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$82+ 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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Milwaukee-Mitchell are usually found in April or January, booked 35 days in advance, depart on a Tuesday or Thursday and return on a Wednesday

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 August 18, 2025.

Round-trip from

$170
(Expedia)

One-way from

$82
(Priceline)

Popular in

March

Cheapest in

April

Average price

$389
From Portland to Milwaukee-Mitchell
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One-way flight from Portland to Milwaukee-Mitchell
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Highest demand for flights based on searches. 0% potential increase in price ($3 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 August 18, 2025.

This Expedia deal was found by Cheapflights users on 8/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/156:05 amPDX - MKE
1 stop11h 14mFrontier
Mon 9/298:04 pmMKE - PDX
1 stop6h 08mFrontier
Deal found 8/18$170
This Priceline deal was found by Cheapflights users on 8/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/266:05 amPDX - MKE
1 stop10h 36mFrontier
Sun 9/283:03 pmMKE - PDX
1 stop11h 09mFrontier
Deal found 8/17$187
This Orbitz deal was found by Cheapflights users on 8/17. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/196:05 amPDX - MKE
1 stop10h 36mFrontier
Mon 9/228:04 pmMKE - PDX
1 stop6h 08mFrontier
Deal found 8/17$206
This Justfly.com deal was found by Cheapflights users on 8/17. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/266:05 amPDX - MKE
1 stop10h 36mMultiple Airlines
Sun 9/289:50 pmMKE - PDX
1 stop15h 21mMultiple Airlines
Deal found 8/17$237
This Trip.com deal was found by Cheapflights users on 8/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/152:32 pmPDX - MKE
1 stop7h 30mMultiple Airlines
Mon 9/228:04 pmMKE - PDX
1 stop6h 08mMultiple Airlines
Deal found 8/16$238
This Orbitz deal was found by Cheapflights users on 8/18. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/112:32 pmPDX - MKE
1 stop7h 30mMultiple Airlines
Mon 9/158:04 pmMKE - PDX
1 stop6h 08mMultiple Airlines
Deal found 8/18$249
This Orbitz deal was found by Cheapflights users on 8/16. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/196:05 amPDX - MKE
1 stop10h 36mMultiple Airlines
Tue 9/236:27 amMKE - PDX
1 stop9h 20mMultiple Airlines
Deal found 8/16$266
This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/912:43 pmPDX - MKE
1 stop28h 35mFrontier
Mon 10/138:04 pmMKE - PDX
1 stop17h 44mFrontier
Deal found 8/17$270
This Orbitz deal was found by Cheapflights users on 8/17. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/126:00 amPDX - MKE
1 stop7h 00mMultiple Airlines
Mon 11/1711:32 amMKE - PDX
1 stop12h 04mMultiple Airlines
Deal found 8/17$272
This Hawaiian Airlines deal was found by Cheapflights users on 8/18. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/132:32 pmPDX - MKE
1 stop7h 30mHawaiian Airlines
Tue 9/166:27 amMKE - PDX
1 stop8h 00mHawaiian Airlines
Deal found 8/18$278
This Delta deal was found by Cheapflights users on 8/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1212:45 amPDX - MKE
1 stop8h 12mDelta
Tue 9/164:00 pmMKE - PDX
1 stop6h 56mDelta
Deal found 8/18$279
This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1612:43 pmPDX - MKE
1 stop28h 35mMultiple Airlines
Sun 10/197:32 pmMKE - PDX
1 stop18h 10mMultiple Airlines
Deal found 8/17$281

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 August 18, 2025.
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

Mon 9/15

6:05 am-7:19 pm

1 stop11h 14m

Milwaukee-Mitchell

Mon 9/29

8:04 pm-12:12 am

1 stop6h 08m

$170

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Fri 9/26

6:05 am-6:41 pm

1 stop10h 36m

Milwaukee-Mitchell

Sun 9/28

3:03 pm-12:12 am

1 stop11h 09m

$187

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Fri 9/19

6:05 am-6:41 pm

1 stop10h 36m

Milwaukee-Mitchell

Mon 9/22

8:04 pm-12:12 am

1 stop6h 08m

$206

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Fri 9/26

6:05 am-6:41 pm

1 stop10h 36m

Milwaukee-Mitchell

Sun 9/28

9:50 pm-11:11 am

1 stop15h 21m

$237

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Mon 9/15

2:32 pm-12:02 am

1 stop7h 30m

Milwaukee-Mitchell

Mon 9/22

8:04 pm-12:12 am

1 stop6h 08m

$238

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Thu 9/11

2:32 pm-12:02 am

1 stop7h 30m

Milwaukee-Mitchell

Mon 9/15

8:04 pm-12:12 am

1 stop6h 08m

$249

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Sat 9/27

6:05 am-2:24 pm

1 stop6h 19m

Milwaukee-Mitchell

Sun 9/28

3:03 pm-12:12 am

1 stop11h 09m

$266

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Fri 9/19

6:05 am-6:41 pm

1 stop10h 36m

Milwaukee-Mitchell

Tue 9/23

6:27 am-1:47 pm

1 stop9h 20m

$266

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Thu 10/9

12:43 pm-7:18 pm

1 stop28h 35m

Milwaukee-Mitchell

Mon 10/13

8:04 pm-11:48 am

1 stop17h 44m

$270

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Wed 11/12

6:00 am-3:00 pm

1 stop7h 00m

Milwaukee-Mitchell

Mon 11/17

11:32 am-9:36 pm

1 stop12h 04m

$272

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 22 results
1
2
3

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 August 8, 2025.

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, February is the cheapest month in which you can book a flight from Portland to Milwaukee (average of $280). Flying from Portland to Milwaukee in June is currently the most expensive (average of $376). 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.

What is the cheapest time of day to fly from PDX to MKE?

Find hourly flight availability from Portland to Milwaukee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 18, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 9% on flights from Portland to Milwaukee by exploring options for tickets in the evening.

What is the cheapest day to fly from Portland to Milwaukee?

Use this chart to determine the cheapest time to fly round-trip from Portland to Milwaukee. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Portland to Milwaukee flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 August 18, 2025.
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
10,000 reviews

Overall

8.0

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.
Delta
8.0
Very good
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.
United Airlines
7.4
Good
8,925 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2025

PDX - SJC

They had no snacks and had to pay for the Wifi.

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 11h 14m. Airlines will cover a distance of 1712 mi.

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

    Spirit Airlines, at $58, was found to be the cheapest airline from Portland to Milwaukee.Alternate airlines to your destination round-trip include Frontier and Delta. Spirit Airlines is currently priced 86% below the average price you’ll pay for this route.

  • 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, February is the cheapest month in which you can book a flight from Portland to Milwaukee (average of $280). Flying from Portland to Milwaukee in June is currently the most expensive (average of $376). 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
Mequon
Oak Creek
Sheboygan
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 7 airlines flying from Portland to Milwaukee

Discover the top 7 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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$58Average$347FlexibilityNo cancel feeOn-time65%
FrontierCheapest$128Average$261FlexibilityNo cancel feeOn-time62%
DeltaCheapest$177Average$441FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$286Average$432FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$305Average$456FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$326Average$450FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$361Average$520FlexibilityNo cancel feeOn-time63%

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