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Midway

$72+ 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 8/6. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MDW
Aug 7 — Aug 141
Fri 8/7
Fri 8/14
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 July 8, 2026.

This Southwest deal was found by Cheapflights users on 7/7. 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 8/65:45 am
MKE
-
MDW
Nonstop0h 45m
Southwest
Mon 8/1010:10 am
MDW
-
MKE
Nonstop0h 50m
Southwest
Deal found 7/7$143
This Southwest deal was found by Cheapflights users on 7/7. 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.
Tue 8/46:40 am
MKE
-
MDW
Nonstop0h 50m
Southwest
Tue 8/112:00 pm
MDW
-
MKE
1 stop5h 55m
Southwest
Deal found 7/7$154
This Delta deal was found by Cheapflights users on 7/7. 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.
Sat 8/226:57 am
MSP
-
MDW
Nonstop1h 42m
Delta
Thu 8/279:59 am
MDW
-
MSP
Nonstop1h 43m
Delta
Deal found 7/7$177
This Southwest deal was found by Cheapflights users on 7/7. 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.
Tue 9/15:35 pm
MSP
-
MDW
Nonstop1h 30m
Southwest
Wed 9/28:30 pm
MDW
-
MSP
Nonstop1h 30m
Southwest
Deal found 7/7$178
This Southwest deal was found by Cheapflights users on 7/3. 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 8/67:40 am
MSP
-
MDW
Nonstop1h 30m
Southwest
Mon 8/108:00 am
MDW
-
MSP
Nonstop1h 45m
Southwest
Deal found 7/3$181
This Southwest deal was found by Cheapflights users on 7/7. 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.
Wed 8/54:30 pm
MSP
-
MDW
1 stop5h 20m
Southwest
Thu 8/68:00 am
MDW
-
MSP
Nonstop1h 45m
Southwest
Deal found 7/7$187
This Southwest deal was found by Cheapflights users on 7/7. 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.
Tue 8/115:35 pm
MSP
-
MDW
Nonstop1h 30m
Southwest
Sat 8/158:00 am
MDW
-
MSP
Nonstop1h 45m
Southwest
Deal found 7/7$190
This Southwest deal was found by Cheapflights users on 7/7. 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.
Sat 8/297:05 am
MSP
-
MDW
2 stops9h 50m
Southwest
Tue 9/15:10 pm
MDW
-
MSP
Nonstop1h 30m
Southwest
Deal found 7/7$192
This Southwest deal was found by Cheapflights users on 7/7. 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 8/67:55 am
MSP
-
MDW
1 stop7h 30m
Southwest
Sat 8/88:00 am
MDW
-
MSP
Nonstop1h 45m
Southwest
Deal found 7/7$193
This Delta deal was found by Cheapflights users on 7/7. 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 8/256:57 am
MSP
-
MDW
Nonstop1h 42m
Delta
Tue 8/257:25 pm
MDW
-
MSP
Nonstop1h 45m
Delta
Deal found 7/7$195
This Southwest deal was found by Cheapflights users on 7/3. 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 8/173:45 pm
MSP
-
MDW
Nonstop1h 30m
Southwest
Mon 8/248:15 am
MDW
-
MSP
2 stops6h 45m
Southwest
Deal found 7/3$196
This Southwest deal was found by Cheapflights users on 7/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:45 am
MKE
-
MDW
Nonstop0h 45m
Southwest
Sun 8/1610:25 am
MDW
-
MKE
Nonstop0h 45m
Southwest
Deal found 7/6$209

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 July 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$143
(Southwest)

One-way from

$72
(Southwest)

Good round-trip deal

$346 or less

Good one-way deal

$168 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
Price to beat on a round-trip flight from Wisconsin to Chicago Midway.
Search Deals
Price to beat on a one-way 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 July 8, 2026.
Use the filters below to find and compare flights from Wisconsin to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Tue 8/4

6:40 am-7:30 am

Nonstop0h 50m

Chicago Midway

Tue 8/11

10:15 am-11:05 am

Nonstop0h 50m

$144

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Thu 8/6

5:40 pm-10:20 pm

1 stop4h 40m

Chicago Midway

Mon 8/10

8:40 pm-9:25 pm

Nonstop0h 45m

$171

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Mon 8/17

7:55 am-12:15 pm

1 stop4h 20m

Chicago Midway

Mon 8/24

10:00 am-11:30 am

Nonstop1h 30m

$191

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 8/20

6:20 pm-7:50 pm

Nonstop1h 30m

Chicago Midway

Mon 8/24

5:50 pm-10:25 pm

1 stop4h 35m

$191

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 8/27

2:45 pm-10:00 pm

1 stop7h 15m

Chicago Midway

Mon 8/31

8:40 pm-10:10 pm

Nonstop1h 30m

$211

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Wed 8/12

3:40 pm-4:30 pm

Nonstop0h 50m

Chicago Midway

Wed 8/19

10:15 am-11:05 am

Nonstop0h 50m

$219

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Thu 7/30

5:15 pm-6:05 pm

Nonstop0h 50m

Chicago Midway

Sun 8/2

10:25 pm-11:15 pm

Nonstop0h 50m

$219

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Sat 7/25

5:45 am-6:35 am

Nonstop0h 50m

Chicago Midway

Sun 7/26

10:25 pm-11:15 pm

Nonstop0h 50m

$219

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Fri 7/31

5:50 pm-11:05 pm

1 stop5h 15m

Chicago Midway

Fri 8/7

8:40 pm-9:25 pm

Nonstop0h 45m

$229

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Fri 10/2

5:35 pm-11:05 pm

1 stop5h 30m

Chicago Midway

Mon 10/5

7:45 am-9:10 am

Nonstop1h 25m

$240

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/7

Showing 1-10 of 60 resultsSorted by cheapest first
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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

What is the cheapest time of day to fly from WI to MDW?

Find hourly flight availability from Wisconsin to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 8, 2026.

When flying from Wisconsin to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 45m. Southwest provides one of the quickest options available for as low as $143. The distance between Wisconsin and Chicago Midway Airport is about 80 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 $129. While the most popular route (Minneapolis St Paul - Chicago Midway) can be booked for $177 on average, our data indicates $327 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
Benton Harbor
Hammond
Lansing
Merrillville
Valparaiso
Porter

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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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