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$64+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MKE
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
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 January 28, 2026.

This Southwest deal was found by Cheapflights users on 1/27. 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 2/1912:25 pm
MDW
-
MSP
Nonstop1h 30m
Southwest
Tue 2/247:20 am
MSP
-
MDW
Nonstop1h 55m
Southwest
Deal found 1/27$134
This Southwest deal was found by Cheapflights users on 1/27. 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 2/267:55 am
MDW
-
MSP
1 stop3h 30m
Southwest
Tue 3/36:50 am
MSP
-
MDW
1 stop6h 35m
Southwest
Deal found 1/27$154
This Southwest deal was found by Cheapflights users on 1/27. 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.
Tue 2/241:50 pm
MDW
-
MSP
1 stop8h 00m
Southwest
Sat 2/281:45 pm
MSP
-
MDW
1 stop6h 10m
Southwest
Deal found 1/27$159
This Southwest deal was found by Cheapflights users on 1/27. 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.
Wed 2/258:40 am
MDW
-
MSP
Nonstop1h 40m
Southwest
Wed 2/252:30 pm
MSP
-
MDW
1 stop7h 20m
Southwest
Deal found 1/27$167
This Southwest deal was found by Cheapflights users on 1/27. 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 2/1912:25 pm
MDW
-
MSP
Nonstop1h 30m
Southwest
Mon 2/237:00 am
MSP
-
MDW
Nonstop1h 50m
Southwest
Deal found 1/27$171
This Southwest deal was found by Cheapflights users on 1/24. 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 2/198:50 pm
MDW
-
MSP
Nonstop1h 30m
Southwest
Sat 2/2110:10 am
MSP
-
MDW
Nonstop1h 40m
Southwest
Deal found 1/24$176
This Delta deal was found by Cheapflights users on 1/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/139:30 am
MDW
-
MSP
Nonstop1h 37m
Delta
Mon 3/165:07 pm
MSP
-
MDW
Nonstop1h 33m
Delta
Deal found 1/26$181
This Southwest deal was found by Cheapflights users on 1/26. 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.
Mon 4/204:05 pm
MDW
-
MSP
Nonstop1h 30m
Southwest
Wed 5/138:40 am
MSP
-
MDW
2 stops7h 55m
Southwest
Deal found 1/26$186
This Expedia deal was found by Cheapflights users on 1/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:30 am
MDW
-
MSP
1 stop12h 02m
Frontier
Sun 3/18:17 pm
MSP
-
MDW
1 stop24h 10m
Frontier
Deal found 1/25$189
This Southwest deal was found by Cheapflights users on 1/27. 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.
Tue 2/2410:05 am
MDW
-
MKE
1 stop6h 55m
Southwest
Tue 3/33:50 pm
MKE
-
MDW
1 stop3h 15m
Southwest
Deal found 1/27$208
This Delta deal was found by Cheapflights users on 1/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/202:05 pm
MDW
-
DLH
1 stop6h 04m
Delta
Mon 3/2312:37 pm
DLH
-
MDW
1 stop6h 03m
Delta
Deal found 1/27$228
This Delta deal was found by Cheapflights users on 1/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/119:53 am
MDW
-
GRB
1 stop5h 44m
Delta
Sun 2/157:00 am
GRB
-
MDW
1 stop5h 46m
Delta
Deal found 1/27$229

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 January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$134
(Southwest)

One-way from

$64
(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 January 28, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Wisconsin that are best for you.

Fly from

Midway

Fly to

Wisconsin

Route

Depart

Return

Price

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Thu 2/26

10:15 pm-11:40 pm

Nonstop1h 25m

Minneapolis St Paul

Tue 3/3

2:30 pm-9:50 pm

1 stop7h 20m

$144

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Wed 4/22

9:31 am-11:10 am

Nonstop1h 39m

Minneapolis St Paul

Wed 5/13

11:30 am-1:07 pm

Nonstop1h 37m

$171

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Wed 2/18

1:49 pm-3:35 pm

Nonstop1h 46m

Minneapolis St Paul

Tue 2/24

11:20 am-1:05 pm

Nonstop1h 45m

$171

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Mon 4/20

9:31 am-11:10 am

Nonstop1h 39m

Minneapolis St Paul

Wed 5/13

11:30 am-1:07 pm

Nonstop1h 37m

$171

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Mon 4/20

9:31 am-11:10 am

Nonstop1h 39m

Minneapolis St Paul

Tue 5/12

7:00 am-8:38 am

Nonstop1h 38m

$171

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Thu 2/19

1:49 pm-3:35 pm

Nonstop1h 46m

Minneapolis St Paul

Sat 2/21

2:30 pm-4:14 pm

Nonstop1h 44m

$171

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Thu 2/19

8:50 pm-10:20 pm

Nonstop1h 30m

Minneapolis St Paul

Sat 2/21

10:10 am-11:50 am

Nonstop1h 40m

$176

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Thu 2/19

8:05 am-9:40 am

Nonstop1h 35m

Minneapolis St Paul

Mon 2/23

5:20 am-10:20 am

1 stop5h 00m

$181

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Mon 4/6

7:20 pm-9:00 pm

Nonstop1h 40m

Minneapolis St Paul

Thu 4/9

7:00 am-8:50 am

Nonstop1h 50m

$181

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Thu 4/9

9:30 am-11:07 am

Nonstop1h 37m

Minneapolis St Paul

Fri 4/10

7:00 am-8:50 am

Nonstop1h 50m

$181

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 60 results
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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
No data available for this route at this time. Please check back soon.

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 $144, Southwest can have you in Wisconsin from Chicago Midway Airport in 1h 25m. Chicago Midway Airport and Wisconsin are separated by a distance of 348 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 - Milwaukee-Mitchell 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 Tampa flights
Midway to John F Kennedy Intl flights
Midway to Denver flights
Midway to Atlanta flights
O'Hare Intl to Jacksonville flights
O'Hare Intl to Love Field flights

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