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$109+ Cheap flights from Milwaukee (MKE) to Midway (MDW)

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 3/16. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MDW
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Milwaukee to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Milwaukee (MKE) to Midway (MDW). 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 September 17, 2025.

Round-trip from

$219
(Southwest)

One-way from

$110
(Southwest)

Popular in

November

Cheapest in

June

Average price

$239
From Milwaukee-Mitchell to Chicago Midway
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One-way flight from Milwaukee-Mitchell to Chicago Midway
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Highest demand for flights based on searches. 13% potential increase in price ($45 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Milwaukee to Midway

Cheapest flights from Milwaukee to Midway
Explore the most affordable flight options available from Milwaukee to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Southwest deal was found by Cheapflights users on 9/15. 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 10/294:05 pmMKE - MDW
1 stop6h 00mSouthwest
Fri 11/146:45 amMDW - MKE
1 stop4h 20mSouthwest
Deal found 9/15$219
This Southwest deal was found by Cheapflights users on 9/17. 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 10/215:45 amMKE - MDW
1 stop4h 10mSouthwest
Tue 10/2110:55 amMDW - MKE
1 stop5h 00mSouthwest
Deal found 9/17$228
This Southwest deal was found by Cheapflights users on 9/16. 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 10/107:30 pmMKE - MDW
1 stop3h 45mSouthwest
Tue 10/145:55 pmMDW - MKE
1 stop4h 05mSouthwest
Deal found 9/16$258
This Southwest deal was found by Cheapflights users on 9/15. 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 11/255:50 amMKE - MDW
1 stop4h 15mSouthwest
Fri 11/289:30 amMDW - MKE
2 stops7h 55mSouthwest
Deal found 9/15$273
This Southwest deal was found by Cheapflights users on 9/15. 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 10/37:30 pmMKE - MDW
1 stop3h 45mSouthwest
Sun 10/56:50 amMDW - MKE
1 stop3h 30mSouthwest
Deal found 9/15$287
This Southwest deal was found by Cheapflights users on 9/16. 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 12/1811:50 amMKE - MDW
1 stop4h 00mSouthwest
Sun 1/47:55 amMDW - MKE
1 stop4h 00mSouthwest
Deal found 9/16$308
This Southwest deal was found by Cheapflights users on 9/16. 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 10/167:30 pmMKE - MDW
1 stop3h 45mSouthwest
Thu 10/236:55 pmMDW - MKE
1 stop3h 40mSouthwest
Deal found 9/16$310
This Southwest deal was found by Cheapflights users on 9/17. 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 10/214:05 pmMKE - MDW
1 stop6h 00mSouthwest
Wed 10/2210:10 amMDW - MKE
2 stops7h 25mSouthwest
Deal found 9/17$315
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/167:38 pmMKE - MDW
2 stops15h 35mMultiple Airlines
Thu 10/236:24 pmMDW - MKE
1 stop24h 54mMultiple Airlines
Deal found 9/16$316
This Southwest deal was found by Cheapflights users on 9/17. 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 10/27:30 pmMKE - MDW
1 stop3h 45mSouthwest
Mon 10/66:45 pmMDW - MKE
1 stop4h 40mSouthwest
Deal found 9/17$328
This Southwest deal was found by Cheapflights users on 9/15. 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 9/257:55 amMKE - MDW
1 stop5h 00mSouthwest
Tue 9/306:25 amMDW - MKE
1 stop5h 05mSouthwest
Deal found 9/15$329

Cheapflights Fare Finder

 
Customize your flight search to find flights from Milwaukee to Midway 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 September 17, 2025.
Use the filters below to find and compare flights from Milwaukee to Chicago Midway Airport that are best for you.

Fly from

Milwaukee

Fly to

Midway

Route

Depart

Return

Price

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Wed 10/29

5:45 am-9:55 am

1 stop4h 10m

Chicago Midway

Fri 11/14

6:45 am-11:05 am

1 stop4h 20m

$219

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Tue 10/21

5:45 am-9:55 am

1 stop4h 10m

Chicago Midway

Wed 10/22

5:45 am-11:30 am

1 stop5h 45m

$219

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Tue 11/25

5:50 am-10:05 am

1 stop4h 15m

Chicago Midway

Fri 11/28

7:00 pm-11:30 pm

1 stop4h 30m

$219

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Tue 10/21

5:45 am-9:55 am

1 stop4h 10m

Chicago Midway

Tue 10/21

10:55 am-3:55 pm

1 stop5h 00m

$228

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Fri 10/10

7:30 pm-11:15 pm

1 stop3h 45m

Chicago Midway

Tue 10/14

5:55 pm-10:00 pm

1 stop4h 05m

$258

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Fri 10/3

7:30 pm-11:15 pm

1 stop3h 45m

Chicago Midway

Sun 10/5

6:50 am-10:20 am

1 stop3h 30m

$287

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Thu 10/16

7:38 pm-11:13 am

2 stops15h 35m

Chicago Midway

Thu 10/23

6:24 pm-7:18 pm

1 stop24h 54m

$316

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Mon 3/16

4:55 pm-5:45 pm

Nonstop0h 50m

$109

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Mon 12/15

4:05 pm-8:30 pm

1 stop4h 25m

$110

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Sun 11/16

5:50 am-9:55 am

1 stop4h 05m

$110

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Showing 1-10 of 16 results
1
2

Best time to book a flight from Milwaukee to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Milwaukee 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 Milwaukee to Midway. 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 from for flights from Milwaukee to Chicago Midway?

    Located just 6.4 mi from the city center, Milwaukee-Mitchell is the airport most travelers will use when flying to Chicago Midway from Milwaukee. Booking flights from Milwaukee-Mitchell (MKE) to Chicago Midway should be relatively easy as there are 0 daily outbound flights to Chicago Midway from 0 different airlines.

  • How long is the flight from Milwaukee to Chicago Midway Airport?

    Departing from Milwaukee to Chicago Midway Airport will take you 4h 10m. The distance between Milwaukee and Chicago Midway Airport is about 80 mi.

  • Can I find deals for flights from Milwaukee to Midway that include hotel bookings?

    Yes. In addition to deals on Milwaukee to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Milwaukee to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Milwaukee to Midway.

  • Can I find deals for business class flights from Milwaukee to Midway?

    Yes. Cheapflights offers flight deals from Milwaukee to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Milwaukee to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Milwaukee to Chicago Midway Airport (average of $160). Flying from Milwaukee to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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