$138 Cheap Flights from Chicago (MDW) to Milwaukee (MKE)

View $138 flight on Mon, May 12, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to General Mitchell Intl. Airport (MKE)

Find available prices by choosing your travel dates.

Cheap Flights from Chicago to Milwaukee (MDW-MKE)

Prices were available within the past 7 days and start at $138 for one-way flights and $305 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Aug 5 - Mon, Aug 11
MDW
Chicago
MKE
Milwaukee
$305 Roundtrip, found 1 day ago
$305
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Aug 5 from Chicago to Milwaukee, returning Mon, Aug 11, priced at $305 found 1 day ago
Delta
Tue, Sep 9 - Mon, Sep 22
MDW
Chicago
MKE
Milwaukee
$325 Roundtrip, found 3 days ago
$325
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Sep 9 from Chicago to Milwaukee, returning Mon, Sep 22, priced at $325 found 3 days ago
Southwest Airlines
Mon, Sep 22 - Tue, Sep 30
MDW
Chicago
MKE
Milwaukee
$328 Roundtrip, found 3 days ago
$328
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Mon, Sep 22 from Chicago to Milwaukee, returning Tue, Sep 30, priced at $328 found 3 days ago
Delta
Tue, Sep 9 - Mon, Sep 29
MDW
Chicago
MKE
Milwaukee
$355 Roundtrip, found 3 days ago
$355
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Sep 9 from Chicago to Milwaukee, returning Mon, Sep 29, priced at $355 found 3 days ago
Delta
Tue, Aug 5 - Sun, Aug 10
MDW
Chicago
MKE
Milwaukee
$364 Roundtrip, found 1 day ago
$364
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Aug 5 from Chicago to Milwaukee, returning Sun, Aug 10, priced at $364 found 1 day ago
Delta
Sat, May 24 - Tue, Jun 10
MDW
Chicago
MKE
Milwaukee
$366 Roundtrip, found 5 days ago
$366
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, May 24 from Chicago to Milwaukee, returning Tue, Jun 10, priced at $366 found 5 days ago
Delta
Tue, Sep 9 - Wed, Sep 24
MDW
Chicago
MKE
Milwaukee
$375 Roundtrip, found 3 days ago
$375
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Sep 9 from Chicago to Milwaukee, returning Wed, Sep 24, priced at $375 found 3 days ago
Delta
Tue, Aug 19 - Sat, Sep 6
MDW
Chicago
MKE
Milwaukee
$377 Roundtrip, found 5 days ago
$377
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Aug 19 from Chicago to Milwaukee, returning Sat, Sep 6, priced at $377 found 5 days ago
Delta
Thu, Jul 31 - Tue, Aug 12
MDW
Chicago
MKE
Milwaukee
$379 Roundtrip, found 1 day ago
$379
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Jul 31 from Chicago to Milwaukee, returning Tue, Aug 12, priced at $379 found 1 day ago
Delta
Mon, Sep 22 - Tue, Sep 30
MDW
Chicago
MKE
Milwaukee
$385 Roundtrip, found 3 days ago
$385
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Sep 22 from Chicago to Milwaukee, returning Tue, Sep 30, priced at $385 found 3 days ago
Flights from Chicago (MDW) to Milwaukee (MKE)
Origin airport
Midway Intl.
Destination airport
General Mitchell Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$305
Distance
80 mi

Chicago to Milwaukee Flights

The cheapest times to fly from Chicago 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 Chicago to Milwaukee are during the month of August. You can find some of the cheapest flights from Chicago to Milwaukee with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Chicago to Milwaukee

Sunday is one of the best days to book for cheap flights from Chicago 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 Chicago 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 Chicago to Milwaukee in 2025. You can also book with separate airlines for your outbound and return journeys, from $138 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 Chicago 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 Chicago 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 Midway Intl. Airport (MDW) to General Mitchell Intl. Airport (MKE) cost?
Discover the latest flight deals from MDW 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 MDW to MKE?
The cheapest flights from MDW 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.
Which airlines fly direct from Midway Intl. Airport (MDW) to General Mitchell Intl. Airport (MKE)?
Although Chicago, IL (MDW-Midway Intl.) doesn’t have any direct flights to General Mitchell Intl. Airport (MKE), other airports have nonstop options. Traveling from O’Hare Intl. Airport (ORD) will get you to Milwaukee without any detours.
What is the cheapest airline that flies from MDW to MKE?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from MDW to MKE. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from Midway Intl. Airport (MDW) to General Mitchell Intl. Airport (MKE)?
Nonstop flights from Midway Intl. Airport (MDW) to General Mitchell Intl. Airport (MKE) aren’t available daily, so you’ll need to take a flight with a layover. Explore your options with Expedia’s filter tool. Enter your dates and click on either “1 Stop” or “2+ Stops.”
What day of the week has the most flights from MDW to MKE?
Friday is generally the busiest day for flights, while Tuesday is often the quietest.* Remember that flight schedules can vary based on various factors, including the time of year and carrier.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to General Mitchell Intl. Airport (MKE)?
To arrive at General Mitchell Intl. Airport (MKE) on time, select a flight that leaves from Midway Intl. Airport (MDW) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**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 Midway Intl. Airport (MDW) to General Mitchell Intl. Airport (MKE) last-minute?
Waiting until right before your break to book a ticket from MDW to MKE often results in higher prices. Although you may find some last-minute deals, there’s no guarantee. Keep your travel schedule open for the best chance of scoring a bargain.
Is it cheaper to book a MDW to MKE flight and hotel package?
Compared with arranging hotels and flights separately, booking a MDW to MKE flight and hotel package with Expedia could lead to significant savings. Better still, having everything in one convenient place will take the hassle out of planning your trip. Just pick your flights and choose from our wide range of hotels, then tailor your trip with other add-ons like activities, tours and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to General Mitchell Intl. Airport (MKE)?
If you booked your MDW to MKE flight within the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for more information.

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*Available to One Key members.