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$128+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
Aug 13 — Aug 201
Thu 8/13
Thu 8/20
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 July 14, 2026.

This Delta deal was found by Cheapflights users on 7/8. 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 8/512:35 am
PDX
-
MKE
1 stop6h 05m
Delta
Mon 8/103:01 pm
MKE
-
PDX
1 stop8h 43m
Delta
Deal found 7/8$255
This Southwest deal was found by Cheapflights users on 7/9. 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.
Mon 10/58:00 am
PDX
-
MKE
1 stop9h 25m
Southwest
Thu 10/810:25 am
MKE
-
PDX
2 stops14h 40m
Southwest
Deal found 7/9$266
This United Airlines deal was found by Cheapflights users on 7/9. 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.
Sat 8/1511:02 pm
PDX
-
MKE
1 stop6h 05m
United Airlines
Wed 8/195:00 am
MKE
-
PDX
1 stop6h 29m
United Airlines
Deal found 7/9$280
This Southwest deal was found by Cheapflights users on 7/9. 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.
Thu 9/248:00 am
PDX
-
MKE
1 stop7h 00m
Southwest
Mon 9/284:20 pm
MKE
-
PDX
1 stop6h 25m
Southwest
Deal found 7/9$281
This United Airlines deal was found by Cheapflights users on 7/9. 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.
Thu 8/610:40 pm
PDX
-
MKE
1 stop6h 20m
United Airlines
Thu 8/135:00 am
MKE
-
PDX
1 stop6h 29m
United Airlines
Deal found 7/9$293
This United Airlines deal was found by Cheapflights users on 7/10. 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.
Sat 9/2612:45 pm
PDX
-
MKE
2 stops8h 14m
United Airlines
Wed 9/305:00 am
MKE
-
PDX
1 stop6h 31m
United Airlines
Deal found 7/10$303
This United Airlines deal was found by Cheapflights users on 7/13. 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.
Sat 9/55:00 am
PDX
-
MKE
1 stop6h 29m
United Airlines
Fri 9/115:00 am
MKE
-
PDX
1 stop6h 29m
United Airlines
Deal found 7/13$307
This Southwest deal was found by Cheapflights users on 7/13. 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.
Sat 9/59:00 am
PDX
-
MKE
1 stop8h 45m
Southwest
Fri 9/115:45 am
MKE
-
PDX
2 stops11h 15m
Southwest
Deal found 7/13$312
This Southwest deal was found by Cheapflights users on 7/13. 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.
Tue 9/155:50 am
PDX
-
MKE
1 stop8h 50m
Southwest
Tue 9/225:00 pm
MKE
-
PDX
1 stop6h 55m
Southwest
Deal found 7/13$317
This American Airlines deal was found by Cheapflights users on 7/11. 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.
Tue 8/1811:34 pm
PDX
-
MKE
1 stop6h 15m
American Airlines
Tue 8/2512:28 pm
MKE
-
PDX
1 stop8h 31m
American Airlines
Deal found 7/11$319

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 July 14, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$255
(Delta)

One-way from

$128
(Delta)

Popular in

June

Cheapest in

January

Average price

$558
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. 12% potential increase in price ($66 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 14, 2026.
Use the filters below to find and compare flights from Portland to Milwaukee that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Fri 8/7

11:20 pm-8:45 am

1 stop7h 25m

Milwaukee-Mitchell

Fri 8/14

4:47 pm-10:09 pm

1 stop7h 22m

$255

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Fri 9/4

2:27 pm-10:36 pm

1 stop6h 09m

Milwaukee-Mitchell

Tue 9/8

5:00 am-9:29 am

1 stop6h 29m

$255
Quickest round-trip

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Sat 8/15

11:02 pm-7:07 am

1 stop6h 05m

Milwaukee-Mitchell

Wed 8/19

5:00 am-9:29 am

1 stop6h 29m

$280

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Sat 8/22

7:16 am-3:47 pm

1 stop6h 31m

Milwaukee-Mitchell

Tue 8/25

6:15 am-11:28 am

1 stop7h 13m

$355

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Tue 9/29

12:57 pm-10:45 pm

1 stop7h 48m

Milwaukee-Mitchell

Wed 9/30

10:42 am-3:56 pm

1 stop7h 14m

$355

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Wed 8/5

12:35 am-8:40 am

1 stop6h 05m

Milwaukee-Mitchell

Wed 8/12

12:51 pm-6:55 pm

1 stop8h 04m

$368

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Wed 8/26

11:35 am-9:25 pm

2 stops7h 50m

Milwaukee-Mitchell

Sun 8/30

5:45 am-2:05 pm

2 stops10h 20m

$402

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Sat 8/8

10:59 pm-7:49 am

1 stop6h 50m

Milwaukee-Mitchell

Tue 8/11

1:17 pm-11:59 pm

2 stops12h 42m

$410

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Fri 9/11

11:09 pm-10:29 am

1 stop9h 20m

Milwaukee-Mitchell

Wed 9/16

2:20 pm-10:45 pm

2 stops10h 25m

$417

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Thu 9/10

5:00 am-1:34 pm

1 stop6h 34m

Milwaukee-Mitchell

Tue 9/15

2:20 pm-10:45 pm

2 stops10h 25m

$422

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/10

Showing 1-10 of 18 resultsSorted by cheapest first
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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*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?

Booking 34 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, January is the cheapest month in which you can book a flight from Portland to Milwaukee (average of $324). Flying from Portland to Milwaukee in June is currently the most expensive (average of $576). 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 July 14, 2026.
Read through reviews of airlines operating flights from Portland to Milwaukee, such as Southwest,Alaska Airlines, andDelta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
Alaska Airlines
7.9
Good
12,652 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
Delta
7.8
Good
8,467 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
United Airlines
7.4
Good
9,990 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
American Airlines
7.1
Good
11,808 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.

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 6h 09m. 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 United Airlines. According to our data, you can fly for as low as $118. Users have also found prices from $138 and $139 on American Airlines and Delta, 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, January is the cheapest month in which you can book a flight from Portland to Milwaukee (average of $324). Flying from Portland to Milwaukee in June is currently the most expensive (average of $576). 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
Port Washington
New Berlin
Oak Creek
Wauwatosa

Browse thousands of different options on Cheapflights for your next trip

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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 July 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$88Average$415FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$209Average$478FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$278Average$451FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$304Average$406FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$324Average$536FlexibilityNo cancel feeOn-time63%

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