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Cheap flights from Chicago Midway Airport to Milwaukee from $99

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Milwaukee departing on 6/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago Midway Airport to Milwaukee

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
9:00 pm - 9:45 pm
MDW
-
MKE
0h 45mnonstop
Southwest Logo
6:00 am - 6:50 am
MKE
-
MDW
0h 50mnonstop
$197Southwest
Tue, Jun 2 - Tue, Jun 9
Southwest Logo
9:55 pm - 10:45 pm
MDW
-
MKE
0h 50mnonstop
Southwest Logo
6:00 am - 6:50 am
MKE
-
MDW
0h 50mnonstop
$199Southwest
Mon, Jun 8 - Tue, Jun 16
Southwest Logo
9:30 pm - 10:15 pm
MDW
-
MKE
0h 45mnonstop
Southwest Logo
4:50 pm - 5:40 pm
MKE
-
MDW
0h 50mnonstop
$201Southwest
Thu, May 28 - Mon, Jun 1
Southwest Logo
10:10 am - 10:55 am
MDW
-
MKE
0h 45mnonstop
Southwest Logo
12:25 pm - 5:10 pm
MKE
-
MDW
4h 45m
1 stop
$207Southwest
Tue, Jun 2 - Tue, Jun 9
Southwest Logo
10:10 am - 10:55 am
MDW
-
MKE
0h 45mnonstop
Southwest Logo
6:00 am - 6:50 am
MKE
-
MDW
0h 50mnonstop
$208Southwest
Wed, Jun 3 - Sun, Jun 7
Southwest Logo
9:55 pm - 10:45 pm
MDW
-
MKE
0h 50mnonstop
Southwest Logo
3:40 pm - 8:55 pm
MKE
-
MDW
5h 15m
1 stop
$209Southwest
Mon, Jun 8 - Tue, Jun 16
Southwest Logo
9:55 pm - 10:45 pm
MDW
-
MKE
0h 50mnonstop
Southwest Logo
5:40 am - 6:30 am
MKE
-
MDW
0h 50mnonstop
$210Southwest
Thu, Jun 4 - Thu, Jun 11
Southwest Logo
9:30 pm - 10:15 pm
MDW
-
MKE
0h 45mnonstop
Southwest Logo
2:30 pm - 8:30 pm
MKE
-
MDW
6h 00m
1 stop
$211Southwest
Thu, May 28 - Mon, Jun 1
Southwest Logo
4:50 pm - 10:35 pm
MDW
-
MKE
5h 45m
1 stop
Southwest Logo
5:05 pm - 10:35 pm
MKE
-
MDW
5h 30m
1 stop
$217Southwest
Tue, Jun 2 - Tue, Jun 9
Southwest Logo
4:40 pm - 10:15 pm
MDW
-
MKE
5h 35m
1 stop
Southwest Logo
5:05 pm - 6:00 pm
MKE
-
MDW
0h 55mnonstop
$218Southwest
Wed, Jun 3 - Sun, Jun 7

Southwest flights from Chicago Midway Airport to Milwaukee

Our best Southwest deals on Chicago Midway Airport to Milwaukee flight tickets
Southwest
Jun 2
MDW9:00 pmChicago Midway
0h 45m
MKE9:45 pmMilwaukee-Mitchell
Jun 9
MKE6:00 amMilwaukee-Mitchell
0h 50m
MDW6:50 amChicago Midway
$197
Southwest
Jun 8
MDW9:55 pmChicago Midway
0h 50m
MKE10:45 pmMilwaukee-Mitchell
Jun 16
MKE6:00 amMilwaukee-Mitchell
0h 50m
MDW6:50 amChicago Midway
$199
Southwest
May 28
MDW9:30 pmChicago Midway
0h 45m
MKE10:15 pmMilwaukee-Mitchell
Jun 1
MKE4:50 pmMilwaukee-Mitchell
0h 50m
MDW5:40 pmChicago Midway
$201

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated May 10, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Milwaukee that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Tue 6/2

9:00 pm-9:45 pm

Nonstop0h 45m

Milwaukee-Mitchell

Tue 6/9

6:00 am-6:50 am

Nonstop0h 50m

$197

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Mon 6/8

9:55 pm-10:45 pm

Nonstop0h 50m

Milwaukee-Mitchell

Tue 6/16

6:00 am-6:50 am

Nonstop0h 50m

$199

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Thu 5/28

9:30 pm-10:15 pm

Nonstop0h 45m

Milwaukee-Mitchell

Mon 6/1

4:50 pm-5:40 pm

Nonstop0h 50m

$201

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Tue 6/2

10:10 am-10:55 am

Nonstop0h 45m

Milwaukee-Mitchell

Tue 6/9

12:25 pm-5:10 pm

1 stop4h 45m

$207

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Wed 6/3

10:10 am-10:55 am

Nonstop0h 45m

Milwaukee-Mitchell

Sun 6/7

6:00 am-6:50 am

Nonstop0h 50m

$208

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Mon 6/8

9:55 pm-10:45 pm

Nonstop0h 50m

Milwaukee-Mitchell

Tue 6/16

3:40 pm-8:55 pm

1 stop5h 15m

$209

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Thu 6/4

9:55 pm-10:45 pm

Nonstop0h 50m

Milwaukee-Mitchell

Thu 6/11

5:40 am-6:30 am

Nonstop0h 50m

$210

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Thu 5/28

9:30 pm-10:15 pm

Nonstop0h 45m

Milwaukee-Mitchell

Mon 6/1

2:30 pm-8:30 pm

1 stop6h 00m

$211

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Tue 6/2

4:50 pm-10:35 pm

1 stop5h 45m

Milwaukee-Mitchell

Tue 6/9

5:05 pm-10:35 pm

1 stop5h 30m

$217

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Wed 6/3

4:40 pm-10:15 pm

1 stop5h 35m

Milwaukee-Mitchell

Sun 6/7

5:05 pm-6:00 pm

Nonstop0h 55m

$218

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Milwaukee from

How to get the cheapest flight ticket from Chicago Midway Airport to Milwaukee

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Milwaukee?

According to our data, Monday is the cheapest day to fly to Milwaukee from Chicago Midway Airport. The lowest ticket price found for a Monday departure recently was $201. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. Flights from Chicago Midway Airport to Milwaukee on a Thursday will generally be more expensive and average around $327. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Milwaukee?

In the evening is the cheapest time of day to fly from Chicago Midway Airport to Milwaukee when you can find flight prices for as low as $199. Flying to Milwaukee in the evening is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Milwaukee, so prices are often more expensive at around $320 per ticket.

What is the cheapest Chicago Midway to Milwaukee-Mitchell flight route?

Fly from Chicago Midway to Milwaukee-Mitchell for the best Chicago Midway - Milwaukee-Mitchell flight prices

Can stopping save me money on Chicago Midway Airport to Milwaukee flights?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Milwaukee.

When to book flights from Chicago Midway Airport to Milwaukee

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Milwaukee according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Milwaukee (MDW to MKE) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Milwaukee

Fastest flight time

0h 45m

Direct flights

Every day

Airports in Milwaukee

1 airport
The fastest flight from Chicago Midway Airport to Milwaukee takes 0h 45m
Direct flights go from Chicago Midway Airport to Milwaukee every day.
There is 1 airport in Milwaukee. From Chicago Midway Airport there are direct flights to Milwaukee-Mitchell (MKE).
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Milwaukee

  • How far is Chicago Midway to Milwaukee-Mitchell by plane?

    The straight-line distance from Chicago Midway to Milwaukee-Mitchell is 86.8 mi. By plane, this route typically takes 0h 45m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Milwaukee-Mitchell Airport?

    Prices for flights from Chicago Midway Airport to Milwaukee-Mitchell Airport refresh daily.

  • How old do you have to be to fly from Chicago Midway Airport to Milwaukee-Mitchell Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Milwaukee-Mitchell Airport.

  • What documentation or ID do you need to fly to Milwaukee-Mitchell Airport?

    The necessary travel and health documents for your Milwaukee-Mitchell Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to Milwaukee?

Traveling to a place near Milwaukee?

Book flights to Milwaukee if you plan to visit one of these locations
Sheboygan
Waukesha
Wauwatosa
Oak Creek
Mequon
Glendale
Pewaukee
West Bend
Port Washington
Kohler
New Berlin
Grafton

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Milwaukee?

It is quick and easy to find Chicago to Milwaukee flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Milwaukee that suits you.

Can I find flights from Chicago to Milwaukee with flexible booking policies on momondo?

Flights from Chicago to Milwaukee with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Milwaukee?

momondo provides multiple filters to help you find the best flight to Milwaukee from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Milwaukee right now. Can momondo alert me if prices change?

Price alerts on flights to Milwaukee from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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