$100 Cheap Flights from Chicago (MDW) to Milwaukee (MKE)

View $100 flight on Mon, Dec 15, 2025Opens in a new window

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

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Cheap Flights from Chicago to Milwaukee (MDW-MKE)

Prices were available within the past 7 days and start at $100 for one-way flights and $219 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Thu, Dec 4 - Sun, Dec 14
MDW
Chicago
MKE
Milwaukee
$219 Roundtrip, found 2 days ago
$219
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Dec 4 from Chicago to Milwaukee, returning Sun, Dec 14, priced at $219 found 2 days ago
Southwest Airlines
Thu, Dec 4 - Sun, Dec 14
MDW
Chicago
MKE
Milwaukee
$228 Roundtrip, found 2 days ago
$228
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Dec 4 from Chicago to Milwaukee, returning Sun, Dec 14, priced at $228 found 2 days ago
Southwest Airlines
Thu, Dec 4 - Sun, Dec 14
MDW
Chicago
MKE
Milwaukee
$237 Roundtrip, found 2 days ago
$237
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Dec 4 from Chicago to Milwaukee, returning Sun, Dec 14, priced at $237 found 2 days ago
Southwest Airlines
Thu, Dec 4 - Sun, Dec 7
MDW
Chicago
MKE
Milwaukee
$238 Roundtrip, found 3 days ago
$238
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Dec 4 from Chicago to Milwaukee, returning Sun, Dec 7, priced at $238 found 3 days ago
Southwest Airlines
Sat, Apr 18 - Sat, Apr 25
MDW
Chicago
MKE
Milwaukee
$238 Roundtrip, found 5 days ago
$238
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Apr 18 from Chicago to Milwaukee, returning Sat, Apr 25, priced at $238 found 5 days ago
Southwest Airlines
Thu, Dec 4 - Sun, Dec 7
MDW
Chicago
MKE
Milwaukee
$247 Roundtrip, found 3 days ago
$247
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Dec 4 from Chicago to Milwaukee, returning Sun, Dec 7, priced at $247 found 3 days ago
Southwest Airlines
Fri, Apr 17 - Mon, Apr 20
MDW
Chicago
MKE
Milwaukee
$248 Roundtrip, found 5 days ago
$248
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Fri, Apr 17 from Chicago to Milwaukee, returning Mon, Apr 20, priced at $248 found 5 days ago
Southwest Airlines
Sat, Mar 21 - Mon, Mar 23
MDW
Chicago
MKE
Milwaukee
$250 Roundtrip, found 12 hours ago
$250
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Sat, Mar 21 from Chicago to Milwaukee, returning Mon, Mar 23, priced at $250 found 12 hours ago
Southwest Airlines
Thu, Dec 4 - Sun, Dec 7
MDW
Chicago
MKE
Milwaukee
$252 Roundtrip, found 3 days ago
$252
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Dec 4 from Chicago to Milwaukee, returning Sun, Dec 7, priced at $252 found 3 days ago
Delta
Wed, Dec 3 - Mon, Dec 22
MDW
Chicago
MKE
Milwaukee
$385 Roundtrip, found 3 days ago
$385
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Dec 3 from Chicago to Milwaukee, returning Mon, Dec 22, priced at $385 found 3 days ago

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to General Mitchell Intl. Airport (MKE) cost?
Secure a cheap one-way flight from $100 or cheap return flight from $219 from Midway Intl. Airport (MDW) to General Mitchell Intl. Airport (MKE) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to General Mitchell Intl. Airport (MKE)?
Planning your trip for December can help you save, as it's the cheapest month for flights between MDW and MKE. You'll usually find the lowest fares during off-peak months.
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 Midway Intl. Airport (MDW) to General Mitchell Intl. Airport (MKE)?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from MDW to MKE. Then, sort your results by "Price (lowest to highest)" to score the best deal available.
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.

Travel information

Origin airport
Midway Intl.
Destination airport
General Mitchell Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$218
Distance
80 mi

Book with confidence

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 December. 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 $100 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.

 

Chicago to Milwaukee Flights

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*Available to One Key members.