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Cheap flights from Wisconsin to Chicago from $72

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Wisconsin to Chicago departing on 8/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Wisconsin to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
4:20 pm - 5:10 pm
MKE
-
MDW
0h 50mnonstop
Southwest Logo
8:40 pm - 9:25 pm
MDW
-
MKE
0h 45mnonstop
$143Southwest
Thu, Aug 6 - Mon, Aug 10
Southwest Logo
5:45 am - 6:30 am
MKE
-
MDW
0h 45mnonstop
Southwest Logo
10:10 am - 11:00 am
MDW
-
MKE
0h 50mnonstop
$144Southwest
Thu, Aug 6 - Mon, Aug 10
Southwest Logo
4:50 pm - 9:55 pm
MKE
-
MDW
5h 05m
1 stop
Southwest Logo
8:40 pm - 9:25 pm
MDW
-
MKE
0h 45mnonstop
$153Southwest
Thu, Aug 6 - Mon, Aug 10
Southwest Logo
6:40 am - 7:30 am
MKE
-
MDW
0h 50mnonstop
Southwest Logo
2:00 pm - 7:55 pm
MDW
-
MKE
5h 55m
1 stop
$154Southwest
Tue, Aug 4 - Tue, Aug 11
Southwest Logo
5:40 pm - 10:20 pm
MKE
-
MDW
4h 40m
1 stop
Southwest Logo
9:50 am - 3:40 pm
MDW
-
MKE
5h 50m
1 stop
$163Southwest
Thu, Aug 6 - Thu, Aug 13
Delta Logo
6:57 am - 8:39 am
MSP
-
MDW
1h 42mnonstop
Delta Logo
7:25 pm - 9:10 pm
MDW
-
MSP
1h 45mnonstop
$195Delta
Tue, Aug 25 - Tue, Aug 25
Delta Logo
11:41 am - 6:01 pm
DLH
-
MDW
6h 20m
1 stop
Delta Logo
4:52 pm - 10:41 pm
MDW
-
DLH
5h 49m
1 stop
$258Delta
Tue, Sep 1 - Sat, Sep 5
Allegiant Air Logo
2:44 pm - 2:38 pm
ATW
-
MDW
23h 54m
2 stops
Allegiant Air Logo
9:08 am - 5:23 pm
MDW
-
ATW
8h 15m
1 stop
$448Allegiant Air
Thu, Jul 30 - Sun, Aug 2
Multiple Airlines Logo
2:44 pm - 5:22 pm
ATW
-
MDW
26h 38m
2 stops
Multiple Airlines Logo
9:14 am - 5:36 pm
MDW
-
ATW
8h 22m
1 stop
$458Multiple Airlines
Thu, Aug 6 - Thu, Aug 13
Multiple Airlines Logo
2:44 pm - 10:03 pm
ATW
-
MDW
31h 19m
2 stops
Multiple Airlines Logo
9:08 am - 5:23 pm
MDW
-
ATW
8h 15m
1 stop
$460Multiple Airlines
Thu, Jul 30 - Sun, Aug 2

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Southwest flights from Wisconsin to Chicago Midway Airport

Our best Southwest deals on Wisconsin to Chicago Midway Airport flight tickets
Southwest
Aug 6
MKE4:20 pmMilwaukee-Mitchell
0h 50m
MDW5:10 pmChicago Midway
Aug 10
MDW8:40 pmChicago Midway
0h 45m
MKE9:25 pmMilwaukee-Mitchell
$143
Southwest
Aug 6
MKE5:45 amMilwaukee-Mitchell
0h 45m
MDW6:30 amChicago Midway
Aug 10
MDW10:10 amChicago Midway
0h 50m
MKE11:00 amMilwaukee-Mitchell
$144
Southwest
Aug 6
MKE4:50 pmMilwaukee-Mitchell
5h 05m
1 stop
MDW9:55 pmChicago Midway
Aug 10
MDW8:40 pmChicago Midway
0h 45m
MKE9:25 pmMilwaukee-Mitchell
$153

Frontier flights from Wisconsin to Chicago Midway Airport

Our best Frontier deals on Wisconsin to Chicago Midway Airport flight tickets
Frontier
Aug 4
MSP2:24 pmMinneapolis St Paul
7h 39m
1 stop
MDW10:03 pmChicago Midway
Aug 11
MDW6:05 amChicago Midway
7h 34m
1 stop
MSP1:39 pmMinneapolis St Paul
$210
Frontier
Aug 19
MSP2:38 pmMinneapolis St Paul
8h 09m
1 stop
MDW10:47 pmChicago Midway
Aug 26
MDW6:05 amChicago Midway
7h 38m
1 stop
MSP1:43 pmMinneapolis St Paul
$213
Frontier
Jul 29
MSP2:24 pmMinneapolis St Paul
7h 39m
1 stop
MDW10:03 pmChicago Midway
Aug 4
MDW6:05 amChicago Midway
7h 34m
1 stop
MSP1:39 pmMinneapolis St Paul
$220

momondo Fare Finder

 
Customize your flight search to find flights from Wisconsin to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated July 10, 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

Thu 8/6

4:20 pm-5:10 pm

Nonstop0h 50m

Chicago Midway

Mon 8/10

8:40 pm-9:25 pm

Nonstop0h 45m

$143

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Thu 8/6

5:45 am-6:30 am

Nonstop0h 45m

Chicago Midway

Mon 8/10

10:10 am-11:00 am

Nonstop0h 50m

$144

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Thu 8/6

4:50 pm-9:55 pm

1 stop5h 05m

Chicago Midway

Mon 8/10

8:40 pm-9:25 pm

Nonstop0h 45m

$153

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Tue 8/4

6:40 am-7:30 am

Nonstop0h 50m

Chicago Midway

Tue 8/11

2:00 pm-7:55 pm

1 stop5h 55m

$154

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Thu 8/6

5:40 pm-10:20 pm

1 stop4h 40m

Chicago Midway

Thu 8/13

9:50 am-3:40 pm

1 stop5h 50m

$163

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 8/25

6:57 am-8:39 am

Nonstop1h 42m

Chicago Midway

Tue 8/25

7:25 pm-9:10 pm

Nonstop1h 45m

$195

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Tue 9/1

11:41 am-6:01 pm

1 stop6h 20m

Chicago Midway

Sat 9/5

4:52 pm-10:41 pm

1 stop5h 49m

$258

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

Thu 7/30

2:44 pm-2:38 pm

2 stops23h 54m

Chicago Midway

Sun 8/2

9:08 am-5:23 pm

1 stop8h 15m

$448

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

Thu 8/6

2:44 pm-5:22 pm

2 stops26h 38m

Chicago Midway

Thu 8/13

9:14 am-5:36 pm

1 stop8h 22m

$458

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

Thu 7/30

2:44 pm-10:03 pm

2 stops31h 19m

Chicago Midway

Sun 8/2

9:08 am-5:23 pm

1 stop8h 15m

$460

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Wisconsin to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Wisconsin. The lowest ticket price found for a Saturday departure recently was $404. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Wisconsin because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $457.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Wisconsin at noon is the least expensive time of day to depart. momondo users have found prices as low as $378 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $426. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Wisconsin to Chicago Midway flight route?

Fly from Milwaukee-Mitchell to Chicago Midway for the best Wisconsin - Chicago Midway flight prices

What cabin class options are available on Wisconsin to Chicago Midway Airport flights?

There is only 1 cabin class available to choose from on Wisconsin to Chicago Midway Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap Wisconsin to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Wisconsin to Chicago Midway Airport

Best Price Found

$168

Fastest flight time

0h 45m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Wisconsin in the past 72 hours is $168. The best round-trip flight deal from Wisconsin to Chicago Midway Airport found on momondo in the last 72 hours is $346.
The fastest flight from Wisconsin to Chicago Midway Airport takes 0h 45m
Direct flights go from Wisconsin to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Wisconsin to Chicago Midway Airport

  • When did momondo last update prices for flights from Wisconsin to Chicago Midway Airport?

    Prices for flights from Wisconsin to Chicago Midway Airport refresh daily.

  • How many operators does momondo search for flights from Wisconsin to Chicago Midway Airport?

  • How old do you have to be to fly from Wisconsin to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Wisconsin to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Wisconsin to Chicago Midway Airport?

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Wisconsin to Chicago?

Finding the right flight to Chicago from Wisconsin is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Wisconsin to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Wisconsin on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Wisconsin to Chicago?

momondo helps you find the best flight between Wisconsin and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Wisconsin to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Wisconsin to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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