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$59+ 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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MKE
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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Find 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 November 6, 2025.

This Southwest deal was found by Cheapflights users on 11/5. 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 12/248:45 pmMDW - MSP
Nonstop1h 30mSouthwest
Wed 12/3112:25 pmMSP - MDW
Nonstop1h 30mSouthwest
Deal found 11/5$97
This Delta deal was found by Cheapflights users on 11/5. 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 12/39:59 amMDW - MSP
Nonstop1h 43mDelta
Wed 12/34:30 pmMSP - MDW
Nonstop1h 48mDelta
Deal found 11/5$101
This Southwest deal was found by Cheapflights users on 11/4. 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 12/108:50 amMDW - MSP
1 stop5h 55mSouthwest
Thu 12/115:35 pmMSP - MDW
Nonstop1h 40mSouthwest
Deal found 11/4$111
This Delta deal was found by Cheapflights users on 11/6. 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 12/127:02 pmMDW - MSP
Nonstop1h 43mDelta
Wed 12/174:30 pmMSP - MDW
Nonstop1h 48mDelta
Deal found 11/6$122
This Southwest deal was found by Cheapflights users on 11/5. 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 12/38:15 amMDW - MSP
Nonstop1h 35mSouthwest
Wed 12/31:50 pmMSP - MDW
1 stop6h 15mSouthwest
Deal found 11/5$127
This Southwest deal was found by Cheapflights users on 11/6. 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 12/1211:15 amMDW - MSP
Nonstop1h 30mSouthwest
Wed 12/176:30 amMSP - MDW
1 stop6h 15mSouthwest
Deal found 11/6$132
This Southwest deal was found by Cheapflights users on 11/5. 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 12/31:45 pmMDW - MSP
Nonstop1h 30mSouthwest
Thu 12/47:15 amMSP - MDW
Nonstop1h 45mSouthwest
Deal found 11/5$140
This Southwest deal was found by Cheapflights users on 11/4. 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 12/58:45 pmMDW - MSP
Nonstop1h 30mSouthwest
Mon 12/85:45 amMSP - MDW
1 stop5h 40mSouthwest
Deal found 11/4$142
This Southwest deal was found by Cheapflights users on 11/5. 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 12/51:45 pmMDW - MSP
Nonstop1h 30mSouthwest
Sun 12/710:05 amMSP - MDW
Nonstop1h 30mSouthwest
Deal found 11/5$143
This Southwest deal was found by Cheapflights users on 11/5. 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 12/412:15 pmMDW - MKE
1 stop4h 35mSouthwest
Thu 12/115:30 amMKE - MDW
1 stop7h 15mSouthwest
Deal found 11/5$219
This Southwest deal was found by Cheapflights users on 11/4. 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 12/310:05 amMDW - MKE
1 stop6h 45mSouthwest
Fri 12/54:05 pmMKE - MDW
1 stop4h 40mSouthwest
Deal found 11/4$239
This Delta deal was found by Cheapflights users on 11/6. 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.
Tue 12/91:50 pmMDW - DLH
1 stop5h 45mDelta
Sun 12/147:45 amDLH - MDW
1 stop5h 25mDelta
Deal found 11/6$243

Cheap flight deals from Midway to Wisconsin

Keep the following information in mind while searching for Midway to Wisconsin flight deals. Data was last updated November 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$97
(Southwest)

One-way from

$59
(Southwest)

Popular in

February

Cheapest in

November

Average price

$179
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
Highest demand for flights based on searches. 12% potential increase in price ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 November 6, 2025.
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

Wed 12/10

1:50 pm-3:30 pm

Nonstop1h 40m

Minneapolis St Paul

Thu 12/11

4:30 pm-6:18 pm

Nonstop1h 48m

$101

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Fri 12/5

1:45 pm-3:15 pm

Nonstop1h 30m

Minneapolis St Paul

Sun 12/7

10:05 am-11:35 am

Nonstop1h 30m

$143

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Thu 12/4

8:45 pm-10:15 pm

Nonstop1h 30m

Minneapolis St Paul

Sun 12/7

10:05 am-11:35 am

Nonstop1h 30m

$143

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Wed 12/10

5:15 pm-9:45 pm

1 stop4h 30m

Minneapolis St Paul

Thu 12/11

5:30 am-2:55 pm

1 stop9h 25m

$157

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Fri 12/5

8:45 pm-10:15 pm

Nonstop1h 30m

Minneapolis St Paul

Mon 12/8

5:30 am-11:25 am

1 stop5h 55m

$173

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Thu 1/15

8:05 am-9:40 am

Nonstop1h 35m

Minneapolis St Paul

Mon 1/19

4:15 pm-10:30 pm

1 stop6h 15m

$174

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Thu 12/11

8:50 am-2:45 pm

1 stop5h 55m

Minneapolis St Paul

Mon 12/15

5:45 am-12:35 pm

2 stops6h 50m

$188

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Thu 1/8

4:05 pm-5:35 pm

Nonstop1h 30m

Minneapolis St Paul

Sun 1/11

5:50 pm-7:25 pm

Nonstop1h 35m

$213

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Thu 12/4

12:15 pm-4:50 pm

1 stop4h 35m

Milwaukee-Mitchell

Thu 12/11

5:30 am-12:45 pm

1 stop7h 15m

$219

ChicagoGreen Bay

MDW - GRB

MDWGRB

Chicago Midway

Wed 4/22

1:00 pm-4:33 pm

1 stop3h 33m

Green Bay Austin-Straubel

Sat 4/25

11:53 am-6:05 pm

1 stop6h 12m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

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

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 November 6, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 53% on flights from Chicago Midway Airport to Wisconsin by exploring options for tickets in the afternoon.

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 $143, Delta can have you in Wisconsin from Chicago Midway Airport in 1h 30m. 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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