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$49+ 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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MKE
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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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 September 16, 2025.

Round-trip from

$97
(Southwest)

One-way from

$49
(Delta)

Popular in

December

Cheapest in

September

Average price

$181
From Chicago Midway to Wisconsin
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One-way flight from Chicago Midway to Wisconsin
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Highest demand for flights based on searches. 26% potential increase in price ($97 potential increase over avg. RT price).
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Cheapest flight prices on average. 11% potential price decrease ($29 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 16, 2025.

This Delta deal was found by Cheapflights users on 9/15. 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 10/159:20 amMDW - MSP
Nonstop1h 42mDelta
Wed 10/224:08 pmMSP - MDW
Nonstop1h 35mDelta
Deal found 9/15$97
This Southwest deal was found by Cheapflights users on 9/15. 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.
Wed 10/156:35 pmMDW - MSP
Nonstop1h 30mSouthwest
Wed 10/226:00 amMSP - MDW
1 stop3h 55mSouthwest
Deal found 9/15$107
This Southwest deal was found by Cheapflights users on 9/15. 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 10/237:45 amMDW - MSP
Nonstop1h 25mSouthwest
Sat 10/258:00 amMSP - MDW
2 stops8h 25mSouthwest
Deal found 9/15$112
This Southwest deal was found by Cheapflights users on 9/16. 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.
Tue 11/118:25 amMDW - MSP
1 stop3h 25mSouthwest
Sat 11/155:20 amMSP - MDW
1 stop6h 25mSouthwest
Deal found 9/16$117
This Delta deal was found by Cheapflights users on 9/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/169:20 amMDW - MSP
Nonstop1h 42mDelta
Sun 10/197:15 amMSP - MDW
Nonstop1h 40mDelta
Deal found 9/16$120
This Southwest deal was found by Cheapflights users on 9/15. 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 10/215:55 pmMDW - MSP
1 stop4h 25mSouthwest
Thu 10/236:00 amMSP - MDW
1 stop9h 15mSouthwest
Deal found 9/15$122
This Southwest deal was found by Cheapflights users on 9/15. 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 10/119:50 amMDW - MSP
Nonstop1h 30mSouthwest
Sat 10/115:05 pmMSP - MDW
Nonstop1h 30mSouthwest
Deal found 9/15$130
This Southwest deal was found by Cheapflights users on 9/15. 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.
Wed 10/155:55 pmMDW - MSP
1 stop4h 25mSouthwest
Mon 10/205:15 amMSP - MDW
Nonstop1h 30mSouthwest
Deal found 9/15$140
This Southwest deal was found by Cheapflights users on 9/15. 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.
Fri 10/3112:40 pmMDW - MSP
Nonstop1h 30mSouthwest
Sun 11/25:45 amMSP - MDW
Nonstop1h 45mSouthwest
Deal found 9/15$143
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/294:48 pmMDW - MSP
1 stop7h 28mFrontier
Thu 10/212:25 pmMSP - MDW
1 stop11h 16mFrontier
Deal found 9/15$144
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3112:30 pmMDW - MSP
1 stop20h 50mFrontier
Sun 11/25:00 amMSP - MDW
1 stop5h 30mFrontier
Deal found 9/14$145
This Frontier deal was found by Cheapflights users on 9/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3112:30 pmMDW - MSP
1 stop11h 25mFrontier
Fri 11/711:29 amMSP - MDW
1 stop7h 10mFrontier
Deal found 9/16$146

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 September 16, 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 10/15

6:35 pm-8:05 pm

Nonstop1h 30m

Minneapolis St Paul

Mon 10/20

6:55 pm-8:25 pm

Nonstop1h 30m

$97

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Thu 10/16

9:20 am-11:02 am

Nonstop1h 42m

Minneapolis St Paul

Tue 10/21

4:08 pm-5:43 pm

Nonstop1h 35m

$97

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Thu 10/23

9:20 am-11:02 am

Nonstop1h 42m

Minneapolis St Paul

Sat 10/25

8:50 am-10:30 am

Nonstop1h 40m

$97

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Thu 10/23

6:55 pm-11:50 pm

1 stop4h 55m

Minneapolis St Paul

Sat 10/25

2:25 pm-3:55 pm

Nonstop1h 30m

$107

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Sat 10/18

9:20 am-11:02 am

Nonstop1h 42m

Minneapolis St Paul

Sun 10/19

7:15 am-8:55 am

Nonstop1h 40m

$120

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Sat 12/6

9:59 am-11:42 am

Nonstop1h 43m

Minneapolis St Paul

Sun 12/7

7:24 am-9:19 am

Nonstop1h 55m

$120

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Sat 10/25

7:10 pm-8:49 pm

Nonstop1h 39m

Minneapolis St Paul

Sun 10/26

7:15 am-8:55 am

Nonstop1h 40m

$120

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Sat 12/6

3:15 pm-4:45 pm

Nonstop1h 30m

Minneapolis St Paul

Sun 12/7

5:30 am-11:05 am

1 stop5h 35m

$130

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Sat 10/25

7:35 pm-9:00 pm

Nonstop1h 25m

Minneapolis St Paul

Sun 10/26

5:35 pm-12:10 am

1 stop6h 35m

$130

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Sat 10/11

7:35 pm-9:00 pm

Nonstop1h 25m

Minneapolis St Paul

Mon 10/13

5:15 am-6:45 am

Nonstop1h 30m

$130

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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 September 16, 2025.

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 $97, Southwest 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 cheapest airlines to fly from Chicago Midway Airport to Wisconsin one-way?

    To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $49. Southwest flights start at $49 while deals on Frontier start at $100 one-way.

  • 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.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Wisconsin?

    Currently, February is the cheapest month in which you can book a flight from Chicago Midway Airport to Wisconsin (average of $280). Flying from Chicago Midway Airport to Wisconsin in June is currently the most expensive (average of $376). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 Seattle flights
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