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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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MKE
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
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 12, 2025.

This Southwest deal was found by Cheapflights users on 12/11. 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.
Mon 12/227:55 amMDW - MKE
1 stop4h 00mSouthwest
Fri 1/25:50 amMKE - MDW
1 stop4h 15mSouthwest
Deal found 12/11$334
This Southwest deal was found by Cheapflights users on 12/11. 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.
Wed 12/175:15 pmMDW - MKE
1 stop4h 15mSouthwest
Sun 12/216:30 pmMKE - MDW
1 stop3h 15mSouthwest
Deal found 12/11$339
This Southwest deal was found by Cheapflights users on 12/10. 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.
Tue 12/237:55 amMDW - MKE
1 stop4h 00mSouthwest
Wed 12/316:00 amMKE - MDW
1 stop5h 25mSouthwest
Deal found 12/10$353
This Southwest deal was found by Cheapflights users on 12/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:20 amMDW - MKE
1 stop4h 15mSouthwest
Mon 12/154:05 pmMKE - MDW
1 stop4h 40mSouthwest
Deal found 12/9$364
This Southwest deal was found by Cheapflights users on 12/10. 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.
Sat 12/203:00 pmMDW - MKE
1 stop3h 45mSouthwest
Sun 12/216:30 pmMKE - MDW
1 stop3h 15mSouthwest
Deal found 12/10$416
This Southwest deal was found by Cheapflights users on 12/10. 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.
Wed 12/248:25 amMDW - MKE
1 stop3h 15mSouthwest
Wed 12/244:05 pmMKE - MDW
1 stop4h 10mSouthwest
Deal found 12/10$431
This Southwest deal was found by Cheapflights users on 12/10. 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.
Fri 12/197:55 amMDW - MKE
1 stop4h 00mSouthwest
Sun 12/285:50 amMKE - MDW
1 stop4h 15mSouthwest
Deal found 12/10$453
This Kiwi.com deal was found by Cheapflights users on 12/11. 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.
Fri 12/263:10 pmMDW - MKE
1 stop27h 53mMultiple Airlines
Tue 12/307:21 pmMKE - MDW
2 stops46h 17mMultiple Airlines
Deal found 12/11$649
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/263:10 pmMDW - MKE
1 stop27h 53mFrontier
Tue 12/307:21 pmMKE - MDW
1 stop26h 37mFrontier
Deal found 12/10$685
This Kiwi.com deal was found by Cheapflights users on 12/11. 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.
Mon 12/223:10 pmMDW - MKE
1 stop27h 16mFrontier
Fri 1/210:48 amMKE - MDW
2 stops11h 10mFrontier
Deal found 12/11$879

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 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$228
(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. 17% potential increase in price ($56 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% 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 12, 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 3/5

9:45 pm-10:30 pm

Nonstop0h 45m

Milwaukee-Mitchell

Sun 3/8

4:40 pm-5:30 pm

Nonstop0h 50m

$228

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Thu 1/1

5:15 pm-9:30 pm

1 stop4h 15m

Milwaukee-Mitchell

Sun 1/4

5:50 am-10:05 am

1 stop4h 15m

$285

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Fri 1/9

6:10 am-11:30 am

1 stop5h 20m

Milwaukee-Mitchell

Fri 1/16

6:35 pm-9:40 pm

1 stop3h 05m

$317

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Mon 12/22

7:55 am-11:55 am

1 stop4h 00m

Milwaukee-Mitchell

Fri 1/2

5:50 am-10:05 am

1 stop4h 15m

$334

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Wed 12/17

5:15 pm-9:30 pm

1 stop4h 15m

Milwaukee-Mitchell

Sun 12/21

6:30 pm-9:45 pm

1 stop3h 15m

$339

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Thu 3/5

3:00 pm-11:41 am

2 stops20h 41m

Milwaukee-Mitchell

Sun 3/8

9:01 pm-1:08 pm

1 stop16h 07m

$343

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Tue 12/23

7:55 am-11:55 am

1 stop4h 00m

Milwaukee-Mitchell

Wed 12/31

6:00 am-11:25 am

1 stop5h 25m

$353

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Thu 1/1

5:15 pm-9:30 pm

1 stop4h 15m

Milwaukee-Mitchell

Sat 1/3

2:35 pm-7:40 pm

1 stop5h 05m

$404

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Sat 12/20

3:00 pm-6:45 pm

1 stop3h 45m

Milwaukee-Mitchell

Sun 12/21

6:30 pm-9:45 pm

1 stop3h 15m

$416

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Wed 12/24

8:25 am-11:40 am

1 stop3h 15m

Milwaukee-Mitchell

Wed 12/24

4:05 pm-8:15 pm

1 stop4h 10m

$431

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 22 results
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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 $228. 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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