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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 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MKE
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$107
(Southwest)

One-way from

$59
(Southwest)

Popular in

December

Cheapest in

April

Average price

$272
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. 25% potential increase in price ($96 potential increase over avg. RT price).
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Cheapest flight prices on average. 10% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This Southwest deal was found by Cheapflights users on 7/2. 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 8/185:25 pmMDW - MSP
Nonstop1h 35mSouthwest
Thu 8/212:20 pmMSP - MDW
1 stop3h 10mSouthwest
Deal found 7/2$107
This Delta deal was found by Cheapflights users on 7/3. 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 8/209:15 amMDW - MSP
Nonstop1h 38mDelta
Sat 9/204:00 pmMSP - MDW
Nonstop1h 35mDelta
Deal found 7/3$119
This Priceline deal was found by Cheapflights users on 7/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/77:40 amMDW - MSP
1 stop7h 49mFrontier
Mon 8/116:00 amMSP - MDW
1 stop5h 41mFrontier
Deal found 7/1$121
This Delta deal was found by Cheapflights users on 7/1. 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.
Sat 10/259:20 amMDW - DLH
1 stop6h 01mDelta
Tue 10/2812:00 pmDLH - MDW
1 stop6h 07mDelta
Deal found 7/1$198
This Delta deal was found by Cheapflights users on 7/2. 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.
Sat 8/166:17 pmMDW - GRB
1 stop4h 17mDelta
Sat 8/236:20 amGRB - MDW
1 stop6h 43mDelta
Deal found 7/2$199
This Delta deal was found by Cheapflights users on 7/2. 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.
Sat 8/169:15 amMDW - CWA
1 stop6h 28mDelta
Sat 8/237:00 amCWA - MDW
1 stop6h 03mDelta
Deal found 7/2$321
This Delta deal was found by Cheapflights users on 7/1. 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.
Sat 8/239:15 amMDW - RHI
1 stop12h 07mDelta
Mon 8/256:30 amRHI - MDW
1 stop11h 07mDelta
Deal found 7/1$428
This Delta deal was found by Cheapflights users on 7/2. 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 7/186:20 pmMDW - MSN
1 stop14h 27mDelta
Mon 7/217:00 amMSN - MDW
1 stop11h 40mDelta
Deal found 7/2$815
This Delta deal was found by Cheapflights users on 7/2. 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.
Sat 7/269:25 amMDW - MKE
1 stop6h 38mDelta
Mon 7/281:15 pmMKE - MDW
1 stop5h 25mDelta
Deal found 7/2$848

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 July 3, 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

Mon 8/18

5:25 pm-7:00 pm

Nonstop1h 35m

Minneapolis St Paul

Thu 8/21

2:20 pm-5:30 pm

1 stop3h 10m

$107

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Wed 8/20

9:15 am-10:53 am

Nonstop1h 38m

Minneapolis St Paul

Sat 9/20

4:00 pm-5:35 pm

Nonstop1h 35m

$119

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Thu 8/7

7:40 am-3:29 pm

1 stop7h 49m

Minneapolis St Paul

Mon 8/11

6:00 am-11:41 am

1 stop5h 41m

$121

ChicagoGreen Bay

MDW - GRB

MDWGRB

Chicago Midway

Sat 8/16

6:17 pm-10:34 pm

1 stop4h 17m

Green Bay Austin-Straubel

Sat 8/23

6:20 am-1:03 pm

1 stop6h 43m

$199

ChicagoDuluth

MDW - DLH

MDWDLH

Chicago Midway

Sat 8/9

7:21 pm-10:44 pm

1 stop3h 23m

Duluth Intl

Sat 8/16

7:50 am-1:03 pm

1 stop5h 13m

$288

ChicagoWausau

MDW - CWA

MDWCWA

Chicago Midway

Sat 8/16

9:15 am-3:43 pm

1 stop6h 28m

Wausau Central Wisconsin

Sat 8/23

7:00 am-1:03 pm

1 stop6h 03m

$321

ChicagoRhinelander

MDW - RHI

MDWRHI

Chicago Midway

Sat 8/23

9:15 am-9:22 pm

1 stop12h 07m

Rhinelander Oneida County

Mon 8/25

6:30 am-5:37 pm

1 stop11h 07m

$428

ChicagoMadison

MDW - MSN

MDWMSN

Chicago Midway

Fri 7/18

6:20 pm-8:47 am

1 stop14h 27m

Madison Truax Field

Mon 7/21

7:00 am-6:40 pm

1 stop11h 40m

$815

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Sat 7/26

9:25 am-4:03 pm

1 stop6h 38m

Milwaukee-Mitchell

Mon 7/28

1:15 pm-6:40 pm

1 stop5h 25m

$848

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Wed 8/20

5:40 pm-10:25 pm

1 stop4h 45m

$59

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 20 results
1
2

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 July 3, 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.

Reviews of airlines servicing Wisconsin

Get insights into the airlines that provide service to Wisconsin. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Wisconsin. Reviews last updated July 3, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Wisconsin, such as Southwest, Delta, and Frontier. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,286 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Wisconsin one-way?

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $59. Frontier flights start at $62 while deals on Delta start at $71 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 - 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.

  • 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.

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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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