$93 Cheap Flights from Milwaukee (MKE) to Chicago (MDW)

View $93 flight on Mon, Dec 8, 2025Opens in a new window

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

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Cheap Flights from Milwaukee to Chicago (MKE-MDW)

Prices were available within the past 7 days and start at $93 for one-way flights and $199 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Dec 10 - Mon, Dec 15
MKE
Milwaukee
MDW
Chicago
$199 Roundtrip, found 4 days ago
$199
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Dec 10 from Milwaukee to Chicago, returning Mon, Dec 15, priced at $199 found 4 days ago
Southwest Airlines
Wed, Dec 10 - Mon, Dec 15
MKE
Milwaukee
MDW
Chicago
$214 Roundtrip, found 4 days ago
$214
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Dec 10 from Milwaukee to Chicago, returning Mon, Dec 15, priced at $214 found 4 days ago
Southwest Airlines
Mon, Jan 19 - Tue, Jan 20
MKE
Milwaukee
MDW
Chicago
$218 Roundtrip, found 1 day ago
$218
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Mon, Jan 19 from Milwaukee to Chicago, returning Tue, Jan 20, priced at $218 found 1 day ago
Southwest Airlines
Sat, Feb 7 - Tue, Feb 17
MKE
Milwaukee
MDW
Chicago
$219 Roundtrip, found 9 hours ago
$219
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Sat, Feb 7 from Milwaukee to Chicago, returning Tue, Feb 17, priced at $219 found 9 hours ago
Southwest Airlines
Tue, Feb 24 - Wed, Feb 25
MKE
Milwaukee
MDW
Chicago
$223 Roundtrip, found 6 days ago
$223
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Feb 24 from Milwaukee to Chicago, returning Wed, Feb 25, priced at $223 found 6 days ago
Southwest Airlines
Thu, Jan 22 - Mon, Feb 2
MKE
Milwaukee
MDW
Chicago
$224 Roundtrip, found 1 day ago
$224
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Jan 22 from Milwaukee to Chicago, returning Mon, Feb 2, priced at $224 found 1 day ago
Southwest Airlines
Sat, Feb 7 - Tue, Feb 17
MKE
Milwaukee
MDW
Chicago
$228 Roundtrip, found 9 hours ago
$228
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Sat, Feb 7 from Milwaukee to Chicago, returning Tue, Feb 17, priced at $228 found 9 hours ago
Southwest Airlines
Mon, Jan 19 - Tue, Jan 20
MKE
Milwaukee
MDW
Chicago
$229 Roundtrip, found 1 day ago
$229
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Mon, Jan 19 from Milwaukee to Chicago, returning Tue, Jan 20, priced at $229 found 1 day ago
Southwest Airlines
Thu, Jan 22 - Mon, Feb 2
MKE
Milwaukee
MDW
Chicago
$233 Roundtrip, found 1 day ago
$233
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Jan 22 from Milwaukee to Chicago, returning Mon, Feb 2, priced at $233 found 1 day ago
Delta
Sun, Jan 18 - Wed, Jan 28
MKE
Milwaukee
MDW
Chicago
$405 Roundtrip, found 1 day ago
$405
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Jan 18 from Milwaukee to Chicago, returning Wed, Jan 28, priced at $405 found 1 day ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $194
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $194
Flights from Milwaukee (MKE) to Chicago (MDW)
Origin airport
General Mitchell Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$198
Distance
80 mi

Milwaukee to Chicago Flights

The cheapest times to fly from Milwaukee to Chicago

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

 

The best time to book a flight from Milwaukee to Chicago

Sunday is one of the best days to book for cheap flights from Milwaukee to Chicago: 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 Milwaukee to Chicago

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 Milwaukee to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $93 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 Milwaukee to Chicago 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 Milwaukee to Chicago 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 General Mitchell Intl. Airport (MKE) to Midway Intl. Airport (MDW) cost?
Grab a cheap one-way flight from $93 or cheap return flight from $199 from General Mitchell Intl. Airport (MKE) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from General Mitchell Intl. Airport (MKE) to Midway Intl. Airport (MDW)?
December is the cheapest month to fly from MKE to MDW. Traveling during quieter months is often the key to better flight prices.
What is the cheapest airline that flies from General Mitchell Intl. Airport (MKE) to Midway Intl. Airport (MDW)?
To find the cheapest airline flying from MKE to MDW, use Expedia's filter tool. Tailor your search based on what's important to you, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
How many flights per day from General Mitchell Intl. Airport (MKE) to Midway Intl. Airport (MDW)?
You'll need to hop on a flight with a layover if you're traveling from General Mitchell Intl. Airport (MKE) to Midway Intl. Airport (MDW). Direct flights don't operate daily on this route. However, simply filter your search to include one or two stops to discover the best option for your trip.
What day of the week has the most flights from MKE to MDW?
Generally you'll find the most flight options available on a Friday. Tuesdays tend to be the quietest.* But 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 is the best time to fly from General Mitchell Intl. Airport (MKE) to Midway Intl. Airport (MDW)?
To reach Midway Intl. Airport (MDW) on time, choose a flight that takes off from General Mitchell Intl. Airport (MKE) 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.
What airports do you fly into for Chicago from General Mitchell Intl. Airport (MKE)?
Browse your flight options from General Mitchell Intl. Airport (MKE) to O'Hare Intl. Airport (ORD). This is the only Chicago airport you can arrive at if you're taking a direct flight.
Is it cheaper to buy a plane ticket from General Mitchell Intl. Airport (MKE) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from MKE to MDW are generally more expensive. To secure the lowest rates, start searching for flights ahead of time. That being said, if you're flexible with your travel dates, you may find a cheap ticket right before you leave.
Is it cheaper to book a MKE to MDW flight and hotel package?
Compared with arranging flights and hotels separately, booking a MKE to MDW flight and hotel package with Expedia could lead to significant savings. Better still, having it all in one place takes the hassle out of planning your trip. Simply pick your flights and select from our wide range of stays, then tailor your trip with other add-ons like activities and car rentals.
Can I cancel or change the date of my flight from General Mitchell Intl. Airport (MKE) to Midway Intl. Airport (MDW)?
In most instances, you're able to cancel or reschedule your MKE to MDW flight. However, there may be additional fees, especially if you booked more than 24 hours ago. Double-check your itinerary for the airline's fees and policies on flight changes, or if you need more details, head to our Customer Service portal.

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*Available to One Key members.