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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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 29, 2026.

This United Airlines deal was found by Cheapflights users on 1/27. 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 2/1710:38 pm
PDX
-
MKE
1 stop10h 20m
United Airlines
Sat 2/214:10 pm
MKE
-
PDX
1 stop7h 05m
United Airlines
Deal found 1/27$237
This United Airlines deal was found by Cheapflights users on 1/27. 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 2/241:18 pm
PDX
-
MKE
1 stop5h 48m
United Airlines
Tue 3/36:00 am
MKE
-
PDX
2 stops9h 44m
United Airlines
Deal found 1/27$242
This Delta deal was found by Cheapflights users on 1/28. 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.
Mon 4/277:32 pm
PDX
-
MKE
2 stops11h 18m
Delta
Wed 4/293:53 pm
MKE
-
PDX
1 stop6h 12m
Delta
Deal found 1/28$285
This Alaska Airlines deal was found by Cheapflights users on 1/27. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/18:30 pm
PDX
-
MKE
1 stop16h 13m
Alaska Airlines
Thu 5/77:00 am
MKE
-
PDX
1 stop7h 52m
Alaska Airlines
Deal found 1/27$293
This Delta deal was found by Cheapflights users on 1/26. 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 3/31:53 pm
PDX
-
MKE
1 stop5h 41m
Delta
Mon 3/164:48 pm
MKE
-
PDX
1 stop7h 05m
Delta
Deal found 1/26$297
This Delta deal was found by Cheapflights users on 1/27. 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 2/177:35 pm
PDX
-
MKE
2 stops11h 16m
Delta
Sat 2/216:15 am
MKE
-
PDX
1 stop8h 29m
Delta
Deal found 1/27$300
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Fri 2/2012:57 pm
PDX
-
MKE
1 stop7h 48m
United Airlines
Tue 2/247:00 am
MKE
-
PDX
1 stop6h 55m
United Airlines
Deal found 1/27$304
This Delta deal was found by Cheapflights users on 1/27. 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 2/247:15 am
PDX
-
MKE
2 stops12h 17m
Delta
Tue 3/37:30 am
MKE
-
PDX
2 stops13h 18m
Delta
Deal found 1/27$324
This United Airlines deal was found by Cheapflights users on 1/28. 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 3/44:10 pm
MKE
-
PDX
1 stop9h 04m
United Airlines
Deal found 1/28$327
This Alaska Airlines deal was found by Cheapflights users on 1/26. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/248:30 pm
PDX
-
MKE
1 stop16h 13m
Alaska Airlines
Mon 4/277:00 am
MKE
-
PDX
1 stop28h 31m
Alaska Airlines
Deal found 1/26$333

Find 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 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$237
(United Airlines)

One-way from

$119
(United Airlines)

Popular in

March

Cheapest in

January

Average price

$341
Provider with most accurate pricing for Portland-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Milwaukee-Mitchell flights.
Search Deals
From Portland to Milwaukee-Mitchell
Search Deals
One-way flight from Portland to Milwaukee-Mitchell
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($12 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 29, 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 3/3

11:59 pm-10:30 am

1 stop8h 31m

Milwaukee-Mitchell

Tue 3/10

1:25 pm-7:14 pm

1 stop7h 49m

$237

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 3/3

1:53 pm-9:34 pm

1 stop5h 41m

Milwaukee-Mitchell

Mon 3/16

4:48 pm-9:53 pm

1 stop7h 05m

$297

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 3/3

12:40 am-10:21 am

1 stop7h 41m

Milwaukee-Mitchell

Mon 3/16

4:48 pm-9:53 pm

1 stop7h 05m

$297

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Mon 4/27

11:59 pm-10:00 am

1 stop8h 01m

Milwaukee-Mitchell

Wed 4/29

3:52 pm-10:58 pm

1 stop9h 06m

$297

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 3/3

6:00 am-2:17 pm

1 stop6h 17m

Milwaukee-Mitchell

Sun 3/15

6:30 am-12:48 pm

1 stop8h 18m

$304

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 3/3

11:59 pm-10:30 am

1 stop8h 31m

Milwaukee-Mitchell

Sun 3/15

6:00 am-11:51 am

1 stop7h 51m

$304

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 3/3

12:40 am-10:21 am

1 stop7h 41m

Milwaukee-Mitchell

Sun 3/15

6:30 am-12:48 pm

1 stop8h 18m

$304

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Fri 2/20

1:18 pm-9:06 pm

1 stop5h 48m

Milwaukee-Mitchell

Tue 3/3

6:00 am-1:44 pm

2 stops9h 44m

$309

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 3/3

11:59 pm-10:30 am

1 stop8h 31m

Milwaukee-Mitchell

Wed 3/4

4:10 pm-11:14 pm

1 stop9h 04m

$327

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 3/10

6:05 am-3:16 pm

1 stop7h 11m

$119

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 21 results
1
2
3

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 Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 FlightHub the most. FlightHub 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 23, 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.

How much does it cost to fly round-trip from Portland to Milwaukee?

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 29, 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
11,807 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Boarding

8.1

Crew

8.5

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
11,807 reviews
Alaska Airlines
8.0
Very good
11,807 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Boarding

8.1

Crew

8.5

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
4,267 reviews
Alaska Airlines
8.0
Very good
11,807 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Boarding

8.1

Crew

8.5

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
8,128 reviews
Alaska Airlines
8.0
Very good
11,807 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Boarding

8.1

Crew

8.5

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
9,215 reviews
Alaska Airlines
8.0
Very good
11,807 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Boarding

8.1

Crew

8.5

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
11,205 reviews
Alaska Airlines
8.0
Very good
11,807 reviews

Comfort

7.8

Entertainment

7.0

Food

7.1

Boarding

8.1

Crew

8.5

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 5h 41m. 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 United 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 $150 on Southwest and United 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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Alternative routes for Portland to Milwaukee

See prices for flight routes from nearby airports that may be better suited for you.
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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 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$88Average$430FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$209Average$381FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$307Average$459FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$324Average$416FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$339Average$514FlexibilityNo cancel feeOn-time63%

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