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$79+ Cheap flights from Midway (MDW) to Wisconsin

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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MKE
Jun 19 — Jun 261
Fri 6/19
Fri 6/26
1 adult, Economy
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Cheap flight deals from Midway to Wisconsin

Cheapest flights from Midway to Wisconsin
Explore the most affordable flight options available from Midway to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 20, 2026.

This Southwest deal was found by Cheapflights users on 5/15. 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 6/304:30 pm
MDW
-
MSP
Nonstop1h 30m
Southwest
Wed 7/17:55 am
MSP
-
MDW
1 stop4h 30m
Southwest
Deal found 5/15$147
This Southwest deal was found by Cheapflights users on 5/18. 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.
Tue 6/92:50 pm
MDW
-
MSP
Nonstop1h 30m
Southwest
Tue 6/167:05 am
MSP
-
MDW
2 stops6h 30m
Southwest
Deal found 5/18$152
This Southwest deal was found by Cheapflights users on 5/16. 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.
Wed 6/107:40 am
MDW
-
MSP
Nonstop1h 30m
Southwest
Wed 6/173:10 pm
MSP
-
MDW
1 stop8h 00m
Southwest
Deal found 5/16$153
This Southwest deal was found by Cheapflights users on 5/17. 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 6/235:10 pm
MDW
-
MSP
1 stop5h 35m
Southwest
Tue 6/303:10 pm
MSP
-
MDW
1 stop6h 00m
Southwest
Deal found 5/17$157
This Southwest deal was found by Cheapflights users on 5/18. 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.
Tue 6/95:20 pm
MDW
-
MSP
1 stop6h 35m
Southwest
Wed 6/107:05 am
MSP
-
MDW
2 stops6h 30m
Southwest
Deal found 5/18$162
This Southwest deal was found by Cheapflights users on 5/18. 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 9/94:40 pm
MDW
-
MSP
1 stop5h 40m
Southwest
Thu 9/107:40 am
MSP
-
MDW
Nonstop1h 30m
Southwest
Deal found 5/18$167
This Southwest deal was found by Cheapflights users on 5/15. 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 10/273:50 pm
MDW
-
MSP
1 stop6h 35m
Southwest
Thu 10/298:00 am
MSP
-
MDW
1 stop7h 10m
Southwest
Deal found 5/15$172
This Southwest deal was found by Cheapflights users on 5/17. 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 8/2710:05 am
MDW
-
MSP
Nonstop1h 30m
Southwest
Sat 8/293:20 pm
MSP
-
MDW
Nonstop1h 30m
Southwest
Deal found 5/17$177
This Southwest deal was found by Cheapflights users on 5/15. 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 8/44:40 pm
MDW
-
MSP
1 stop5h 40m
Southwest
Sat 8/88:05 am
MSP
-
MDW
1 stop8h 00m
Southwest
Deal found 5/15$182
This Delta deal was found by Cheapflights users on 5/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/241:49 pm
MDW
-
MSP
Nonstop1h 44m
Delta
Thu 7/26:04 am
MSP
-
MDW
1 stop6h 42m
Delta
Deal found 5/15$192
This Southwest deal was found by Cheapflights users on 5/15. 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 9/172:25 pm
MDW
-
MSP
Nonstop1h 30m
Southwest
Thu 9/247:55 am
MSP
-
MDW
1 stop7h 30m
Southwest
Deal found 5/15$193
This Southwest deal was found by Cheapflights users on 5/18. 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.
Tue 7/79:10 pm
MDW
-
MKE
Nonstop0h 50m
Southwest
Wed 7/86:00 am
MKE
-
MDW
Nonstop0h 50m
Southwest
Deal found 5/18$197

Find flight deals from Midway to Wisconsin

Keep the following information in mind while searching for Midway to Wisconsin flight deals. Data was last updated May 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$147
(Southwest)

One-way from

$79
(Southwest)
Provider with most accurate pricing for Chicago (CHI)-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Milwaukee-Mitchell flights.
Search Deals
From Chicago Midway to Wisconsin
Search Deals
One-way flight from Chicago Midway to Wisconsin
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Wisconsin 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 May 20, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Wisconsin that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Tue 7/7

9:10 pm-10:00 pm

Nonstop0h 50m

Milwaukee-Mitchell

Wed 7/8

6:00 am-6:50 am

Nonstop0h 50m

$197

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Sat 8/8

10:15 am-11:05 am

Nonstop0h 50m

Milwaukee-Mitchell

Wed 8/12

3:40 pm-4:30 pm

Nonstop0h 50m

$207
Quickest round-trip

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Tue 6/9

10:10 am-10:55 am

Nonstop0h 45m

Milwaukee-Mitchell

Thu 6/11

5:40 am-6:30 am

Nonstop0h 50m

$208

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Fri 7/17

9:55 pm-10:45 pm

Nonstop0h 50m

Milwaukee-Mitchell

Tue 7/21

6:00 am-6:50 am

Nonstop0h 50m

$208

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Thu 6/4

10:20 am-11:05 am

Nonstop0h 45m

Milwaukee-Mitchell

Wed 6/10

5:05 pm-10:35 pm

1 stop5h 30m

$217

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Thu 6/11

9:55 pm-10:45 pm

Nonstop0h 50m

Milwaukee-Mitchell

Sun 6/14

6:00 am-6:50 am

Nonstop0h 50m

$219

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Fri 6/12

9:55 pm-10:45 pm

Nonstop0h 50m

Milwaukee-Mitchell

Fri 6/19

5:15 pm-6:05 pm

Nonstop0h 50m

$219

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Wed 7/1

7:16 pm-8:59 pm

Nonstop1h 43m

Minneapolis St Paul

Sun 7/5

6:55 am-8:37 am

Nonstop1h 42m

$226

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Tue 7/28

1:49 pm-3:33 pm

Nonstop1h 44m

Minneapolis St Paul

Thu 7/30

6:55 am-8:37 am

Nonstop1h 42m

$226

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Sat 7/25

9:19 am-1:11 pm

1 stop3h 52m

Minneapolis St Paul

Tue 7/28

4:40 pm-6:18 pm

Nonstop1h 38m

$236

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/18

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Midway to Wisconsin

Have a flexible travel schedule? Discover the best time to fly to Wisconsin 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.

Cheapflights Insights

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

What is the cheapest time of day to fly from MDW to WI?

Find hourly flight availability from Midway to Wisconsin. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 20, 2026.

When flying from Chicago Midway Airport to Wisconsin, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Related info for your journey

Find useful and relevant information for your journey from Midway to Wisconsin. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    For as low as $197, Southwest can have you in Wisconsin from Chicago Midway Airport in 50m. Chicago Midway Airport and Wisconsin are separated by a distance of 80 mi. Most flights are nonstop.

  • What are the most popular routes from Chicago Midway Airport to Wisconsin?

    When deciding which route to take from Chicago Midway Airport to Wisconsin consider Chicago Midway - Minneapolis St Paul, Chicago Midway - Duluth Intl or Chicago Midway - Rhinelander Oneida County as they are the most popular.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Wisconsin 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

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Alternative routes for Midway to Wisconsin

See prices for flight routes from nearby airports that may be better suited for you.
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Midway to LaGuardia flights
Midway to John F Kennedy Intl flights
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Midway to Tampa flights
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Midway to San Francisco flights
O'Hare Intl to Portland flights
Midway to Seattle flights
Midway to Denver flights
O'Hare Intl to Reagan-National flights
Midway to Fort Lauderdale flights
O'Hare Intl to Bozeman flights
O'Hare Intl to Raleigh flights

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