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$126+ 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. 6 — feb. 131
vie. 2/6
vie. 2/13
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 enero 7, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$247
(United Airlines)

One-way from

$126
(United Airlines)

Popular in

March

Cheapest in

January

Average price

$333
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 enero 7, 2026.

This United Airlines deal was found by Cheapflights users on 1/5. 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.
mar. 2/241:18 pmPDX - MKE
1 stop5h 48mUnited Airlines
mié. 2/256:00 amMKE - PDX
1 stop7h 55mUnited Airlines
Deal found 1/5$247
This United Airlines deal was found by Cheapflights users on 1/7. 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.
mié. 2/111:24 pmPDX - MKE
1 stop5h 57mUnited Airlines
mar. 2/176:00 amMKE - PDX
1 stop7h 55mUnited Airlines
Deal found 1/7$251
This Delta deal was found by Cheapflights users on 1/7. 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.
mié. 2/117:37 pmPDX - MKE
2 stops11h 14mDelta
mar. 2/176:15 amMKE - PDX
2 stops8h 27mDelta
Deal found 1/7$254
This Delta deal was found by Cheapflights users on 1/6. 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.
mié. 2/116:00 amPDX - MKE
1 stop7h 13mDelta
sáb. 2/143:53 pmMKE - PDX
2 stops8h 55mDelta
Deal found 1/6$272
This Alaska Airlines deal was found by Cheapflights users on 1/6. 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.
vie. 2/67:10 amPDX - MKE
1 stop5h 47mAlaska Airlines
dom. 2/84:03 pmMKE - PDX
1 stop26h 31mAlaska Airlines
Deal found 1/6$283
This Delta deal was found by Cheapflights users on 1/6. 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.
vie. 2/277:35 pmPDX - MKE
2 stops12h 55mDelta
jue. 3/51:21 pmMKE - PDX
2 stops9h 34mDelta
Deal found 1/6$284
This Southwest deal was found by Cheapflights users on 1/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 2/99:25 amPDX - MKE
1 stop12h 25mSouthwest
mié. 2/115:10 amMKE - PDX
1 stop7h 25mSouthwest
Deal found 1/5$285
This Delta deal was found by Cheapflights users on 1/5. 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.
sáb. 1/317:10 amPDX - MKE
2 stops12h 05mDelta
vie. 2/67:45 amMKE - PDX
2 stops13h 05mDelta
Deal found 1/5$290
This American Airlines deal was found by Cheapflights users on 1/6. 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.
mié. 2/116:00 amPDX - MKE
1 stop7h 57mAmerican Airlines
sáb. 2/144:47 pmMKE - PDX
1 stop9h 30mAmerican Airlines
Deal found 1/6$294

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 enero 7, 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

mar. 2/24

1:18 pm-9:06 pm

1 stop5h 48m

Milwaukee-Mitchell

mié. 2/25

6:00 am-11:55 am

1 stop7h 55m

$247

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

mié. 2/11

1:24 pm-9:21 pm

1 stop5h 57m

Milwaukee-Mitchell

mar. 2/17

6:00 am-11:55 am

1 stop7h 55m

$251

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

mié. 2/11

7:37 pm-8:51 am

2 stops11h 14m

Milwaukee-Mitchell

mar. 2/17

6:15 am-12:42 pm

2 stops8h 27m

$254

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

mié. 2/11

6:00 am-3:13 pm

1 stop7h 13m

Milwaukee-Mitchell

sáb. 2/14

3:53 pm-10:48 pm

2 stops8h 55m

$272

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

vie. 2/27

7:05 am-2:51 pm

1 stop5h 46m

Milwaukee-Mitchell

jue. 3/5

3:47 pm-8:49 am

1 stop19h 02m

$283

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

vie. 2/6

7:10 am-2:57 pm

1 stop5h 47m

Milwaukee-Mitchell

dom. 2/8

4:03 pm-10:46 pm

1 stop8h 43m

$283

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

lun. 2/9

9:25 am-11:50 pm

1 stop12h 25m

Milwaukee-Mitchell

mié. 2/11

5:10 am-10:35 am

1 stop7h 25m

$285

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

sáb. 1/31

7:10 am-9:15 pm

2 stops12h 05m

Milwaukee-Mitchell

vie. 2/6

7:45 am-6:50 pm

2 stops13h 05m

$290

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

mar. 3/10

12:04 pm-11:18 pm

1 stop9h 14m

$126

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

mié. 3/11

6:05 am-3:16 pm

1 stop7h 11m

$126

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Showing 1-10 of 18 results
1
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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
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Portland-Milwaukee flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 2, 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 March is currently the most expensive (average of $248). 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 enero 7, 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
11,661 reviews

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
Alaska Airlines
8.0
Very good
11,661 reviews
Alaska Airlines
8.0
Very good
11,661 reviews

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
Southwest
8.0
Very good
4,250 reviews
Alaska Airlines
8.0
Very good
11,661 reviews

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
Delta
7.9
Good
8,025 reviews
Alaska Airlines
8.0
Very good
11,661 reviews

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
United Airlines
7.4
Good
9,139 reviews
Alaska Airlines
8.0
Very good
11,661 reviews

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
American Airlines
7.2
Good
11,095 reviews
Alaska Airlines
8.0
Very good
11,661 reviews

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.

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 48m. 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 $153 and $169 on American Airlines and Alaska 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 March is currently the most expensive (average of $248). 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 enero 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$176Average$439FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$209Average$405FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$304Average$414FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$307Average$458FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$341Average$510FlexibilityNo cancel feeOn-time63%

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