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Cheap flights from Chicago Midway Airport to Milwaukee from $110

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 11/11. 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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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
6:10 pm - 11:25 pmMDW-MKE
5h 15m1 stop
Southwest Logo
4:05 pm - 10:35 pmMKE-MDW
6h 30m1 stop
$248Southwest
Find Deal
lun., nov. 10 - lun., nov. 17
Southwest Logo
5:35 am - 12:00 pmMDW-MKE
6h 25m1 stop
Southwest Logo
4:05 pm - 10:35 pmMKE-MDW
6h 30m1 stop
$267Southwest
Find Deal
mié., nov. 12 - mié., nov. 12
Southwest Logo
9:30 am - 5:25 pmMDW-MKE
7h 55m2 stops
Southwest Logo
4:05 pm - 10:35 pmMKE-MDW
6h 30m1 stop
$293Southwest
Find Deal
lun., nov. 10 - lun., nov. 17
Southwest Logo
6:20 am - 11:15 amMDW-MKE
4h 55m1 stop
Southwest Logo
5:50 am - 9:55 amMKE-MDW
4h 05m1 stop
$317Southwest
Find Deal
jue., nov. 6 - dom., nov. 9
Southwest Logo
5:35 am - 12:15 pmMDW-MKE
6h 40m1 stop
Southwest Logo
5:00 am - 10:10 amMKE-MDW
5h 10m1 stop
$327Southwest
Find Deal
jue., nov. 27 - lun., dic. 1
Southwest Logo
9:30 am - 5:25 pmMDW-MKE
7h 55m2 stops
Southwest Logo
5:50 am - 9:55 amMKE-MDW
4h 05m1 stop
$363Southwest
Find Deal
jue., nov. 6 - dom., nov. 9
Frontier Logo
12:11 pm - 7:18 pmMDW-MKE
7h 07m1 stop
Frontier Logo
8:04 pm - 11:38 amMKE-MDW
15h 34m2 stops
$371Frontier
Find Deal
vie., oct. 24 - lun., oct. 27
Southwest Logo
6:55 pm - 10:35 pmMDW-MKE
3h 40m1 stop
Southwest Logo
4:05 pm - 10:05 pmMKE-MDW
6h 00m1 stop
$379Southwest
Find Deal
lun., oct. 20 - mar., oct. 21
Multiple Airlines Logo
12:11 pm - 7:18 pmMDW-MKE
7h 07m1 stop
Multiple Airlines Logo
7:38 pm - 10:26 amMKE-MDW
14h 48m2 stops
$381Multiple Airlines
Find Deal
lun., oct. 27 - vie., oct. 31
Frontier Logo
12:11 pm - 7:18 pmMDW-MKE
7h 07m1 stop
Frontier Logo
8:04 pm - 11:38 amMKE-MDW
15h 34m2 stops
$418Frontier
Find Deal
vie., oct. 24 - lun., oct. 27

Southwest flights from Chicago Midway Airport to Milwaukee

Our best Southwest deals on Chicago Midway Airport to Milwaukee flight tickets
Southwest
Nov 10
MDW6:10 pmChicago Midway
5h 15m
1 stop
MKE11:25 pmMilwaukee-Mitchell
Nov 17
MKE4:05 pmMilwaukee-Mitchell
6h 30m
1 stop
MDW10:35 pmChicago Midway
$248
Find similar
Southwest
Nov 12
MDW5:35 amChicago Midway
6h 25m
1 stop
MKE12:00 pmMilwaukee-Mitchell
Nov 12
MKE4:05 pmMilwaukee-Mitchell
6h 30m
1 stop
MDW10:35 pmChicago Midway
$267
Find similar
Southwest
Nov 10
MDW9:30 amChicago Midway
7h 55m
2 stops
MKE5:25 pmMilwaukee-Mitchell
Nov 17
MKE4:05 pmMilwaukee-Mitchell
6h 30m
1 stop
MDW10:35 pmChicago Midway
$293
Find similar

Frontier flights from Chicago Midway Airport to Milwaukee

Our best Frontier deals on Chicago Midway Airport to Milwaukee flight tickets
Frontier
Oct 24
MDW12:11 pmChicago Midway
7h 07m
1 stop
MKE7:18 pmMilwaukee-Mitchell
Oct 27
MKE8:04 pmMilwaukee-Mitchell
15h 34m
2 stops
MDW11:38 amChicago Midway
$371
Find similar
Frontier
Oct 24
MDW12:11 pmChicago Midway
7h 07m
1 stop
MKE7:18 pmMilwaukee-Mitchell
Oct 27
MKE8:04 pmMilwaukee-Mitchell
15h 34m
2 stops
MDW11:38 amChicago Midway
$418
Find similar

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 octubre 14, 2025.
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

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

lun. 11/10

6:10 pm-11:25 pm

1 stop5h 15m

Milwaukee-Mitchell

lun. 11/17

4:05 pm-10:35 pm

1 stop6h 30m

$248

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

mié. 11/12

5:35 am-12:00 pm

1 stop6h 25m

Milwaukee-Mitchell

mié. 11/12

4:05 pm-10:35 pm

1 stop6h 30m

$267

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

lun. 11/10

9:30 am-5:25 pm

2 stops7h 55m

Milwaukee-Mitchell

lun. 11/17

4:05 pm-10:35 pm

1 stop6h 30m

$293

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

jue. 11/6

6:20 am-11:15 am

1 stop4h 55m

Milwaukee-Mitchell

dom. 11/9

5:50 am-9:55 am

1 stop4h 05m

$317

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

jue. 11/27

5:35 am-12:15 pm

1 stop6h 40m

Milwaukee-Mitchell

lun. 12/1

5:00 am-10:10 am

1 stop5h 10m

$327

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

jue. 11/6

9:30 am-5:25 pm

2 stops7h 55m

Milwaukee-Mitchell

dom. 11/9

5:50 am-9:55 am

1 stop4h 05m

$363

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

vie. 10/24

12:11 pm-7:18 pm

1 stop7h 07m

Milwaukee-Mitchell

lun. 10/27

8:04 pm-11:38 am

2 stops15h 34m

$371

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

lun. 10/20

6:55 pm-10:35 pm

1 stop3h 40m

Milwaukee-Mitchell

mar. 10/21

4:05 pm-10:05 pm

1 stop6h 00m

$379

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

lun. 10/27

12:11 pm-7:18 pm

1 stop7h 07m

Milwaukee-Mitchell

vie. 10/31

7:38 pm-10:26 am

2 stops14h 48m

$381

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

vie. 10/24

12:11 pm-7:18 pm

1 stop7h 07m

Milwaukee-Mitchell

lun. 10/27

8:04 pm-11:38 am

2 stops15h 34m

$418

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, Friday is the cheapest day to fly to Milwaukee from Chicago Midway Airport. The lowest ticket price found for a Friday departure recently was $218. 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 $371. 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 $289 per ticket.

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

Mon, Sat and Sun

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 on Monday, Saturday and Sunday. There are no airlines offering direct flights.
There is 1 airport near Milwaukee: Milwaukee-Mitchell (MKE)
Search flight deals

  • 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 3h 40m.

  • 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.

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
Kohler
Pewaukee
West Bend
Port Washington
Grafton
New Berlin

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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