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$100+ 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MKE
Jan 2 — Jan 91
Fri 1/2
Fri 1/9
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 December 3, 2025.

This Southwest deal was found by Cheapflights users on 12/2. 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 12/116:20 amMDW - MKE
1 stop5h 20mSouthwest
Fri 12/125:50 amMKE - MDW
1 stop4h 05mSouthwest
Deal found 12/2$284
This Southwest deal was found by Cheapflights users on 12/3. 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 12/135:50 amMDW - MKE
1 stop4h 05mSouthwest
Sat 12/131:10 pmMKE - MDW
1 stop5h 55mSouthwest
Deal found 12/3$309
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/113:10 pmMDW - MKE
1 stop18h 29mMultiple Airlines
Sun 12/146:09 pmMKE - MDW
2 stops38h 37mMultiple Airlines
Deal found 12/3$338
This Southwest deal was found by Cheapflights users on 12/3. 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 12/45:15 pmMDW - MKE
1 stop4h 15mSouthwest
Thu 12/114:05 pmMKE - MDW
1 stop4h 40mSouthwest
Deal found 12/3$339
This Southwest deal was found by Cheapflights users on 12/1. 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 12/256:35 amMDW - MKE
1 stop5h 25mSouthwest
Sun 12/285:50 amMKE - MDW
1 stop4h 15mSouthwest
Deal found 12/1$347
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/113:10 pmMDW - MKE
1 stop25h 59mMultiple Airlines
Mon 12/1510:34 amMKE - MDW
2 stops22h 12mMultiple Airlines
Deal found 12/3$385
This Kiwi.com deal was found by Cheapflights users on 12/1. 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 12/46:15 amMDW - MKE
2 stops27h 24mMultiple Airlines
Mon 12/810:34 amMKE - MDW
1 stop11h 24mMultiple Airlines
Deal found 12/1$388
This Southwest deal was found by Cheapflights users on 12/2. 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 12/45:15 pmMDW - MKE
1 stop4h 15mSouthwest
Fri 12/54:05 pmMKE - MDW
1 stop4h 40mSouthwest
Deal found 12/2$389
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 12/113:10 pmMDW - MKE
1 stop18h 29mMultiple Airlines
Fri 12/126:09 pmMKE - MDW
2 stops27h 13mMultiple Airlines
Deal found 12/2$395
This Kiwi.com deal was found by Cheapflights users on 11/30. 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.
Sun 12/146:37 pmMDW - MKE
1 stop15h 02mMultiple Airlines
Thu 12/188:15 pmMKE - MDW
1 stop25h 43mMultiple Airlines
Deal found 11/30$408

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 December 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$208
(Southwest)

One-way from

$100
(Southwest)

Popular in

February

Cheapest in

November

Average price

$394
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
Highest demand for flights based on searches. 13% potential increase in price ($43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 3, 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

Thu 3/12

11:00 am-11:45 am

Nonstop0h 45m

Milwaukee-Mitchell

Wed 3/18

5:50 am-6:50 am

Nonstop1h 00m

$208

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Fri 2/13

7:55 am-12:15 pm

1 stop4h 20m

Milwaukee-Mitchell

Tue 2/17

5:25 am-10:20 am

1 stop4h 55m

$222

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Sat 12/13

5:50 am-9:55 am

1 stop4h 05m

Milwaukee-Mitchell

Sat 12/13

1:10 pm-7:05 pm

1 stop5h 55m

$309

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Thu 12/25

6:35 am-12:00 pm

1 stop5h 25m

Milwaukee-Mitchell

Sun 12/28

5:50 am-10:05 am

1 stop4h 15m

$347

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Sun 12/14

6:37 pm-9:39 am

1 stop15h 02m

Milwaukee-Mitchell

Thu 12/18

8:15 pm-9:58 pm

1 stop25h 43m

$408

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Wed 12/24

11:48 am-9:35 pm

1 stop9h 47m

Milwaukee-Mitchell

Thu 12/25

6:25 am-5:19 pm

1 stop10h 54m

$445

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Thu 3/12

3:10 pm-10:02 am

1 stop18h 52m

Milwaukee-Mitchell

Wed 3/18

6:09 pm-11:33 am

2 stops17h 24m

$582

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Mon 5/4

5:40 pm-11:00 pm

1 stop5h 20m

$110

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Mon 3/2

8:56 pm-5:04 pm

1 stop20h 08m

$112

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Tue 2/3

1:20 pm-6:01 pm

2 stops28h 41m

$113

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/2

Showing 1-10 of 16 results
1
2

Compare providers for flights from Midway to Milwaukee

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Milwaukee in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Milwaukee flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Milwaukee flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 45m. Southwest provides one of the quickest options available for as low as $208. 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
New Berlin
Oak Creek
Wauwatosa

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