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$90+ 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 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MDW
Feb 13 — Feb 201
Fri 2/13
Fri 2/20
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 January 14, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$199
(Southwest)

One-way from

$90
(Southwest)

Popular in

January

Cheapest in

June

Average price

$361

Good round-trip deal

$374 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. 9% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 14, 2026.

This Southwest deal was found by Cheapflights users on 1/14. 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 2/235:25 am
MKE
-
MDW
1 stop4h 55m
Southwest
Wed 2/256:10 am
MDW
-
MKE
1 stop5h 20m
Southwest
Deal found 1/14$199
This Southwest deal was found by Cheapflights users on 1/12. 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 2/113:50 pm
MKE
-
MDW
1 stop3h 15m
Southwest
Wed 2/186:00 am
MDW
-
MKE
1 stop5h 55m
Southwest
Deal found 1/12$209
This Southwest deal was found by Cheapflights users on 1/13. 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 8/266:40 am
MKE
-
MDW
Nonstop0h 50m
Southwest
Sun 8/306:15 pm
MDW
-
MKE
Nonstop0h 50m
Southwest
Deal found 1/13$219
This Southwest deal was found by Cheapflights users on 1/11. 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.
Tue 2/103:50 pm
MKE
-
MDW
1 stop3h 15m
Southwest
Tue 2/1711:00 am
MDW
-
MKE
1 stop5h 20m
Southwest
Deal found 1/11$239
This Southwest deal was found by Cheapflights users on 1/12. 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 2/56:35 pm
MKE
-
MDW
1 stop3h 05m
Southwest
Sat 2/145:15 pm
MDW
-
MKE
1 stop5h 10m
Southwest
Deal found 1/12$248
This Southwest deal was found by Cheapflights users on 1/13. 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 8/128:20 am
MKE
-
MDW
1 stop3h 30m
Southwest
Sun 8/166:15 pm
MDW
-
MKE
Nonstop0h 50m
Southwest
Deal found 1/13$258
This Southwest deal was found by Cheapflights users on 1/14. 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 1/316:30 am
MKE
-
MDW
1 stop5h 05m
Southwest
Sun 2/18:15 am
MDW
-
MKE
1 stop3h 15m
Southwest
Deal found 1/14$259
This Southwest deal was found by Cheapflights users on 1/11. 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 1/215:30 am
MKE
-
MDW
1 stop4h 00m
Southwest
Sat 1/242:40 pm
MDW
-
MKE
1 stop5h 50m
Southwest
Deal found 1/11$261
This Southwest deal was found by Cheapflights users on 1/12. 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 2/95:25 am
MKE
-
MDW
1 stop4h 55m
Southwest
Mon 2/165:25 am
MDW
-
MKE
1 stop5h 50m
Southwest
Deal found 1/12$268
This Southwest deal was found by Cheapflights users on 1/13. 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 2/55:25 am
MKE
-
MDW
1 stop4h 55m
Southwest
Sun 2/81:50 pm
MDW
-
MKE
1 stop7h 20m
Southwest
Deal found 1/13$273

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 January 14, 2026.
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

Mon 2/23

5:25 am-10:20 am

1 stop4h 55m

Chicago Midway

Wed 2/25

6:10 am-11:30 am

1 stop5h 20m

$199

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Wed 2/11

3:50 pm-7:05 pm

1 stop3h 15m

Chicago Midway

Wed 2/18

6:00 am-11:55 am

1 stop5h 55m

$209

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Tue 2/10

5:30 am-9:30 am

1 stop4h 00m

Chicago Midway

Tue 2/17

11:00 am-4:20 pm

1 stop5h 20m

$239

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Thu 2/5

6:35 pm-9:40 pm

1 stop3h 05m

Chicago Midway

Sat 2/14

5:15 pm-10:25 pm

1 stop5h 10m

$248

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Sat 1/31

6:30 am-11:35 am

1 stop5h 05m

Chicago Midway

Sun 2/1

8:15 am-11:30 am

1 stop3h 15m

$259

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Wed 1/21

5:30 am-9:30 am

1 stop4h 00m

Chicago Midway

Sat 1/24

2:40 pm-8:30 pm

1 stop5h 50m

$261

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Mon 2/9

5:25 am-10:20 am

1 stop4h 55m

Chicago Midway

Mon 2/16

5:25 am-11:15 am

1 stop5h 50m

$268

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Sat 2/14

3:20 pm-7:55 pm

1 stop4h 35m

Chicago Midway

Sun 2/15

11:00 am-4:20 pm

1 stop5h 20m

$298

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Thu 2/5

5:25 am-10:20 am

1 stop4h 55m

Chicago Midway

Sun 2/8

1:25 pm-7:55 pm

2 stops6h 30m

$302

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Fri 3/20

5:50 am-6:50 am

Nonstop1h 00m

Chicago Midway

Sun 3/22

10:10 am-10:55 am

Nonstop0h 45m

$307

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/12

Showing 1-10 of 18 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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 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 25% of weekly flights between Milwaukee and Chicago have experienced delays in the past year, with the average delay time being 89 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 in the evening 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, Braathens Regional Aviation have had the lowest number of delays on this route, with just 11% of flights being 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 55m. 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 $406, our data shows the cheapest flight currently is $248. When looking at the most popular route, (Milwaukee-Mitchell - Chicago Midway), you can expect to pay $239 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
Merrillville
Hammond
Porter
Benton Harbor

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