HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Milwaukee

$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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
Jan 1 — Jan 81
Thu 1/1
Thu 1/8
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Milwaukee with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Portland to Milwaukee-Mitchell are usually found in January or April, booked 35 days in advance, depart on a Tuesday or Thursday and return on a Wednesday

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 December 2, 2025.

This Delta deal was found by Cheapflights users on 11/30. 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 12/295:30 amPDX - MKE
2 stops9h 13mDelta
Fri 1/96:40 amMKE - PDX
2 stops14h 10mDelta
Deal found 11/30$276
This American Airlines deal was found by Cheapflights users on 12/2. 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.
Thu 12/255:33 amPDX - MKE
1 stop9h 31mAmerican Airlines
Sat 1/103:53 pmMKE - PDX
1 stop8h 18mAmerican Airlines
Deal found 12/2$301
This Kiwi.com deal was found by Cheapflights users on 11/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2711:59 pmPDX - MKE
1 stop15h 34mMultiple Airlines
Wed 1/73:10 pmMKE - PDX
2 stops22h 05mMultiple Airlines
Deal found 11/30$306
This Alaska Airlines deal was found by Cheapflights users on 12/2. 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.
Tue 12/302:56 pmPDX - MKE
1 stop7h 03mAlaska Airlines
Tue 1/63:05 pmMKE - PDX
1 stop8h 50mAlaska Airlines
Deal found 12/2$311
This Delta deal was found by Cheapflights users on 11/30. 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.
Sun 12/287:30 pmPDX - MKE
2 stops12h 57mDelta
Wed 1/711:03 amMKE - PDX
2 stops11h 56mDelta
Deal found 11/30$315
This Delta deal was found by Cheapflights users on 11/30. 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.
Thu 12/2512:16 pmPDX - MKE
1 stop7h 19mDelta
Sat 1/1011:03 amMKE - PDX
2 stops9h 47mDelta
Deal found 11/30$316
This Delta deal was found by Cheapflights users on 11/30. 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.
Wed 12/315:15 pmPDX - MKE
2 stops15h 13mDelta
Tue 1/63:59 pmMKE - PDX
2 stops10h 18mDelta
Deal found 11/30$317
This Delta deal was found by Cheapflights users on 11/30. 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 12/295:30 amPDX - MKE
2 stops9h 13mDelta
Tue 1/63:59 pmMKE - PDX
1 stop6h 13mDelta
Deal found 11/30$339

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 December 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$183
(American Airlines)

One-way from

$119
(American Airlines)

Popular in

March

Cheapest in

January

Average price

$476
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. 1% potential increase in price ($6 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 2, 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

Tue 1/6

1:53 pm-9:30 pm

1 stop5h 37m

Milwaukee-Mitchell

Tue 1/13

6:15 am-12:46 pm

1 stop8h 31m

$207

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Wed 2/11

6:00 am-3:13 pm

1 stop7h 13m

Milwaukee-Mitchell

Tue 2/17

7:20 am-12:25 pm

1 stop7h 05m

$207

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Mon 2/23

12:40 am-10:21 am

1 stop7h 41m

Milwaukee-Mitchell

Mon 3/2

11:01 am-8:55 pm

2 stops11h 54m

$221

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Wed 2/25

1:32 pm-9:32 pm

1 stop6h 00m

Milwaukee-Mitchell

Mon 3/2

11:01 am-8:55 pm

2 stops11h 54m

$221

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 2/24

1:27 pm-8:51 am

2 stops17h 24m

Milwaukee-Mitchell

Tue 3/3

11:01 am-5:33 pm

1 stop8h 32m

$221

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 1/27

6:15 am-3:19 pm

1 stop7h 04m

Milwaukee-Mitchell

Sat 1/31

3:59 pm-8:32 pm

1 stop6h 33m

$238

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Fri 2/27

7:35 pm-10:30 am

2 stops12h 55m

Milwaukee-Mitchell

Mon 3/2

11:01 am-6:48 pm

2 stops9h 47m

$238

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Sat 2/28

1:53 pm-9:34 pm

1 stop5h 41m

Milwaukee-Mitchell

Tue 3/3

11:01 am-5:33 pm

1 stop8h 32m

$238

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 1/13

7:10 am-9:30 pm

2 stops12h 20m

Milwaukee-Mitchell

Tue 1/27

7:45 am-12:32 pm

1 stop6h 47m

$241

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Mon 3/2

1:27 pm-8:51 am

2 stops17h 24m

Milwaukee-Mitchell

Tue 3/3

2:57 pm-8:30 pm

1 stop7h 33m

$241

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/1

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 December.
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 November 28, 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, 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 $243). 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 December 2, 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 Tuesday afternoons 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 December 2, 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
11,388 reviews

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.
Alaska Airlines
8.0
Very good
11,388 reviews
Alaska Airlines
8.0
Very good
11,388 reviews

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.
Southwest
8.0
Very good
4,253 reviews
Alaska Airlines
8.0
Very good
11,388 reviews

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.
Delta
7.9
Good
8,011 reviews
Alaska Airlines
8.0
Very good
11,388 reviews

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.
United Airlines
7.4
Good
9,063 reviews
Alaska Airlines
8.0
Very good
11,388 reviews

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.
American Airlines
7.2
Good
11,045 reviews
Alaska Airlines
8.0
Very good
11,388 reviews

Food

7.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2025

PDX - BNA

My family especially liked the leg room and comfortable seats.

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 37m. 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 80% 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 $142 and $163 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 $243). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Milwaukee

See prices for flight routes from nearby airports that may be better suited for you.
Portland to O'Hare Intl flights
Portland to Minneapolis flights
Boise to Minneapolis flights
Boise to O'Hare Intl flights
Portland to Appleton flights
Eugene to O'Hare Intl flights
Eugene to Minneapolis flights
Portland to Madison flights
Redmond to Minneapolis flights
Medford to Minneapolis flights
Medford to O'Hare Intl flights
Boise to Milwaukee flights
Eugene to Madison flights
Boise to Green Bay flights
Portland to Duluth flights
Portland to Green Bay flights
Boise to Appleton flights
Boise to Madison flights
Eugene to Milwaukee flights
Redmond to O'Hare Intl flights
Portland to Wausau flights
Redmond to Milwaukee flights
Yakima to O'Hare Intl flights
Boise to Wausau flights
Portland to Escanaba flights
Boise to Duluth flights
Medford to Milwaukee flights
Medford to Madison flights
Portland to La Crosse flights
Redmond to Appleton flights
Portland to Rhinelander flights
Redmond to Duluth flights
Redmond to Green Bay flights
Redmond to Rhinelander flights
Portland to Dubuque flights
Redmond to La Crosse flights
Eugene to Dubuque flights
Boise to La Crosse flights
North Bend to O'Hare Intl flights

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 December 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$176Average$437FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$254Average$414FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$307Average$456FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$324Average$421FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$341Average$514FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.