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$89+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MDW
Dec 18 — Dec 251
Thu 12/18
Thu 12/25
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 November 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$229
(Southwest)

One-way from

$89
(Kiwi.com)

Popular in

January

Cheapest in

June

Average price

$334

Good round-trip deal

$386 or less
Provider with most accurate pricing for Milwaukee-Mitchell-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Chicago Midway flights.
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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. 11% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from Milwaukee-Mitchell to Chicago Midway.
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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 November 18, 2025.

This Southwest deal was found by Cheapflights users on 11/17. 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.
Sun 12/75:50 amMKE - MDW
1 stop4h 05mSouthwest
Sun 12/146:45 amMDW - MKE
1 stop4h 20mSouthwest
Deal found 11/17$244
This Southwest deal was found by Cheapflights users on 11/17. 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.
Wed 12/178:35 amMKE - MDW
1 stop4h 05mSouthwest
Wed 12/248:25 amMDW - MKE
1 stop3h 15mSouthwest
Deal found 11/17$248
This Southwest deal was found by Cheapflights users on 11/15. 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 12/44:05 pmMKE - MDW
1 stop4h 40mSouthwest
Sun 12/77:20 pmMDW - MKE
1 stop4h 10mSouthwest
Deal found 11/15$263
This Southwest deal was found by Cheapflights users on 11/15. 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.
Sat 12/135:45 amMKE - MDW
1 stop6h 00mSouthwest
Sat 12/205:35 pmMDW - MKE
1 stop6h 50mSouthwest
Deal found 11/15$278
This Southwest deal was found by Cheapflights users on 11/17. 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 11/255:50 amMKE - MDW
1 stop4h 15mSouthwest
Fri 11/286:45 amMDW - MKE
1 stop4h 20mSouthwest
Deal found 11/17$284
This Southwest deal was found by Cheapflights users on 11/17. 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.
Wed 12/249:05 amMKE - MDW
1 stop3h 35mSouthwest
Wed 12/245:15 pmMDW - MKE
1 stop4h 15mSouthwest
Deal found 11/17$333
This Southwest deal was found by Cheapflights users on 11/18. 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 11/194:05 pmMKE - MDW
1 stop4h 40mSouthwest
Thu 11/209:50 amMDW - MKE
1 stop5h 35mSouthwest
Deal found 11/18$340
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:09 pmMKE - MDW
2 stops38h 37mMultiple Airlines
Sun 12/146:37 pmMDW - MKE
1 stop15h 02mMultiple Airlines
Deal found 11/17$379
This Delta deal was found by Cheapflights users on 11/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/107:10 amMKE - MDW
1 stop10h 50mDelta
Sat 12/131:14 pmMDW - MKE
1 stop7h 16mDelta
Deal found 11/17$559

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 November 18, 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

Fri 12/12

5:50 am-9:55 am

1 stop4h 05m

Chicago Midway

Sun 12/14

6:45 am-11:05 am

1 stop4h 20m

$229

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Sun 12/7

5:50 am-9:55 am

1 stop4h 05m

Chicago Midway

Sun 12/14

6:45 am-11:05 am

1 stop4h 20m

$244

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Wed 12/17

8:35 am-12:40 pm

1 stop4h 05m

Chicago Midway

Wed 12/24

8:25 am-11:40 am

1 stop3h 15m

$248

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Thu 12/4

4:05 pm-8:45 pm

1 stop4h 40m

Chicago Midway

Sun 12/7

7:20 pm-11:30 pm

1 stop4h 10m

$263

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Sat 12/13

5:45 am-11:45 am

1 stop6h 00m

Chicago Midway

Sat 12/20

5:35 pm-12:25 am

1 stop6h 50m

$278

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Wed 12/24

9:05 am-12:40 pm

1 stop3h 35m

Chicago Midway

Wed 12/24

5:15 pm-9:30 pm

1 stop4h 15m

$333

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Fri 12/12

10:34 am-10:12 pm

2 stops11h 38m

Chicago Midway

Sun 12/14

6:37 pm-9:39 am

1 stop15h 02m

$375

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Sun 12/7

6:09 pm-8:46 am

2 stops38h 37m

Chicago Midway

Sun 12/14

6:37 pm-9:39 am

1 stop15h 02m

$379

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Wed 12/10

9:40 am-6:00 pm

1 stop8h 20m

Chicago Midway

Sat 12/13

6:46 pm-8:45 am

1 stop13h 59m

$559

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Sat 1/17

7:42 pm-5:05 pm

1 stop21h 23m

$89

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/17

Showing 1-10 of 20 results
1
2

Compare providers for flights from Milwaukee to Midway

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 Milwaukee to Midway in November.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 Milwaukee-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Milwaukee-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Milwaukee-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Milwaukee-Chicago Midway Airport 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 Milwaukee-Chicago Midway Airport 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 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.

Cheapflights Insights

Everything you need to know about your flight from Milwaukee to Chicago Midway Airport

How often are flights from Milwaukee to Chicago delayed?

About 21% of weekly flights between Milwaukee and Chicago have experienced delays in the past year, with the average delay time being 79 minutes.

What is the most punctual flight time for Milwaukee to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Milwaukee to Chicago flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with no flights being classified as delayed.

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 05m. The distance between Milwaukee and Chicago Midway Airport is about 80 mi.

  • What are the cheapest flights from Milwaukee to Chicago Midway Airport?

    While on average a flight from Milwaukee to Chicago Midway Airport is generally $399, our data shows the cheapest flight currently is $386. When looking at the most popular route, (Milwaukee-Mitchell - Chicago Midway), you can expect to pay $244 for that flight.

  • 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.

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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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