HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$49+ 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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MDW
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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.

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 October 30, 2025.

This Delta deal was found by Cheapflights users on 10/28. 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 12/107:24 amMSP - MDW
Nonstop1h 55mDelta
Wed 12/107:02 pmMDW - MSP
Nonstop1h 43mDelta
Deal found 10/28$97
This Southwest deal was found by Cheapflights users on 10/29. 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 12/85:30 amMSP - MDW
1 stop5h 55mSouthwest
Tue 12/911:25 amMDW - MSP
Nonstop1h 30mSouthwest
Deal found 10/29$107
This Frontier deal was found by Cheapflights users on 10/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1011:30 amMSP - MDW
1 stop7h 09mFrontier
Mon 11/1712:30 pmMDW - MSP
1 stop11h 44mFrontier
Deal found 10/27$110
This Southwest deal was found by Cheapflights users on 10/28. 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 12/103:50 pmMSP - MDW
1 stop4h 55mSouthwest
Mon 12/155:15 pmMDW - MSP
1 stop4h 30mSouthwest
Deal found 10/28$117
This Delta deal was found by Cheapflights users on 10/30. 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 12/54:30 pmMSP - MDW
Nonstop1h 48mDelta
Mon 12/87:02 pmMDW - MSP
Nonstop1h 43mDelta
Deal found 10/30$120
This Southwest deal was found by Cheapflights users on 10/29. 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 12/55:35 pmMSP - MDW
Nonstop1h 40mSouthwest
Mon 12/85:15 pmMDW - MSP
1 stop4h 30mSouthwest
Deal found 10/29$130
This Southwest deal was found by Cheapflights users on 10/29. 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 12/35:45 amMSP - MDW
2 stops6h 45mSouthwest
Sun 12/77:55 amMDW - MSP
Nonstop1h 30mSouthwest
Deal found 10/29$135
This Delta deal was found by Cheapflights users on 10/28. 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 12/57:24 amMSP - MDW
Nonstop1h 55mDelta
Sun 12/71:50 pmMDW - MSP
Nonstop1h 40mDelta
Deal found 10/28$143
This Delta deal was found by Cheapflights users on 10/28. 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 12/65:00 amDLH - MDW
1 stop4h 19mDelta
Wed 12/107:02 pmMDW - DLH
1 stop4h 57mDelta
Deal found 10/28$198
This Delta deal was found by Cheapflights users on 10/29. 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 11/237:00 amATW - MDW
1 stop5h 34mDelta
Thu 11/279:41 amMDW - ATW
1 stop5h 57mDelta
Deal found 10/29$199
This Delta deal was found by Cheapflights users on 10/30. 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 12/65:00 amDLH - MDW
2 stops7h 34mDelta
Mon 12/87:02 pmMDW - DLH
1 stop4h 57mDelta
Deal found 10/30$219
This Delta deal was found by Cheapflights users on 10/29. 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 11/257:00 amATW - MDW
1 stop5h 34mDelta
Thu 11/279:41 amMDW - ATW
1 stop5h 57mDelta
Deal found 10/29$229

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$97
(Delta)

One-way from

$49
(Delta)

Popular in

November

Cheapest in

June

Average price

$222
Provider with most accurate pricing for Milwaukee-Mitchell-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Chicago (CHI) flights.
Search Deals
From Wisconsin to Chicago Midway
Search Deals
One-way flight from Wisconsin to Chicago Midway
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($41 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 30, 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 12/10

7:24 am-9:19 am

Nonstop1h 55m

Chicago Midway

Wed 12/10

1:50 pm-3:30 pm

Nonstop1h 40m

$97

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 12/17

5:45 am-12:35 pm

2 stops6h 50m

Chicago Midway

Wed 12/31

8:45 pm-10:15 pm

Nonstop1h 30m

$112

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 12/3

4:30 pm-6:18 pm

Nonstop1h 48m

Chicago Midway

Fri 12/5

1:50 pm-3:30 pm

Nonstop1h 40m

$120

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Fri 12/12

7:24 am-9:19 am

Nonstop1h 55m

Chicago Midway

Mon 12/15

9:59 am-11:42 am

Nonstop1h 43m

$120

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Fri 12/5

7:15 am-9:00 am

Nonstop1h 45m

Chicago Midway

Mon 12/8

5:15 pm-9:45 pm

1 stop4h 30m

$130

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 12/30

9:10 am-11:06 am

Nonstop1h 56m

Chicago Midway

Wed 12/31

11:48 am-1:32 pm

Nonstop1h 44m

$157

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 11/18

4:40 pm-6:18 pm

Nonstop1h 38m

Chicago Midway

Wed 11/19

9:41 am-11:23 am

Nonstop1h 42m

$163

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 12/4

6:10 am-12:34 pm

1 stop6h 24m

Chicago Midway

Sun 12/7

7:02 pm-8:45 pm

Nonstop1h 43m

$190

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 12/9

8:50 am-12:34 pm

1 stop3h 44m

Chicago Midway

Fri 12/12

1:50 pm-3:30 pm

Nonstop1h 40m

$190

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Sat 12/6

5:00 am-9:19 am

1 stop4h 19m

Chicago Midway

Wed 12/10

7:02 pm-11:59 pm

1 stop4h 57m

$198

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

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 55m. Delta provides one of the quickest options available for as low as $97. The distance between Wisconsin and Chicago Midway Airport is about 348 mi. This flight may include one or multiple stops.

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

    While some choose either Milwaukee-Mitchell - Chicago Midway or Duluth 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.

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
Porter
Benton Harbor

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
Dallas/Fort Worth to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Newark to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Seattle to O'Hare Intl flights
Denver to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Boston to O'Hare Intl flights
Atlanta to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Baltimore to Midway flights
Dallas/Fort Worth to Midway flights
Ontario to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Los Angeles to Midway flights
Hobby to Midway flights
Atlanta to Midway flights
LaGuardia to Midway flights
Newark to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Denver to Midway flights
Philadelphia to Midway flights
Charlotte to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
San Francisco to Midway flights
George Bush Intcntl to O'Hare Intl flights
Dulles Intl to Midway flights
Hobby to O'Hare Intl flights
Tampa to O'Hare Intl flights
Miami to O'Hare Intl flights
Minneapolis to Midway flights
Raleigh to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Reagan-National to Midway flights
Austin to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Love Field to O'Hare Intl flights
Hartford to O'Hare Intl flights
Orlando to O'Hare Intl flights
San Diego to O'Hare Intl flights
Portland to O'Hare Intl flights
Boston to Midway flights
Providence to O'Hare Intl flights
Sacramento to O'Hare Intl flights
Columbus 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.