HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$59+ Cheap flights from Wisconsin to Midway (MDW)

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 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MDW
Oct 8 — Oct 151
Wed 10/8
Wed 10/15
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Wisconsin to Midway 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 Wisconsin to Midway

Keep the following information in mind while searching for Wisconsin to Midway flight deals. Data was last updated September 8, 2025.

Round-trip from

$117
(Southwest)

One-way from

$59
(Delta)

Popular in

November

Cheapest in

June

Average price

$239
From Wisconsin to Chicago Midway
Search Deals
One-way flight from Wisconsin to Chicago Midway
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($56 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find flight deals from Wisconsin to Midway

Cheapest flights from Wisconsin to Midway
Explore the most affordable flight options available from Wisconsin to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 8, 2025.

This Southwest deal was found by Cheapflights users on 9/5. 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 12/2412:25 pmMSP - MDW
Nonstop1h 30mSouthwest
Thu 1/11:45 pmMDW - MSP
Nonstop1h 30mSouthwest
Deal found 9/5$97
This Delta deal was found by Cheapflights users on 9/7. 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 10/284:08 pmMSP - MDW
Nonstop1h 35mDelta
Wed 10/299:20 amMDW - MSP
Nonstop1h 42mDelta
Deal found 9/7$117
This Delta deal was found by Cheapflights users on 9/6. 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.
Sun 10/57:14 amMSP - MDW
Nonstop1h 39mDelta
Wed 10/81:48 pmMDW - MSP
Nonstop1h 40mDelta
Deal found 9/6$120
This Delta deal was found by Cheapflights users on 9/6. 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.
Sat 10/47:14 amMSP - MDW
Nonstop1h 39mDelta
Tue 10/79:20 amMDW - MSP
Nonstop1h 42mDelta
Deal found 9/6$127
This Southwest deal was found by Cheapflights users on 9/7. 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 11/25:45 amMSP - MDW
Nonstop1h 45mSouthwest
Tue 11/41:45 pmMDW - MSP
Nonstop1h 30mSouthwest
Deal found 9/7$130
This Delta deal was found by Cheapflights users on 9/7. 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 10/237:15 amMSP - MDW
Nonstop1h 40mDelta
Mon 10/279:20 amMDW - MSP
Nonstop1h 42mDelta
Deal found 9/7$137
This Southwest deal was found by Cheapflights users on 9/7. 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 12/45:35 pmMSP - MDW
Nonstop1h 40mSouthwest
Sun 12/77:55 amMDW - MSP
Nonstop1h 30mSouthwest
Deal found 9/7$140
This Southwest deal was found by Cheapflights users on 9/5. 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.
Sun 9/285:05 amMSP - MDW
Nonstop1h 25mSouthwest
Mon 9/298:40 pmMDW - MSP
Nonstop1h 35mSouthwest
Deal found 9/5$141
This Southwest deal was found by Cheapflights users on 9/8. 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 10/246:55 pmMSP - MDW
Nonstop1h 30mSouthwest
Sun 10/267:55 amMDW - MSP
Nonstop1h 30mSouthwest
Deal found 9/8$143
This Frontier deal was found by Cheapflights users on 9/8. 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.
Thu 9/2512:25 pmMSP - MDW
1 stop10h 55mFrontier
Mon 9/294:48 pmMDW - MSP
1 stop7h 28mFrontier
Deal found 9/8$144
This Frontier deal was found by Cheapflights users on 9/7. 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.
Thu 10/236:00 amMSP - MDW
1 stop18h 36mFrontier
Mon 10/2712:11 pmMDW - MSP
1 stop11h 42mFrontier
Deal found 9/7$145
This Delta deal was found by Cheapflights users on 9/6. 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.
Sat 10/1112:05 pmATW - MDW
1 stop5h 38mDelta
Tue 10/149:20 amMDW - ATW
1 stop6h 17mDelta
Deal found 9/6$199

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin to Midway 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 8, 2025.
Use the filters below to find and compare flights from Wisconsin to Chicago Midway Airport that are best for you.

Fly from

Wisconsin

Fly to

Midway

Route

Depart

Return

Price

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 12/24

12:25 pm-1:55 pm

Nonstop1h 30m

Chicago Midway

Thu 1/1

1:45 pm-3:15 pm

Nonstop1h 30m

$97

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 10/28

4:08 pm-5:43 pm

Nonstop1h 35m

Chicago Midway

Wed 10/29

9:20 am-11:02 am

Nonstop1h 42m

$117

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 11/12

7:15 am-9:00 am

Nonstop1h 45m

Chicago Midway

Wed 11/12

1:45 pm-3:15 pm

Nonstop1h 30m

$117

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 10/7

7:45 am-9:15 am

Nonstop1h 30m

Chicago Midway

Tue 10/14

11:10 am-12:40 pm

Nonstop1h 30m

$117

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sun 10/5

7:14 am-8:53 am

Nonstop1h 39m

Chicago Midway

Wed 10/8

1:48 pm-3:28 pm

Nonstop1h 40m

$120

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sun 11/2

5:45 am-7:30 am

Nonstop1h 45m

Chicago Midway

Tue 11/4

1:45 pm-3:15 pm

Nonstop1h 30m

$120

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 10/11

4:08 pm-5:43 pm

Nonstop1h 35m

Chicago Midway

Tue 10/14

9:20 am-11:02 am

Nonstop1h 42m

$127

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 10/4

7:14 am-8:53 am

Nonstop1h 39m

Chicago Midway

Tue 10/7

9:20 am-11:02 am

Nonstop1h 42m

$127

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 10/23

7:15 am-8:55 am

Nonstop1h 40m

Chicago Midway

Tue 10/28

1:48 pm-3:28 pm

Nonstop1h 40m

$127

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

Sat 10/11

12:05 pm-5:43 pm

1 stop5h 38m

Chicago Midway

Tue 10/14

9:20 am-3:37 pm

1 stop6h 17m

$199

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/5

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Wisconsin to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Wisconsin 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 Wisconsin to Chicago Midway Airport
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 Wisconsin to Midway. 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 Wisconsin to Chicago Midway Airport?

    A quick flight from Wisconsin to Chicago Midway Airport can take about 1h 30m. Southwest provides one of the quickest options available for as low as $97. The distance between Wisconsin and Chicago Midway Airport is about 348 mi. All flights are typically nonstop.

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

    One-way options have recently been found by users for as low as $59 on Southwest. Other airlines that offer cheap prices include Delta from $59 and Frontier from $210 one-way.

  • What are the most popular routes from Wisconsin to Chicago Midway Airport?

    While some choose either Duluth Intl - Chicago Midway or Appleton Intl - Chicago Midway, Minneapolis St Paul - Chicago Midway is the most popular route from Wisconsin to Chicago Midway Airport.

  • Can I find deals for flights from Wisconsin to Midway that include hotel bookings?

    Yes. In addition to deals on Wisconsin to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Wisconsin to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Wisconsin to Midway.

  • Can I find deals for business class flights from Wisconsin to Midway?

    Yes. Cheapflights offers flight deals from Wisconsin to Midway 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 Wisconsin to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Wisconsin to Chicago Midway Airport (average of $160). Flying from Wisconsin to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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 Wisconsin to Midway

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Newark to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Seattle to O'Hare Intl flights
Atlanta to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Boston to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Denver to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Ontario to O'Hare Intl flights
Newark to Midway flights
Baltimore to Midway flights
Hobby to Midway flights
Atlanta to Midway flights
LaGuardia to Midway flights
Santa Ana to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Los Angeles to Midway flights
Dulles Intl to Midway flights
Austin to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Philadelphia to Midway flights
Hobby to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Burbank to O'Hare Intl flights
Portland to O'Hare Intl flights
Denver to Midway flights
George Bush Intcntl to O'Hare Intl flights
Minneapolis to Midway flights
Orlando to O'Hare Intl flights
Seattle to Midway flights
San Diego to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
George Bush Intcntl to Midway flights
Fort Lauderdale to O'Hare Intl flights
Tampa to O'Hare Intl flights
Orlando to Midway flights
Reagan-National to Midway flights
San Francisco to Midway flights
San Jose to O'Hare Intl flights
Hartford to O'Hare Intl flights
Sky Harbor Intl to Midway flights
Salt Lake City to O'Hare Intl 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.