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$86+ 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 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MKE
Aug 27 — Sep 31
Thu 8/27
Thu 9/3
1 adult, Economy
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Cheap 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 July 28, 2026.

This Southwest deal was found by Cheapflights users on 7/23. 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.
Thu 8/208:40 pm
MDW
-
MKE
Nonstop0h 45m
Southwest
Thu 8/275:45 am
MKE
-
MDW
Nonstop0h 45m
Southwest
Deal found 7/23$171
This Southwest deal was found by Cheapflights users on 7/24. 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.
Tue 9/88:35 pm
MDW
-
MKE
Nonstop0h 45m
Southwest
Tue 9/153:10 pm
MKE
-
MDW
Nonstop0h 50m
Southwest
Deal found 7/24$179
This Southwest deal was found by Cheapflights users on 7/23. 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.
Tue 9/84:40 pm
MDW
-
MKE
1 stop3h 20m
Southwest
Thu 9/104:50 pm
MKE
-
MDW
1 stop5h 10m
Southwest
Deal found 7/23$191
This Southwest deal was found by Cheapflights users on 7/26. 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.
Wed 9/91:00 pm
MDW
-
MKE
2 stops7h 35m
Southwest
Wed 9/163:40 pm
MKE
-
MDW
Nonstop0h 50m
Southwest
Deal found 7/26$194
This Southwest deal was found by Cheapflights users on 7/27. 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.
Fri 10/29:40 pm
MDW
-
MKE
Nonstop0h 50m
Southwest
Mon 10/55:00 pm
MKE
-
MDW
Nonstop0h 50m
Southwest
Deal found 7/27$197
This Southwest deal was found by Cheapflights users on 7/25. 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.
Sat 8/157:45 am
MDW
-
MKE
1 stop4h 50m
Southwest
Sun 8/165:45 am
MKE
-
MDW
Nonstop0h 45m
Southwest
Deal found 7/25$214

Find 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 July 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$171
(Southwest)

One-way from

$86
(Southwest)
Provider with most accurate pricing for Chicago Midway-Milwaukee-Mitchell flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Milwaukee-Mitchell flights.
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From Chicago Midway to Milwaukee-Mitchell
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One-way flight from Chicago Midway to Milwaukee-Mitchell
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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 July 28, 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

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Thu 8/20

8:40 pm-9:25 pm

Nonstop0h 45m

Milwaukee-Mitchell

Mon 8/24

4:20 pm-5:10 pm

Nonstop0h 50m

$179
Quickest round-trip

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Mon 9/7

8:40 pm-9:25 pm

Nonstop0h 45m

Milwaukee-Mitchell

Mon 9/14

5:45 am-6:30 am

Nonstop0h 45m

$179

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Mon 8/17

8:40 pm-9:25 pm

Nonstop0h 45m

Milwaukee-Mitchell

Thu 8/20

4:20 pm-5:10 pm

Nonstop0h 50m

$179

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Thu 8/20

8:40 pm-9:25 pm

Nonstop0h 45m

Milwaukee-Mitchell

Thu 8/27

4:00 pm-9:30 pm

1 stop5h 30m

$181

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Tue 9/8

10:15 am-11:05 am

Nonstop0h 50m

Milwaukee-Mitchell

Tue 9/15

11:45 am-3:25 pm

1 stop3h 40m

$189

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Mon 8/17

8:40 pm-9:25 pm

Nonstop0h 45m

Milwaukee-Mitchell

Wed 8/26

11:45 am-3:25 pm

1 stop3h 40m

$189

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Wed 9/9

4:40 pm-8:00 pm

1 stop3h 20m

Milwaukee-Mitchell

Wed 9/16

6:40 am-7:30 am

Nonstop0h 50m

$189

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Sat 8/15

7:45 am-12:35 pm

1 stop4h 50m

Milwaukee-Mitchell

Mon 8/17

4:50 pm-9:55 pm

1 stop5h 05m

$199
Cheapest one-way
Quickest one-way

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Sat 10/24

7:15 pm-8:00 pm

Nonstop0h 45m

$90

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Mon 10/26

5:50 pm-11:05 pm

1 stop5h 15m

$100

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/25

Showing 1-10 of 17 resultsSorted by cheapest first
1
2
  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Milwaukee flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Milwaukee flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Milwaukee flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Milwaukee flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Milwaukee flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Milwaukee

What is the cheapest time of day to fly from MDW to MKE?

Find hourly flight availability from Midway to Milwaukee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 28, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Milwaukee as you normally would.

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 1 inbound flight 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 45m. Southwest provides one of the quickest options available for as low as $179. There are 80 mi between Chicago Midway Airport and Milwaukee. All flights are typically nonstop.

  • 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.

See more FAQs

Traveling to a place near Milwaukee?

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

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