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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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MKE
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$107
(Southwest)

One-way from

$59
(Southwest)

Popular in

December

Cheapest in

April

Average price

$305
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 June 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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/12. 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 8/257:40 amMDW - MSP
Nonstop1h 30mSouthwest
Wed 8/276:00 amMSP - MDW
1 stop3h 50mSouthwest
Deal found 6/12$107
This Delta deal was found by Cheapflights users on 6/10. 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 9/207:00 amMSP - MDW
Nonstop1h 46mDelta
Deal found 6/10$124
This Delta deal was found by Cheapflights users on 6/11. 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 6/259:21 amMDW - GRB
1 stop6h 23mDelta
Sat 6/287:00 amGRB - MDW
1 stop5h 29mDelta
Deal found 6/11$209
This Frontier deal was found by Cheapflights users on 6/12. 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 6/1312:35 pmMDW - MSP
1 stop12h 09mFrontier
Sat 6/144:13 pmMSP - MDW
1 stop6h 15mFrontier
Deal found 6/12$228
This Delta deal was found by Cheapflights users on 6/11. 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 8/267:17 pmMDW - DLH
1 stop3h 29mDelta
Sun 8/315:10 amDLH - MDW
2 stops7h 18mDelta
Deal found 6/11$269
This Delta deal was found by Cheapflights users on 6/11. 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 7/269:24 amMDW - CWA
1 stop6h 04mDelta
Sat 8/27:05 amCWA - MDW
1 stop6h 01mDelta
Deal found 6/11$375
This Mytrip deal was found by Cheapflights users on 6/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/2510:31 amMDW - MKE
2 stops29h 11mMultiple Airlines
Sun 7/274:37 pmMKE - MDW
2 stops21h 27mMultiple Airlines
Deal found 6/9$490
This Delta deal was found by Cheapflights users on 6/9. 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 9/31:08 pmMDW - RHI
2 stops8h 14mDelta
Sat 9/610:59 amRHI - MDW
1 stop6h 38mDelta
Deal found 6/9$509

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 June 12, 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 8/25

7:40 am-9:10 am

Nonstop1h 30m

Minneapolis St Paul

Wed 8/27

6:00 am-9:50 am

1 stop3h 50m

$107

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Wed 8/20

9:15 am-10:53 am

Nonstop1h 38m

Minneapolis St Paul

Sat 9/20

7:00 am-8:46 am

Nonstop1h 46m

$124

ChicagoGreen Bay

MDW - GRB

MDWGRB

Chicago Midway

Wed 6/25

9:21 am-3:44 pm

1 stop6h 23m

Green Bay Austin-Straubel

Sat 6/28

7:00 am-12:29 pm

1 stop5h 29m

$209

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Sat 7/26

6:20 am-2:51 pm

1 stop8h 31m

Minneapolis St Paul

Sat 8/2

4:14 pm-10:35 pm

1 stop6h 21m

$248

ChicagoDuluth

MDW - DLH

MDWDLH

Chicago Midway

Tue 8/26

7:17 pm-10:46 pm

1 stop3h 29m

Duluth Intl

Sun 8/31

5:10 am-12:28 pm

2 stops7h 18m

$269

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Fri 7/25

12:50 pm-2:06 pm

1 stop25h 16m

Minneapolis St Paul

Fri 8/1

7:54 am-11:17 pm

1 stop15h 23m

$315

ChicagoWausau

MDW - CWA

MDWCWA

Chicago Midway

Sat 7/26

9:24 am-3:28 pm

1 stop6h 04m

Wausau Central Wisconsin

Sat 8/2

7:05 am-1:06 pm

1 stop6h 01m

$375

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Fri 7/25

10:31 am-3:42 pm

2 stops29h 11m

Milwaukee-Mitchell

Sun 7/27

4:37 pm-2:04 pm

2 stops21h 27m

$490

ChicagoRhinelander

MDW - RHI

MDWRHI

Chicago Midway

Wed 9/3

1:08 pm-9:22 pm

2 stops8h 14m

Rhinelander Oneida County

Sat 9/6

10:59 am-5:37 pm

1 stop6h 38m

$509

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Tue 8/5

5:40 pm-10:25 pm

1 stop4h 45m

$59

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

Showing 1-10 of 21 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 June 12, 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.

Rainfall in Wisconsin by month

Plan your trip to Wisconsin by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Wisconsin ranges from 1.4 - 4.0 inches per month. June is typically the wettest month, when rainfall can reach 4.0 in. January is typically the driest time to visit Wisconsin when rainfall is around 1.4 in.

Temperature in Wisconsin by month

Plan your trip to Wisconsin by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Wisconsin, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 21.2 F).

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 June 12, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Allegiant Air from Chicago to Wisconsin by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

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
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

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.
Allegiant Air
7.3
Good
725 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

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
6.0
Okay
3,295 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

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. Delta flights start at $76 while deals on Frontier start at $106 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.

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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