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$68+ Cheap flights from Midway (MDW) to Milwaukee (MKE)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MKE
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
1 adult, Economy
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Cheap flight deals from Midway to Milwaukee

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Milwaukee (MKE). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated septiembre 11, 2025.

Round-trip from

$143
(Southwest)

One-way from

$68
(Southwest)

Popular in

December

Cheapest in

September

Average price

$183
From Chicago Midway to Milwaukee-Mitchell
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One-way flight from Chicago Midway to Milwaukee-Mitchell
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Highest demand for flights based on searches. 25% potential increase in price ($95 potential increase over avg. RT price).
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Cheapest flight prices on average. 10% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Midway to Milwaukee

Cheapest flights from Midway to Milwaukee
Explore the most affordable flight options available from Midway to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/266:24 pmMDW - MKE
1 stop24h 54mMultiple Airlines
dom. 11/21:55 pmMKE - MDW
1 stop18h 37mMultiple Airlines
Deal found 9/11$278
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/97:00 pmMDW - MKE
1 stop4h 30mSouthwest
dom. 11/165:50 amMKE - MDW
1 stop4h 05mSouthwest
Deal found 9/11$301
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/2111:00 amMDW - MKE
1 stop6h 25mSouthwest
dom. 11/308:40 pmMKE - MDW
1 stop3h 15mSouthwest
Deal found 9/8$347
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/227:15 amMDW - MKE
2 stops12h 04mMultiple Airlines
jue. 9/2512:53 pmMKE - MDW
1 stop20h 00mMultiple Airlines
Deal found 9/9$509
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/105:40 pmMDW - MKE
1 stop4h 25mSouthwest
sáb. 9/133:55 pmMKE - MDW
1 stop3h 10mSouthwest
Deal found 9/8$527
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/126:05 pmMDW - MKE
1 stop3h 30mSouthwest
dom. 9/147:45 amMKE - MDW
1 stop7h 15mSouthwest
Deal found 9/10$532

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway 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, Cheapflights users made 2,558,603 searches. Data last updated septiembre 11, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Milwaukee that are best for you.

Fly from

Midway

Fly to

Milwaukee

Route

Depart

Return

Price

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

jue. 2/26

5:50 am-12:15 pm

1 stop6h 25m

Milwaukee-Mitchell

dom. 3/1

6:00 pm-9:10 pm

1 stop3h 10m

$220

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

dom. 10/26

6:24 pm-7:18 pm

1 stop24h 54m

Milwaukee-Mitchell

dom. 11/2

1:55 pm-8:32 am

1 stop18h 37m

$278

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

dom. 11/9

7:00 pm-11:30 pm

1 stop4h 30m

Milwaukee-Mitchell

dom. 11/16

5:50 am-9:55 am

1 stop4h 05m

$301

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

vie. 11/21

11:00 am-5:25 pm

1 stop6h 25m

Milwaukee-Mitchell

dom. 11/30

8:40 pm-11:55 pm

1 stop3h 15m

$347

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

lun. 9/22

7:15 am-7:19 pm

2 stops12h 04m

Milwaukee-Mitchell

jue. 9/25

12:53 pm-8:53 am

1 stop20h 00m

$509

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

mié. 2/25

2:00 pm-9:32 pm

1 stop7h 32m

Milwaukee-Mitchell

jue. 2/26

7:00 am-6:34 pm

1 stop11h 34m

$521

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

mié. 10/8

10:55 am-3:55 pm

1 stop5h 00m

$68

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

mar. 12/9

5:35 am-12:00 pm

1 stop6h 25m

$68

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

lun. 12/8

5:15 pm-9:30 pm

1 stop4h 15m

$84

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

lun. 11/10

7:00 pm-11:30 pm

1 stop4h 30m

$91

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/8

Showing 1-10 of 15 results
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Best time to book a flight from Midway to Milwaukee

Have a flexible travel schedule? Discover the best time to fly to Milwaukee from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

Find useful and relevant information for your journey from Midway to Milwaukee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Milwaukee from Chicago Midway?

    For a flight from Chicago Midway to Milwaukee, you will be flying into Milwaukee-Mitchell. Milwaukee-Mitchell (MKE) is just 6.4 mi from the center of the city. Milwaukee-Mitchell is the only Milwaukee airport and it handles 0 inbound flights from Chicago Midway per day. 0 airlines have flights to Milwaukee-Mitchell from Chicago Midway on a regular basis.

  • How long is the flight from Chicago Midway Airport to Milwaukee?

    A quick flight from Chicago Midway Airport to Milwaukee can take about 6h 25m. Southwest provides one of the quickest options available for as low as $220. There are 80 mi between Chicago Midway Airport and Milwaukee.

  • Can I find deals for flights from Midway to Milwaukee that include hotel bookings?

    Yes. In addition to deals on Midway to Milwaukee flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Milwaukee?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Milwaukee.

  • Can I find deals for business class flights from Midway to Milwaukee?

    Yes. Cheapflights offers flight deals from Midway to Milwaukee by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Milwaukee?

    Currently, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Milwaukee (average of $280). Flying from Chicago Midway Airport to Milwaukee in June is currently the most expensive (average of $376). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Milwaukee?

Book flights to Milwaukee if you plan to visit one of these locations
Sheboygan
Oak Creek
New Berlin
Wauwatosa

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