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$89+ 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 3/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MKE
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
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 January 27, 2026.

This Southwest deal was found by Cheapflights users on 1/25. 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 2/287:45 am
MDW
-
MKE
1 stop4h 00m
Southwest
Thu 3/54:55 pm
MKE
-
MDW
Nonstop0h 50m
Southwest
Deal found 1/25$224
This Southwest deal was found by Cheapflights users on 1/26. 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.
Fri 9/48:40 pm
MDW
-
MKE
Nonstop0h 45m
Southwest
Sat 9/125:45 am
MKE
-
MDW
Nonstop0h 45m
Southwest
Deal found 1/26$257
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/197:30 am
MDW
-
MKE
1 stop26h 13m
Frontier
Sun 2/226:37 pm
MKE
-
MDW
2 stops18h 31m
Frontier
Deal found 1/26$262
This Southwest deal was found by Cheapflights users on 1/26. 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.
Fri 4/249:30 pm
MDW
-
MKE
Nonstop0h 45m
Southwest
Fri 5/295:50 am
MKE
-
MDW
Nonstop0h 55m
Southwest
Deal found 1/26$267
This Southwest deal was found by Cheapflights users on 1/25. 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.
Thu 2/1911:00 am
MDW
-
MKE
1 stop5h 20m
Southwest
Sun 2/226:10 am
MKE
-
MDW
1 stop4h 25m
Southwest
Deal found 1/25$277
This Southwest deal was found by Cheapflights users on 1/26. 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.
Fri 2/64:55 pm
MDW
-
MKE
1 stop5h 45m
Southwest
Tue 2/103:50 pm
MKE
-
MDW
1 stop3h 15m
Southwest
Deal found 1/26$287
This Southwest deal was found by Cheapflights users on 1/25. 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.
Thu 1/296:10 am
MDW
-
MKE
1 stop5h 20m
Southwest
Sat 1/316:30 am
MKE
-
MDW
1 stop5h 05m
Southwest
Deal found 1/25$311
This Southwest deal was found by Cheapflights users on 1/25. 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.
Fri 2/137:55 am
MDW
-
MKE
1 stop4h 20m
Southwest
Sun 2/156:35 pm
MKE
-
MDW
1 stop3h 05m
Southwest
Deal found 1/25$327

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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$224
(Southwest)

One-way from

$89
(Southwest)
Provider with most accurate pricing for Chicago Midway-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Milwaukee-Mitchell flights.
Search Deals
From Chicago Midway to Milwaukee-Mitchell
Search Deals
One-way flight from Chicago Midway to Milwaukee-Mitchell
Search Deals

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 January 27, 2026.
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

Sat 2/28

7:45 am-11:45 am

1 stop4h 00m

Milwaukee-Mitchell

Thu 3/5

4:55 pm-5:45 pm

Nonstop0h 50m

$224

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Fri 4/24

9:30 pm-10:15 pm

Nonstop0h 45m

Milwaukee-Mitchell

Fri 5/29

5:50 am-6:45 am

Nonstop0h 55m

$267

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Thu 2/19

11:00 am-4:20 pm

1 stop5h 20m

Milwaukee-Mitchell

Sun 2/22

6:10 am-10:35 am

1 stop4h 25m

$277

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Fri 2/6

4:55 pm-10:40 pm

1 stop5h 45m

Milwaukee-Mitchell

Tue 2/10

3:50 pm-7:05 pm

1 stop3h 15m

$287

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Tue 2/10

2:35 pm-7:55 pm

1 stop5h 20m

Milwaukee-Mitchell

Sat 2/14

3:20 pm-7:55 pm

1 stop4h 35m

$287

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Thu 2/19

7:30 am-9:43 am

1 stop26h 13m

Milwaukee-Mitchell

Sun 2/22

6:37 pm-1:08 pm

2 stops18h 31m

$305

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Fri 2/13

7:55 am-12:15 pm

1 stop4h 20m

Milwaukee-Mitchell

Sun 2/15

6:35 pm-9:40 pm

1 stop3h 05m

$327

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Sat 5/9

10:30 am-11:15 am

Nonstop0h 45m

$90

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Sat 5/16

6:10 pm-6:55 pm

Nonstop0h 45m

$90

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Tue 4/14

10:10 am-10:55 am

Nonstop0h 45m

$96

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 19 results
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.

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 4h. Southwest provides one of the quickest options available for as low as $224. 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.

See more FAQs

Traveling to a place near Milwaukee?

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

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