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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 4/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Wisconsin to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:00 pm - 7:30 pm
MSP
-
MDW
1h 30mnonstop
Southwest Logo
7:40 am - 9:10 am
MDW
-
MSP
1h 30mnonstop
$128Southwest
Wed, Mar 11 - Sat, Mar 14
Delta Logo
7:05 am - 8:51 am
MSP
-
MDW
1h 46mnonstop
Delta Logo
9:31 am - 11:10 am
MDW
-
MSP
1h 39mnonstop
$134Delta
Wed, Apr 15 - Thu, Apr 16
Southwest Logo
4:20 pm - 10:50 pm
MSP
-
MDW
6h 30m
1 stop
Southwest Logo
7:40 am - 9:10 am
MDW
-
MSP
1h 30mnonstop
$138Southwest
Wed, Mar 11 - Sat, Mar 14
Southwest Logo
10:35 am - 7:30 pm
MSP
-
MDW
8h 55m
2 stops
Southwest Logo
7:40 am - 9:10 am
MDW
-
MSP
1h 30mnonstop
$143Southwest
Wed, Mar 11 - Sat, Mar 14
Southwest Logo
10:40 am - 4:15 pm
MSP
-
MDW
5h 35m
1 stop
Southwest Logo
10:15 am - 11:50 am
MDW
-
MSP
1h 35mnonstop
$144Southwest
Wed, Apr 15 - Thu, Apr 16
Southwest Logo
7:25 am - 11:40 am
MSP
-
MDW
4h 15m
1 stop
Southwest Logo
10:10 am - 11:40 am
MDW
-
MSP
1h 30mnonstop
$148Southwest
Wed, Apr 1 - Sat, Apr 4
Southwest Logo
7:10 am - 3:45 pm
MSP
-
MDW
8h 35m
2 stops
Southwest Logo
4:05 pm - 5:35 pm
MDW
-
MSP
1h 30mnonstop
$149Southwest
Wed, Apr 15 - Thu, Apr 16
Frontier Logo
8:11 pm - 7:07 pm
MKE
-
MDW
22h 56m
2 stops
Frontier Logo
9:51 pm - 5:50 pm
MDW
-
MKE
19h 59m
1 stop
$268Frontier
Mon, Mar 2 - Mon, Mar 9
Multiple Airlines Logo
6:00 am - 10:29 pm
ATW
-
MDW
40h 29m
2 stops
Multiple Airlines Logo
7:30 am - 9:17 pm
MDW
-
ATW
13h 47m
1 stop
$460Multiple Airlines
Sun, Feb 15 - Thu, Feb 19
Multiple Airlines Logo
6:00 am - 10:25 pm
ATW
-
MDW
16h 25m
2 stops
Multiple Airlines Logo
7:30 am - 9:17 pm
MDW
-
ATW
13h 47m
1 stop
$472Multiple Airlines
Sun, Feb 15 - Thu, Feb 19

Frontier flights from Wisconsin to Chicago Midway Airport

Our best Frontier deals on Wisconsin to Chicago Midway Airport flight tickets
Frontier
Apr 16
MSP10:45 amMinneapolis St Paul
21h 19m
1 stop
MDW8:04 amChicago Midway
Apr 19
MDW9:14 amChicago Midway
24h 36m
1 stop
MSP9:50 amMinneapolis St Paul
$195
Frontier
Feb 17
MSP9:30 amMinneapolis St Paul
33h 37m
2 stops
MDW7:07 pmChicago Midway
Feb 20
MDW7:45 amChicago Midway
11h 40m
1 stop
MSP7:25 pmMinneapolis St Paul
$223
Frontier
Feb 15
MSP12:26 pmMinneapolis St Paul
7h 33m
1 stop
MDW7:59 pmChicago Midway
Feb 23
MDW8:15 amChicago Midway
10h 59m
1 stop
MSP7:14 pmMinneapolis St Paul
$226

Delta flights from Wisconsin to Chicago Midway Airport

Our best Delta deals on Wisconsin to Chicago Midway Airport flight tickets
Delta
Apr 15
MSP7:05 amMinneapolis St Paul
1h 46m
MDW8:51 amChicago Midway
Apr 16
MDW9:31 amChicago Midway
1h 39m
MSP11:10 amMinneapolis St Paul
$134
Delta
Apr 8
MSP11:49 amMinneapolis St Paul
1h 36m
MDW1:25 pmChicago Midway
Apr 14
MDW9:31 amChicago Midway
1h 39m
MSP11:10 amMinneapolis St Paul
$171
Delta
Apr 8
MSP7:00 amMinneapolis St Paul
1h 50m
MDW8:50 amChicago Midway
Apr 10
MDW7:20 pmChicago Midway
1h 40m
MSP9:00 pmMinneapolis St Paul
$181

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 February 2, 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

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 3/11

6:00 pm-7:30 pm

Nonstop1h 30m

Chicago Midway

Sat 3/14

7:40 am-9:10 am

Nonstop1h 30m

$128

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 4/15

7:05 am-8:51 am

Nonstop1h 46m

Chicago Midway

Thu 4/16

9:31 am-11:10 am

Nonstop1h 39m

$134

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

$138

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 3/11

10:35 am-7:30 pm

2 stops8h 55m

Chicago Midway

Sat 3/14

7:40 am-9:10 am

Nonstop1h 30m

$143

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 4/15

10:40 am-4:15 pm

1 stop5h 35m

Chicago Midway

Thu 4/16

10:15 am-11:50 am

Nonstop1h 35m

$144

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 4/1

7:25 am-11:40 am

1 stop4h 15m

Chicago Midway

Sat 4/4

10:10 am-11:40 am

Nonstop1h 30m

$148

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 4/15

7:10 am-3:45 pm

2 stops8h 35m

Chicago Midway

Thu 4/16

4:05 pm-5:35 pm

Nonstop1h 30m

$149

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Mon 3/2

8:11 pm-7:07 pm

2 stops22h 56m

Chicago Midway

Mon 3/9

9:51 pm-5:50 pm

1 stop19h 59m

$268

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

Sun 2/15

6:00 am-10:29 pm

2 stops40h 29m

Chicago Midway

Thu 2/19

7:30 am-9:17 pm

1 stop13h 47m

$460

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

Sun 2/15

6:00 am-10:25 pm

2 stops16h 25m

Chicago Midway

Thu 2/19

7:30 am-9:17 pm

1 stop13h 47m

$472

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 $387. 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, Friday 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 $491.

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 $387 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 flights?

There is only 1 cabin class available to choose from on Wisconsin to Chicago Midway 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

$218

Fastest flight time

1h 25m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Wisconsin in the past 72 hours is $218. The best round-trip flight deal from Wisconsin to Chicago Midway Airport found on momondo in the last 72 hours is $347.
The fastest flight from Wisconsin to Chicago Midway Airport takes 1h 25m
Direct flights go from Wisconsin to Chicago Midway Airport every day.
Search flight deals

  • 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
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
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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