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$106+ 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 6/30. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MKE
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
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 37 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 June 16, 2025.

Round-trip from

$332
(Mytrip)

One-way from

$106
(Priceline)

Popular in

December

Cheapest in

April

Average price

$521
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, 3% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 16, 2025.

This Mytrip deal was found by Cheapflights users on 6/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/812:12 pmPDX - MKE
3 stops25h 30mSpirit Airlines
Thu 7/102:51 pmMKE - PDX
1 stop20h 27mSpirit Airlines
Deal found 6/14$332
This American Airlines deal was found by Cheapflights users on 6/14. 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 8/1411:59 pmPDX - MKE
1 stop8h 31mAmerican Airlines
Mon 8/185:48 pmMKE - PDX
1 stop7h 11mAmerican Airlines
Deal found 6/14$335
This Delta deal was found by Cheapflights users on 6/15. 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 8/136:20 amPDX - MKE
1 stop6h 49mDelta
Wed 8/207:30 amMKE - PDX
2 stops11h 29mDelta
Deal found 6/15$337
This Frontier deal was found by Cheapflights users on 6/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/156:35 amPDX - MKE
1 stop10h 38mFrontier
Mon 8/187:58 pmMKE - PDX
1 stop6h 18mFrontier
Deal found 6/14$345
This Alaska Airlines deal was found by Cheapflights users on 6/15. 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.
Sat 7/51:20 pmPDX - MKE
1 stop8h 39mAlaska Airlines
Wed 7/96:30 amMKE - PDX
1 stop7h 50mAlaska Airlines
Deal found 6/15$346
This United Airlines deal was found by Cheapflights users on 6/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/2711:59 pmPDX - MKE
1 stop8h 03mUnited Airlines
Tue 8/57:00 amMKE - PDX
1 stop6h 43mUnited Airlines
Deal found 6/16$348
This Mytrip deal was found by Cheapflights users on 6/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/311:59 pmPDX - MKE
1 stop13h 36mMultiple Airlines
Thu 7/105:56 pmMKE - PDX
2 stops22h 19mMultiple Airlines
Deal found 6/16$349
This Sun Country Air deal was found by Cheapflights users on 6/14. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/236:10 pmPDX - MKE
1 stop21h 19mSun Country Air
Sun 7/276:24 pmMKE - PDX
1 stop6h 22mSun Country Air
Deal found 6/14$350
This Southwest deal was found by Cheapflights users on 6/15. 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 8/145:00 amPDX - MKE
2 stops9h 15mSouthwest
Mon 8/187:55 amMKE - PDX
2 stops14h 15mSouthwest
Deal found 6/15$351
This Hawaiian Airlines deal was found by Cheapflights users on 6/16. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/121:24 pmPDX - MKE
1 stop8h 35mHawaiian Airlines
Thu 9/186:30 amMKE - PDX
1 stop7h 54mHawaiian Airlines
Deal found 6/16$361

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 June 16, 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 7/8

12:12 pm-3:42 pm

3 stops25h 30m

Milwaukee-Mitchell

Thu 7/10

2:51 pm-9:18 am

1 stop20h 27m

$332

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Thu 8/14

11:59 pm-10:30 am

1 stop8h 31m

Milwaukee-Mitchell

Mon 8/18

5:48 pm-10:59 pm

1 stop7h 11m

$335

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Wed 8/13

6:20 am-3:09 pm

1 stop6h 49m

Milwaukee-Mitchell

Wed 8/20

7:30 am-4:59 pm

2 stops11h 29m

$337

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Fri 8/15

6:35 am-7:13 pm

1 stop10h 38m

Milwaukee-Mitchell

Mon 8/18

7:58 pm-12:16 am

1 stop6h 18m

$345

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Sat 7/5

1:20 pm-11:59 pm

1 stop8h 39m

Milwaukee-Mitchell

Wed 7/9

6:30 am-12:20 pm

1 stop7h 50m

$346

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Sun 7/27

11:59 pm-10:02 am

1 stop8h 03m

Milwaukee-Mitchell

Tue 8/5

7:00 am-11:43 am

1 stop6h 43m

$348

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Thu 7/3

11:59 pm-3:35 pm

1 stop13h 36m

Milwaukee-Mitchell

Thu 7/10

5:56 pm-2:15 pm

2 stops22h 19m

$349

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Wed 7/23

6:10 pm-5:29 pm

1 stop21h 19m

Milwaukee-Mitchell

Sun 7/27

6:24 pm-10:46 pm

1 stop6h 22m

$350

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Thu 8/14

5:00 am-4:15 pm

2 stops9h 15m

Milwaukee-Mitchell

Mon 8/18

7:55 am-8:10 pm

2 stops14h 15m

$351

PortlandMilwaukee

PDX - MKE

PDXMKE

Portland

Mon 6/30

6:35 am-7:11 pm

1 stop10h 36m

$106

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Showing 1-10 of 19 results
1
2

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 June 13, 2025.

Booking 37 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 June 16, 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.

Rainfall in Milwaukee by month

Plan your trip to Milwaukee by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Milwaukee ranges from 1.4 - 4.0 inches per month. June is typically the wettest month, when rainfall can reach 4.0 in. January is typically the driest time to visit Milwaukee when rainfall is around 1.4 in.

Temperature in Milwaukee by month

Plan your trip to Milwaukee by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Milwaukee, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 21.2 F).

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 June 16, 2025.
See what other customers who have flown with Alaska Airlines, Southwest and Delta from Portland to Milwaukee have to say. 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

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,278 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,963 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,500 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,801 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

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

    Spirit Airlines, at $332, was found to be the cheapest airline from Portland to Milwaukee.Alternate airlines to your destination round-trip include American Airlines and Delta. Spirit Airlines is currently priced 25% 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 Frontier. According to our data, you can fly for as low as $106. Users have also found prices from $123 and $139 on Spirit 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, 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 Portland?

Book flights to Portland if you plan to visit one of these locations
Mequon
Sheboygan
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 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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$58Average$228FlexibilityNo cancel feeOn-time65%
FrontierCheapest$128Average$254FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$286Average$426FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$305Average$471FlexibilityNo cancel feeOn-time75%
DeltaCheapest$317Average$448FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$326Average$469FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$362Average$514FlexibilityNo cancel feeOn-time63%

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