$136 Cheap Flights from Portland (PWM) to Milwaukee (MKE)

View $136 flight on Wed, Jul 2, 2025Opens in a new window

Popular airlines from Portland Intl. Jetport Airport (PWM) to General Mitchell Intl. Airport (MKE)

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Find available prices by choosing your travel dates.

Cheap Flights from Portland to Milwaukee (PWM-MKE)

Prices were available within the past 7 days and start at $136 for one-way flights and $271 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sun, Aug 31 - Sun, Sep 7
PWM
Portland
MKE
Milwaukee
$271 Roundtrip, found 13 hours ago
$271
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Sun, Aug 31 from Portland to Milwaukee, returning Sun, Sep 7, priced at $271 found 13 hours ago
American Airlines
Sun, May 25 - Wed, May 28
PWM
Portland
MKE
Milwaukee
$273 Roundtrip, found 9 hours ago
$273
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Sun, May 25 from Portland to Milwaukee, returning Wed, May 28, priced at $273 found 9 hours ago
American Airlines
Sun, Aug 31 - Sun, Sep 7
PWM
Portland
MKE
Milwaukee
$275 Roundtrip, found 13 hours ago
$275
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Sun, Aug 31 from Portland to Milwaukee, returning Sun, Sep 7, priced at $275 found 13 hours ago
Southwest Airlines
Wed, May 28 - Sat, May 31
PWM
Portland
MKE
Milwaukee
$284 Roundtrip, found 9 hours ago
$284
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Wed, May 28 from Portland to Milwaukee, returning Sat, May 31, priced at $284 found 9 hours ago
United
Sun, May 25 - Thu, May 29
PWM
Portland
MKE
Milwaukee
$284 Roundtrip, found 9 hours ago
$284
Roundtrip
found 9 hours ago
Select United flight, departing Sun, May 25 from Portland to Milwaukee, returning Thu, May 29, priced at $284 found 9 hours ago
American Airlines
Sun, May 25 - Thu, May 29
PWM
Portland
MKE
Milwaukee
$286 Roundtrip, found 9 hours ago
$286
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Sun, May 25 from Portland to Milwaukee, returning Thu, May 29, priced at $286 found 9 hours ago
Delta
Sun, Aug 31 - Sat, Sep 6
PWM
Portland
MKE
Milwaukee
$288 Roundtrip, found 18 hours ago
$288
Roundtrip
found 18 hours ago
Select Delta flight, departing Sun, Aug 31 from Portland to Milwaukee, returning Sat, Sep 6, priced at $288 found 18 hours ago
United
Tue, Jun 17 - Wed, Jul 2
PWM
Portland
MKE
Milwaukee
$289 Roundtrip, found 3 days ago
$289
Roundtrip
found 3 days ago
Select United flight, departing Tue, Jun 17 from Portland to Milwaukee, returning Wed, Jul 2, priced at $289 found 3 days ago
Delta
Fri, Jul 4 - Mon, Jul 7
PWM
Portland
MKE
Milwaukee
$291 Roundtrip, found 9 hours ago
$291
Roundtrip
found 9 hours ago
Select Delta flight, departing Fri, Jul 4 from Portland to Milwaukee, returning Mon, Jul 7, priced at $291 found 9 hours ago
Sun Country Airlines
Sun, Jun 8 - Mon, Jun 16
PWM
Portland
MKE
Milwaukee
$313 Roundtrip, found 11 hours ago
$313
Roundtrip
found 11 hours ago
Select Sun Country Airlines flight, departing Sun, Jun 8 from Portland to Milwaukee, returning Mon, Jun 16, priced at $313 found 11 hours ago
Flights from Portland (PWM) to Milwaukee (MKE)
Origin airport
Portland Intl. Jetport
Destination airport
General Mitchell Intl.
Airlines serving
American Airlines, Delta, JetBlue Airways, Southwest Airlines, United
Roundtrip price
$270
Distance
884 mi

Portland to Milwaukee Flights

The cheapest times to fly from Portland to Milwaukee

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Portland to Milwaukee are during the month of August. You can find some of the cheapest flights from Portland to Milwaukee with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Portland to Milwaukee

Sunday is one of the best days to book for cheap flights from Portland to Milwaukee: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Portland to Milwaukee

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Portland to Milwaukee in 2025. You can also book with separate airlines for your outbound and return journeys, from $136 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Portland to Milwaukee flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Portland to Milwaukee airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently asked questions

How much does a flight from Portland Intl. Jetport Airport (PWM) to General Mitchell Intl. Airport (MKE) cost?
Discover the latest flight deals from PWM to MKE by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from PWM to MKE?
The cheapest flights from PWM to MKE are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from PWM to MKE?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from PWM to MKE. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from Portland Intl. Jetport Airport (PWM) to General Mitchell Intl. Airport (MKE)?
There are no daily nonstop flights departing from Portland Intl. Jetport Airport (PWM) to General Mitchell Intl. Airport (MKE). But you can choose flights with layovers. Filter your search results on Expedia to include one or more stops, and you’ll be soaring above the clouds in no time.
What day of the week has the most flights from PWM to MKE?
Generally you’ll have the most choice when it comes to flights on a Friday. Tuesdays tend to be the quietest.* However, this can vary based on the season, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What airline has the least delays from PWM to MKE?
Consider booking with United Airlines if you’d like to go straight from Portland Intl. Jetport Airport (PWM) to General Mitchell Intl. Airport (MKE) without any holdups. This airline has the best track record for punctuality, with an on-time performance of 83%. Want real-time updates? You can check your flight status using the Expedia App.
What is the best time to fly from Portland Intl. Jetport Airport (PWM) to General Mitchell Intl. Airport (MKE)?
To avoid potential delays on the Portland Intl. Jetport Airport (PWM) to General Mitchell Intl. Airport (MKE) route, travel before 3 PM. Departures after this hour have a 22% higher chance of cancellation.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
Is it cheaper to buy a plane ticket from Portland Intl. Jetport Airport (PWM) to General Mitchell Intl. Airport (MKE) last-minute?
Booking your ticket from PWM to MKE just before your trip is usually more expensive. However, if there’s some wiggle room with your itinerary, you could score a cheap last-minute fare.
Is it cheaper to book a PWM to MKE flight and hotel package?
Compared with arranging flights and hotels separately, booking a PWM to MKE flight and hotel package with Expedia could result in significant savings. Better still, having it all in one place will take the stress out of planning your trip. Simply secure your flights and select from our wide range of hotels, then personalize your trip with other add-ons like tours and car rentals.
Can I cancel or change the date of my flight from Portland Intl. Jetport Airport (PWM) to General Mitchell Intl. Airport (MKE)?
Usually, it’s possible to cancel or reschedule your PWM to MKE flight. However, if it’s been more than 24 hours since booking, additional charges may apply. Check your airline’s policies in your itinerary to see what changes are possible and if any costs are involved. You’ll also find further details on our Customer Service portal.

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*Available to One Key members.