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$110+ 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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MKE
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
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 October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$224
(Southwest)

One-way from

$110
(Southwest)

Popular in

December

Cheapest in

November

Average price

$304
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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Highest demand for flights based on searches. 8% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 29, 2025.

This Southwest deal was found by Cheapflights users on 10/27. 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.
Thu 12/48:10 amMDW - MKE
1 stop7h 15mSouthwest
Sat 12/65:45 amMKE - MDW
1 stop6h 00mSouthwest
Deal found 10/27$224
This Southwest deal was found by Cheapflights users on 10/27. 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.
Thu 11/209:50 amMDW - MKE
1 stop5h 35mSouthwest
Sun 11/235:50 amMKE - MDW
1 stop4h 05mSouthwest
Deal found 10/27$258
This Southwest deal was found by Cheapflights users on 10/27. 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 12/264:20 pmMDW - MKE
1 stop6h 25mSouthwest
Thu 1/15:30 amMKE - MDW
1 stop4h 25mSouthwest
Deal found 10/27$288
This Southwest deal was found by Cheapflights users on 10/27. 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 11/147:00 pmMDW - MKE
1 stop4h 30mSouthwest
Sat 11/155:45 amMKE - MDW
1 stop6h 00mSouthwest
Deal found 10/27$297
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/206:20 amMDW - MKE
2 stops11h 42mMultiple Airlines
Sun 11/2312:35 pmMKE - MDW
1 stop28h 17mMultiple Airlines
Deal found 10/27$313
This Southwest deal was found by Cheapflights users on 10/28. 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 11/106:10 pmMDW - MKE
1 stop5h 15mSouthwest
Mon 11/245:50 amMKE - MDW
1 stop4h 05mSouthwest
Deal found 10/28$314
This Southwest deal was found by Cheapflights users on 10/26. 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.
Sun 11/25:45 amMDW - MKE
1 stop4h 20mSouthwest
Mon 11/35:30 amMKE - MDW
1 stop7h 15mSouthwest
Deal found 10/26$389
This Southwest deal was found by Cheapflights users on 10/28. 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 11/46:20 amMDW - MKE
1 stop5h 20mSouthwest
Thu 11/65:50 amMKE - MDW
1 stop4h 05mSouthwest
Deal found 10/28$409
This Southwest deal was found by Cheapflights users on 10/28. 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 10/3111:45 amMDW - MKE
1 stop3h 35mSouthwest
Wed 11/126:00 amMKE - MDW
1 stop5h 25mSouthwest
Deal found 10/28$442

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 October 29, 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 12/4

8:10 am-3:25 pm

1 stop7h 15m

Milwaukee-Mitchell

Sat 12/6

5:45 am-11:45 am

1 stop6h 00m

$224

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Thu 11/20

9:50 am-3:25 pm

1 stop5h 35m

Milwaukee-Mitchell

Sun 11/23

5:50 am-9:55 am

1 stop4h 05m

$258

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Fri 12/26

4:20 pm-10:45 pm

1 stop6h 25m

Milwaukee-Mitchell

Thu 1/1

5:30 am-9:55 am

1 stop4h 25m

$288

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Fri 11/14

7:00 pm-11:30 pm

1 stop4h 30m

Milwaukee-Mitchell

Sat 11/15

5:45 am-11:45 am

1 stop6h 00m

$297

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Thu 11/20

6:20 am-6:02 pm

2 stops11h 42m

Milwaukee-Mitchell

Sun 11/23

12:35 pm-4:52 pm

1 stop28h 17m

$313

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Mon 11/10

6:10 pm-11:25 pm

1 stop5h 15m

Milwaukee-Mitchell

Mon 11/24

5:50 am-9:55 am

1 stop4h 05m

$314

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Sun 11/2

5:45 am-10:05 am

1 stop4h 20m

Milwaukee-Mitchell

Mon 11/3

5:30 am-12:45 pm

1 stop7h 15m

$389

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Tue 11/4

6:20 am-11:40 am

1 stop5h 20m

Milwaukee-Mitchell

Thu 11/6

5:50 am-9:55 am

1 stop4h 05m

$409

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Sat 11/1

11:45 am-3:25 pm

1 stop3h 40m

Milwaukee-Mitchell

Mon 11/3

5:30 am-9:55 am

1 stop4h 25m

$547

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Sat 1/24

6:00 am-12:51 pm

2 stops30h 51m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 20 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 October.
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 7h 15m. 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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