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Midway

$63+ 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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MDW
jul. 8 — jul. 151
mar. 7/8
mar. 7/15
1 adult, Economy
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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 julio 3, 2025.

Round-trip from

$117
(Southwest)

One-way from

$63
(Priceline)

Popular in

November

Cheapest in

March
From Wisconsin to Chicago Midway
Search Deals
One-way flight from Wisconsin to Chicago Midway
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($18 potential savings vs. average RT price).
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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 julio 3, 2025.

This Southwest deal was found by Cheapflights users on 7/2. 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.
mar. 8/194:30 pmMSP - MDW
1 stop5h 25mSouthwest
mié. 8/205:40 pmMDW - MSP
1 stop4h 45mSouthwest
Deal found 7/2$117
This Delta deal was found by Cheapflights users on 7/1. 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.
sáb. 10/184:30 pmMSP - MDW
Nonstop1h 37mDelta
mar. 10/219:20 amMDW - MSP
Nonstop1h 39mDelta
Deal found 7/1$119
This Priceline deal was found by Cheapflights users on 7/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/126:45 amMSP - MDW
1 stop9h 08mFrontier
lun. 9/154:48 pmMDW - MSP
1 stop7h 28mFrontier
Deal found 7/2$161
This Delta deal was found by Cheapflights users on 6/30. 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.
mié. 7/211:59 amATW - MDW
1 stop5h 41mDelta
mié. 8/61:09 pmMDW - ATW
1 stop4h 18mDelta
Deal found 6/30$293
This Delta deal was found by Cheapflights users on 7/2. 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.
jue. 8/77:00 amGRB - MDW
1 stop5h 29mDelta
sáb. 8/166:17 pmMDW - GRB
1 stop4h 17mDelta
Deal found 7/2$349
This Delta deal was found by Cheapflights users on 7/2. 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.
vie. 7/42:00 pmDLH - MDW
1 stop3h 40mDelta
dom. 7/67:21 pmMDW - DLH
1 stop4h 19mDelta
Deal found 7/2$358
This Delta deal was found by Cheapflights users on 7/2. 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.
sáb. 8/27:05 amCWA - MDW
1 stop6h 01mDelta
dom. 8/39:25 amMDW - CWA
2 stops11h 36mDelta
Deal found 7/2$394
This Delta deal was found by Cheapflights users on 7/1. 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.
mié. 7/166:15 amESC - MDW
1 stop3h 29mDelta
dom. 7/206:20 pmMDW - ESC
1 stop3h 24mDelta
Deal found 7/1$417

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 julio 3, 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

mar. 8/19

4:30 pm-9:55 pm

1 stop5h 25m

Chicago Midway

mié. 8/20

5:40 pm-10:25 pm

1 stop4h 45m

$117

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

sáb. 10/18

7:00 am-8:46 am

Nonstop1h 46m

Chicago Midway

mar. 10/21

9:20 am-10:59 am

Nonstop1h 39m

$119

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

vie. 9/12

6:45 am-3:53 pm

1 stop9h 08m

Chicago Midway

lun. 9/15

4:48 pm-12:16 am

1 stop7h 28m

$161

Green BayChicago

GRB - MDW

GRBMDW

Green Bay Austin-Straubel

jue. 8/7

7:00 am-12:29 pm

1 stop5h 29m

Chicago Midway

sáb. 8/16

6:17 pm-10:34 pm

1 stop4h 17m

$349

WausauChicago

CWA - MDW

CWAMDW

Wausau Central Wisconsin

sáb. 8/2

7:05 am-1:06 pm

1 stop6h 01m

Chicago Midway

dom. 8/3

9:25 am-9:01 pm

2 stops11h 36m

$394

EscanabaChicago

ESC - MDW

ESCMDW

Escanaba Delta County Arpt

mié. 7/16

6:15 am-8:44 am

1 stop3h 29m

Chicago Midway

dom. 7/20

6:20 pm-10:44 pm

1 stop3h 24m

$417

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

mié. 7/16

7:00 am-12:29 pm

1 stop5h 29m

Chicago Midway

sáb. 7/19

1:09 pm-5:27 pm

1 stop4h 18m

$419

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

vie. 9/5

7:50 am-1:03 pm

1 stop5h 13m

Chicago Midway

dom. 9/7

7:17 pm-10:46 pm

1 stop3h 29m

$468

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

sáb. 10/11

2:23 pm-12:11 am

1 stop9h 48m

$63

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

jue. 10/30

3:25 pm-11:15 pm

1 stop7h 50m

$64

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 17 results
1
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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.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated julio 3, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and Frontier from Wisconsin to Chicago Midway Airport by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,286 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • 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 $63 on Frontier. Other airlines that offer cheap prices include Southwest from $64 and Delta from $71 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 Wisconsin?

Book flights to Wisconsin if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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Alternative routes for Wisconsin to Midway

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