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$79+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MDW
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This Southwest deal was found by Cheapflights users on 1/27. 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 3/114:20 pm
MSP
-
MDW
1 stop6h 30m
Southwest
Wed 3/185:30 pm
MDW
-
MSP
1 stop6h 00m
Southwest
Deal found 1/27$117
This Southwest deal was found by Cheapflights users on 1/29. 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.
Tue 3/108:45 am
MSP
-
MDW
2 stops7h 25m
Southwest
Tue 3/105:30 pm
MDW
-
MSP
1 stop6h 00m
Southwest
Deal found 1/29$122
This Southwest deal was found by Cheapflights users on 1/28. 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 2/256:05 am
MSP
-
MDW
2 stops7h 50m
Southwest
Wed 3/41:25 pm
MDW
-
MSP
2 stops7h 10m
Southwest
Deal found 1/28$127
This Southwest deal was found by Cheapflights users on 1/27. 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.
Tue 3/37:20 am
MSP
-
MDW
Nonstop1h 55m
Southwest
Thu 3/52:20 pm
MDW
-
MSP
Nonstop1h 30m
Southwest
Deal found 1/27$134
This Southwest deal was found by Cheapflights users on 1/27. 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 4/157:10 am
MSP
-
MDW
2 stops8h 35m
Southwest
Thu 4/169:30 pm
MDW
-
MSP
Nonstop1h 30m
Southwest
Deal found 1/27$149
This KAYAK deal was found by Cheapflights users on 1/28. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/247:05 am
MSP
-
MDW
Nonstop2h 01m
Delta
Wed 2/251:49 pm
MDW
-
MSP
Nonstop1h 46m
Delta
Deal found 1/28$155
This Southwest deal was found by Cheapflights users on 1/26. 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 4/157:10 am
MSP
-
MDW
2 stops8h 35m
Southwest
Sat 4/189:10 am
MDW
-
MSP
1 stop5h 00m
Southwest
Deal found 1/26$159
This Southwest deal was found by Cheapflights users on 1/28. 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.
Tue 3/36:50 am
MSP
-
MDW
1 stop6h 35m
Southwest
Wed 3/48:40 am
MDW
-
MSP
Nonstop1h 40m
Southwest
Deal found 1/28$167
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/199:58 am
MSP
-
MDW
1 stop11h 14m
Frontier
Thu 2/263:00 pm
MDW
-
MSP
1 stop28h 25m
Frontier
Deal found 1/26$170
This Delta deal was found by Cheapflights users on 1/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2412:12 pm
ATW
-
MDW
1 stop6h 28m
Delta
Tue 3/31:29 pm
MDW
-
ATW
1 stop4h 16m
Delta
Deal found 1/27$199
This Delta deal was found by Cheapflights users on 1/28. 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 3/146:30 am
ATW
-
MDW
1 stop6h 55m
Delta
Sat 3/219:30 am
MDW
-
ATW
1 stop6h 13m
Delta
Deal found 1/28$214
This Southwest deal was found by Cheapflights users on 1/26. 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 2/245:30 am
MKE
-
MDW
1 stop4h 00m
Southwest
Tue 3/310:05 am
MDW
-
MKE
1 stop6h 55m
Southwest
Deal found 1/26$219

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$117
(Southwest)

One-way from

$79
(Super.com)

Popular in

January

Cheapest in

June

Average price

$361

Good round-trip deal

$251 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. 9% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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

Tue 3/24

5:07 pm-6:40 pm

Nonstop1h 33m

Chicago Midway

Mon 3/30

9:30 am-11:07 am

Nonstop1h 37m

$134

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 3/3

4:35 pm-6:10 pm

Nonstop1h 35m

Chicago Midway

Thu 3/5

10:15 am-11:45 am

Nonstop1h 30m

$134

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Mon 3/23

5:07 pm-6:40 pm

Nonstop1h 33m

Chicago Midway

Wed 4/1

7:20 pm-9:00 pm

Nonstop1h 40m

$134

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 3/14

5:06 pm-6:40 pm

Nonstop1h 34m

Chicago Midway

Wed 3/18

9:30 am-11:07 am

Nonstop1h 37m

$144

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 4/15

3:15 pm-4:50 pm

Nonstop1h 35m

Chicago Midway

Sat 4/18

3:30 pm-10:35 pm

2 stops7h 05m

$149

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 3/11

4:20 pm-10:50 pm

1 stop6h 30m

Chicago Midway

Sat 3/14

7:40 am-9:10 am

Nonstop1h 30m

$154

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 3/17

6:00 am-12:29 pm

1 stop6h 29m

Chicago Midway

Tue 3/17

7:20 pm-9:00 pm

Nonstop1h 40m

$167

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 2/19

4:59 pm-6:40 pm

Nonstop1h 41m

Chicago Midway

Mon 2/23

1:49 pm-3:35 pm

Nonstop1h 46m

$171

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 4/11

7:00 am-8:50 am

Nonstop1h 50m

Chicago Midway

Mon 4/13

2:12 pm-3:55 pm

Nonstop1h 43m

$171

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Mon 3/16

11:49 am-1:25 pm

Nonstop1h 36m

Chicago Midway

Fri 3/20

2:05 pm-3:44 pm

Nonstop1h 39m

$181

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

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 33m. Delta provides one of the quickest options available for as low as $134. The distance between Wisconsin and Chicago Midway Airport is about 348 mi. All flights are typically nonstop.

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

    While some choose either Duluth Intl - Chicago Midway or Milwaukee-Mitchell - 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 $248. While the most popular route (Minneapolis St Paul - Chicago Midway) can be booked for $97 on average, our data indicates $404 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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LaGuardia to Midway flights
Reagan-National to Midway flights
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Sky Harbor Intl to Midway flights
Love Field to O'Hare Intl flights
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Sacramento to O'Hare Intl flights
Hobby to O'Hare Intl flights
Minneapolis to Midway flights
San Antonio to O'Hare Intl flights
Kansas City to O'Hare Intl flights
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