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$67+ 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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MDW
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This Delta deal was found by Cheapflights users on 12/16. 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 12/249:10 amMSP - MDW
Nonstop1h 56mDelta
Thu 12/2511:48 amMDW - MSP
Nonstop1h 44mDelta
Deal found 12/16$178
This Southwest deal was found by Cheapflights users on 12/17. 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 12/315:30 amMSP - MDW
1 stop5h 55mSouthwest
Thu 1/11:45 pmMDW - MSP
Nonstop1h 30mSouthwest
Deal found 12/17$240
This Trip.com deal was found by Cheapflights users on 12/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/208:42 pmMSP - MDW
1 stop25h 08mFrontier
Sun 1/410:50 pmMDW - MSP
1 stop25h 12mFrontier
Deal found 12/17$242
This Delta deal was found by Cheapflights users on 12/16. 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 12/253:30 pmMSP - MDW
Nonstop1h 49mDelta
Mon 12/295:59 pmMDW - MSP
Nonstop1h 46mDelta
Deal found 12/16$304
This Delta deal was found by Cheapflights users on 12/16. 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 12/253:30 pmMSP - MDW
Nonstop1h 49mDelta
Wed 12/3111:48 amMDW - MSP
Nonstop1h 44mDelta
Deal found 12/16$310
This Southwest deal was found by Cheapflights users on 12/15. 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 12/235:00 amMSP - MDW
Nonstop1h 45mSouthwest
Tue 1/61:50 pmMDW - MSP
1 stop8h 00mSouthwest
Deal found 12/15$315
This Delta deal was found by Cheapflights users on 12/15. 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 12/239:10 amMSP - MDW
Nonstop1h 56mDelta
Tue 1/67:16 pmMDW - MSP
Nonstop1h 44mDelta
Deal found 12/15$318
This Delta deal was found by Cheapflights users on 12/15. 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 12/319:10 amMSP - MDW
Nonstop1h 56mDelta
Tue 1/67:16 pmMDW - MSP
Nonstop1h 44mDelta
Deal found 12/15$319
This Delta deal was found by Cheapflights users on 12/15. 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 12/197:00 amATW - MDW
1 stop5h 34mDelta
Tue 12/305:59 pmMDW - ATW
1 stop5h 10mDelta
Deal found 12/15$338
This Delta deal was found by Cheapflights users on 12/16. 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 12/2311:00 amATW - MDW
1 stop6h 26mDelta
Tue 12/305:59 pmMDW - ATW
1 stop5h 10mDelta
Deal found 12/16$341
This Southwest deal was found by Cheapflights users on 12/15. 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 12/195:50 amMKE - MDW
1 stop4h 15mSouthwest
Wed 12/318:25 amMDW - MKE
1 stop3h 15mSouthwest
Deal found 12/15$348
This Southwest deal was found by Cheapflights users on 12/15. 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 12/246:00 amMKE - MDW
1 stop5h 25mSouthwest
Mon 1/56:45 amMDW - MKE
1 stop4h 20mSouthwest
Deal found 12/15$353

Find flight deals from Wisconsin to Midway

Keep the following information in mind while searching for Wisconsin to Midway flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$133
(Delta)

One-way from

$67
(Southwest)

Popular in

January

Cheapest in

June

Average price

$179

Good round-trip deal

$383 or less
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. 19% potential increase in price ($68 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($30 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Wisconsin to Chicago Midway.
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 December 18, 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 1/14

4:50 pm-6:32 pm

Nonstop1h 42m

Chicago Midway

Wed 1/21

9:50 am-11:34 am

Nonstop1h 44m

$133

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 1/13

2:30 pm-9:50 pm

1 stop7h 20m

Chicago Midway

Tue 1/20

8:40 am-10:20 am

Nonstop1h 40m

$143

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 1/24

9:10 am-11:05 am

Nonstop1h 55m

Chicago Midway

Tue 1/27

1:49 pm-3:37 pm

Nonstop1h 48m

$152

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 2/24

11:22 am-1:07 pm

Nonstop1h 45m

Chicago Midway

Thu 2/26

9:50 am-11:32 am

Nonstop1h 42m

$152

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 1/22

7:05 am-9:08 am

Nonstop2h 03m

Chicago Midway

Mon 1/26

9:50 am-11:34 am

Nonstop1h 44m

$171

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 1/24

2:30 pm-4:16 pm

Nonstop1h 46m

Chicago Midway

Mon 1/26

1:49 pm-3:37 pm

Nonstop1h 48m

$171

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 1/22

7:05 am-9:08 am

Nonstop2h 03m

Chicago Midway

Thu 1/22

1:49 pm-3:37 pm

Nonstop1h 48m

$171

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 1/24

6:15 am-11:35 am

1 stop5h 20m

Chicago Midway

Tue 1/27

1:25 pm-8:35 pm

2 stops7h 10m

$177

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 1/22

7:20 am-9:15 am

Nonstop1h 55m

Chicago Midway

Thu 1/22

1:25 pm-8:35 pm

2 stops7h 10m

$186

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 1/15

7:00 am-8:50 am

Nonstop1h 50m

Chicago Midway

Mon 1/19

12:30 pm-10:20 pm

1 stop9h 50m

$187

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 60 results
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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 42m. Delta provides one of the quickest options available for as low as $133. 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 Madison Truax Field - Chicago Midway or Duluth Intl - Chicago Midway, Minneapolis St Paul - Chicago Midway is the most popular route from Wisconsin to Chicago Midway Airport.

  • What are the cheapest flights from Wisconsin to Chicago Midway Airport?

    Looking at all options, your cheapest flight can be booked for $328. While the most popular route (Minneapolis St Paul - Chicago Midway) can be booked for $133 on average, our data indicates $416 when flying 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Wisconsin to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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