HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Wisconsin

$61+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MKE
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Wisconsin with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 December 28, 2025.

This Southwest deal was found by Cheapflights users on 12/26. 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.
Tue 12/307:55 amMDW - MKE
1 stop4h 00mSouthwest
Thu 1/16:00 amMKE - MDW
1 stop5h 25mSouthwest
Deal found 12/26$334
This Southwest deal was found by Cheapflights users on 12/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/307:55 amMDW - MKE
1 stop4h 00mSouthwest
Wed 12/316:00 amMKE - MDW
1 stop5h 25mSouthwest
Deal found 12/25$363
This Southwest deal was found by Cheapflights users on 12/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/294:20 pmMDW - MKE
1 stop6h 25mSouthwest
Wed 12/316:00 amMKE - MDW
1 stop5h 25mSouthwest
Deal found 12/25$393
This Expedia deal was found by Cheapflights users on 12/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/302:01 pmMDW - MSP
1 stop9h 52mFrontier
Thu 1/111:49 amMSP - MDW
1 stop5h 49mFrontier
Deal found 12/26$442
This Southwest deal was found by Cheapflights users on 12/26. 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.
Tue 12/307:55 amMDW - MKE
1 stop4h 00mSouthwest
Tue 12/306:30 pmMKE - MDW
1 stop3h 15mSouthwest
Deal found 12/26$452
This Southwest deal was found by Cheapflights users on 12/27. 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.
Sat 12/275:35 pmMDW - MKE
1 stop6h 50mSouthwest
Wed 12/316:00 amMKE - MDW
1 stop5h 25mSouthwest
Deal found 12/27$544
This Southwest deal was found by Cheapflights users on 12/26. 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 12/297:55 amMDW - MKE
1 stop4h 00mSouthwest
Mon 12/296:30 pmMKE - MDW
1 stop3h 15mSouthwest
Deal found 12/26$547
This Southwest deal was found by Cheapflights users on 12/27. 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.
Sun 12/285:50 pmMDW - MSP
Nonstop1h 30mSouthwest
Sat 1/38:10 pmMSP - MDW
1 stop3h 45mSouthwest
Deal found 12/27$561
This Southwest deal was found by Cheapflights users on 12/27. 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 12/315:15 pmMDW - MSP
1 stop4h 30mSouthwest
Sat 1/38:10 pmMSP - MDW
1 stop3h 45mSouthwest
Deal found 12/27$570
This Southwest deal was found by Cheapflights users on 12/26. 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.
Tue 12/303:10 pmMDW - MSP
Nonstop1h 30mSouthwest
Fri 1/25:00 amMSP - MDW
Nonstop1h 45mSouthwest
Deal found 12/26$594
This Southwest deal was found by Cheapflights users on 12/26. 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.
Wed 12/318:25 amMDW - MSP
1 stop3h 25mSouthwest
Mon 1/55:30 amMSP - MDW
2 stops10h 15mSouthwest
Deal found 12/26$619
This Delta deal was found by Cheapflights users on 12/26. 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.
Sun 12/285:59 pmMDW - MSP
Nonstop1h 46mDelta
Fri 1/29:10 amMSP - MDW
Nonstop1h 56mDelta
Deal found 12/26$624

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 December 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$132
(Southwest)

One-way from

$61
(Southwest)

Popular in

December

Cheapest in

November

Average price

$394
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. 7% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 28, 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

Sat 1/17

2:30 pm-4:00 pm

Nonstop1h 30m

Minneapolis St Paul

Sun 1/18

7:20 am-9:15 am

Nonstop1h 55m

$132

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Sat 1/17

5:00 pm-6:54 pm

Nonstop1h 54m

Minneapolis St Paul

Sun 1/18

4:50 pm-6:32 pm

Nonstop1h 42m

$144

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Thu 3/12

9:30 am-11:07 am

Nonstop1h 37m

Minneapolis St Paul

Thu 3/12

5:08 pm-6:40 pm

Nonstop1h 32m

$191

ChicagoGreen Bay

MDW - GRB

MDWGRB

Chicago Midway

Fri 1/16

1:28 pm-4:39 pm

1 stop3h 11m

Green Bay Austin-Straubel

Sun 1/18

11:15 am-5:34 pm

1 stop6h 19m

$199

ChicagoGreen Bay

MDW - GRB

MDWGRB

Chicago Midway

Sat 1/24

11:45 am-3:35 pm

1 stop3h 50m

Green Bay Austin-Straubel

Sat 1/31

7:00 am-12:46 pm

1 stop5h 46m

$199

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Sat 1/17

11:45 am-1:32 pm

Nonstop1h 47m

Minneapolis St Paul

Wed 1/21

6:00 am-12:49 pm

1 stop6h 49m

$202

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Fri 3/13

7:40 am-9:10 am

Nonstop1h 30m

Minneapolis St Paul

Mon 3/16

4:25 pm-5:55 pm

Nonstop1h 30m

$214

ChicagoGreen Bay

MDW - GRB

MDWGRB

Chicago Midway

Thu 1/15

9:50 am-3:38 pm

1 stop5h 48m

Green Bay Austin-Straubel

Sun 1/18

7:00 am-12:48 pm

1 stop5h 48m

$214

ChicagoMinneapolis

MDW - MSP

MDWMSP

Chicago Midway

Sun 1/18

8:40 am-10:20 am

Nonstop1h 40m

Minneapolis St Paul

Wed 1/21

3:45 pm-5:25 pm

Nonstop1h 40m

$227

ChicagoMilwaukee

MDW - MKE

MDWMKE

Chicago Midway

Tue 2/3

1:15 pm-5:00 pm

1 stop3h 45m

Milwaukee-Mitchell

Thu 2/5

5:25 am-10:20 am

1 stop4h 55m

$228

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/27

Showing 1-10 of 58 results
1
2
3
...
6

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 $132, 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 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 - Wausau Central Wisconsin 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Wisconsin

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Las Vegas flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Orlando flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Miami flights
O'Hare Intl to Tampa flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Newark flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Denver flights
O'Hare Intl to Seattle flights
Midway to Miami flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to Honolulu flights
Midway to Newark flights
Midway to John F Kennedy Intl flights
Midway to Fort Lauderdale flights
Midway to Las Vegas flights
O'Hare Intl to Atlanta flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to San Diego flights
O'Hare Intl to West Palm Beach flights
Midway to LaGuardia flights
O'Hare Intl to Palm Springs flights
O'Hare Intl to Salt Lake City flights
Midway to Los Angeles flights
O'Hare Intl to Sarasota flights
Midway to Orlando flights
O'Hare Intl to Key West flights
O'Hare Intl to Ontario flights
O'Hare Intl to New Orleans flights
Midway to Dallas/Fort Worth flights
O'Hare Intl to Boston flights
O'Hare Intl to Baltimore flights
Midway to Tampa flights
O'Hare Intl to Austin flights
O'Hare Intl to Kahului flights
O'Hare Intl to Charleston flights
Midway to Sky Harbor Intl flights
O'Hare Intl to Dulles Intl flights
O'Hare Intl to George Bush Intcntl flights
O'Hare Intl to Nashville flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to Love Field flights
O'Hare Intl to Hobby flights
O'Hare Intl to Reno flights
O'Hare Intl to Tucson flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.