest in

January

Average price

$341
Provider with most accurate pricing for Portland-Milwaukee-Mitchell flight deals.
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Provider most trusted by Cheapflights users for Portland-Milwaukee-Mitchell flights.
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From Portland to Milwaukee-Mitchell
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One-way flight from Portland to Milwaukee-Mitchell
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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Portland to Milwaukee

Cheapest flights from Portland to Milwaukee
Explore the most affordable flight options available from Portland to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 18, 2026.

This United Airlines deal was found by Cheapflights users on 1/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/105:00 am
PDX
-
MKE
1 stop6h 30m
United Airlines
Sat 2/146:00 am
MKE
-
PDX
1 stop7h 55m
United Airlines
Deal found 1/18$237
This Delta deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1012:40 am
PDX
-
MKE
1 stop7h 43m
Delta
Sat 2/143:53 pm
MKE
-
PDX
2 stops8h 55m
Delta
Deal found 1/16$300
This United Airlines deal was found by Cheapflights users on 1/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/115:00 am
PDX
-
MKE
1 stop6h 30m
United Airlines
Sun 2/154:10 pm
MKE
-
PDX
1 stop7h 05m
United Airlines
Deal found 1/18$304
This Delta deal was found by Cheapflights users on 1/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3111:15 pm
PDX
-
MKE
1 stop7h 35m
Delta
Fri 4/33:59 pm
MKE
-
PDX
2 stops10h 00m
Delta
Deal found 1/17$312
This United Airlines deal was found by Cheapflights users on 1/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/155:00 am
PDX
-
MKE
1 stop7h 27m
United Airlines
Sun 4/197:50 am
MKE
-
PDX
1 stop9h 19m
United Airlines
Deal found 1/18$323
This United Airlines deal was found by Cheapflights users on 1/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/35:05 am
PDX
-
MKE
1 stop7h 52m
United Airlines
Wed 3/411:30 am
MKE
-
PDX
1 stop9h 19m
United Airlines
Deal found 1/17$327
This American Airlines deal was found by Cheapflights users on 1/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/1611:40 pm
PDX
-
MKE
1 stop9h 21m
American Airlines
Mon 2/235:00 am
MKE
-
PDX
1 stop7h 58m
American Airlines
Deal found 1/17$337
This United Airlines deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1111:05 pm
PDX
-
MKE
2 stops13h 00m
United Airlines
Sat 2/1411:30 am
MKE
-
PDX
2 stops13h 36m
United Airlines
Deal found 1/16$338

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated January 18, 2026.
Use the filters below to find and compare flights from Portland to Milwaukee that are best for you.

Fly from

Portland

Fly to

Milwaukee

Route

Depart

Return

Price

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 2/10

12:59 pm-10:59 pm

1 stop8h 00m

Milwaukee-Mitchell

Sat 2/14

11:30 am-6:49 pm

1 stop9h 19m

$237

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 2/10

12:40 am-10:23 am

1 stop7h 43m

Milwaukee-Mitchell

Sat 2/14

3:53 pm-10:48 pm

2 stops8h 55m

$300

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 3/31

5:00 am-2:28 pm

1 stop7h 28m

Milwaukee-Mitchell

Fri 4/3

6:50 am-11:41 am

1 stop6h 51m

$304

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Wed 2/11

5:00 am-1:30 pm

1 stop6h 30m

Milwaukee-Mitchell

Sun 2/15

4:10 pm-9:15 pm

1 stop7h 05m

$304

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 3/31

11:15 pm-8:50 am

1 stop7h 35m

Milwaukee-Mitchell

Fri 4/3

3:59 pm-11:59 pm

2 stops10h 00m

$312

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 3/3

10:38 pm-10:58 am

1 stop10h 20m

Milwaukee-Mitchell

Wed 3/4

4:10 pm-11:14 pm

1 stop9h 04m

$327

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 3/10

2:05 pm-11:18 pm

1 stop7h 13m

$119

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Wed 2/11

1:39 pm-9:15 pm

1 stop5h 36m

$119

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 2/10

6:00 am-3:57 pm

1 stop7h 57m

$119

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 2/10

8:30 am-8:48 pm

2 stops10h 18m

$124

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

Showing 1-10 of 13 results
1
2

Compare providers for flights from Portland to Milwaukee

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Portland to Milwaukee in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
JustAirTicketPrice Accuracy-Trust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Portland-Milwaukee flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Milwaukee flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-Milwaukee flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland-Milwaukee flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Portland-Milwaukee flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Portland to Milwaukee

Have a flexible travel schedule? Discover the best time to fly to Milwaukee from Portland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Portland to Milwaukee

How far ahead should I book a flight from Portland to Milwaukee?

Use this chart to determine the optimal time to book a round-trip flight from Portland to Milwaukee. Price data was last updated on January 9, 2026.

Booking 35 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland to Milwaukee. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Portland to Milwaukee?

Currently, August is the cheapest month in which you can book a flight from Portland to Milwaukee (average of $88). Flying from Portland to Milwaukee in July is currently the most expensive (average of $237). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Milwaukee

Get insights into the airlines that provide service to Milwaukee. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Milwaukee. Reviews last updated January 18, 2026.
Read through reviews of airlines operating flights from Portland to Milwaukee, such as Alaska Airlines, Southwest, and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,737 reviews

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Alaska Airlines
8.0
Very good
11,737 reviews
Alaska Airlines
8.0
Very good
11,737 reviews

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Southwest
8.0
Very good
4,261 reviews
Alaska Airlines
8.0
Very good
11,737 reviews

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Delta
7.9
Good
8,075 reviews
Alaska Airlines
8.0
Very good
11,737 reviews

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
United Airlines
7.4
Good
9,174 reviews
Alaska Airlines
8.0
Very good
11,737 reviews

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
American Airlines
7.2
Good
11,155 reviews
Alaska Airlines
8.0
Very good
11,737 reviews

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

Related info for your journey

Find useful and relevant information for your journey from Portland to Milwaukee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Portland to Milwaukee?

    Departing from Portland to Milwaukee will take you 7h 43m. Airlines will cover a distance of 1712 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Portland to Milwaukee round-trip?

    Delta, at $88, was found to be the cheapest airline from Portland to Milwaukee.Alternate airlines to your destination round-trip include American Airlines and Alaska Airlines. Delta is currently priced 79% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Portland to Milwaukee one-way?

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $139. Users have also found prices from $139 and $153 on Southwest and American Airlines, respectively.

  • Can I find deals for flights from Portland to Milwaukee that include hotel bookings?

    Yes. In addition to deals on Portland to Milwaukee flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Milwaukee?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Milwaukee.

  • Can I find deals for business class flights from Portland to Milwaukee?

    Yes. Cheapflights offers flight deals from Portland to Milwaukee by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Portland to Milwaukee?

    Currently, August is the cheapest month in which you can book a flight from Portland to Milwaukee (average of $88). Flying from Portland to Milwaukee in July is currently the most expensive (average of $237). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Milwaukee?

Book flights to Milwaukee if you plan to visit one of these locations
Sheboygan
New Berlin
Oak Creek
Wauwatosa

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Top 5 airlines flying from Portland to Milwaukee

Discover the top 5 airlines that operate flights from Portland to Milwaukee. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$88Average$431FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$209Average$402FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$304Average$406FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$307Average$454FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$341Average$508FlexibilityNo cancel feeOn-time63%

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