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Cheap flights from Wisconsin to Chicago from $59

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 4/14. 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

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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
6:55 am - 4:35 pm
MSP
-
MDW
9h 40m
2 stops
Southwest Logo
10:45 am - 12:20 pm
MDW
-
MSP
1h 35mnonstop
$112Southwest
Tue, Apr 7 - Tue, Apr 14
Southwest Logo
3:15 pm - 4:50 pm
MSP
-
MDW
1h 35mnonstop
Southwest Logo
9:05 pm - 10:35 pm
MDW
-
MSP
1h 30mnonstop
$117Southwest
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
7:10 am - 3:45 pm
MSP
-
MDW
8h 35m
2 stops
Southwest Logo
4:40 pm - 10:30 pm
MDW
-
MSP
5h 50m
1 stop
$122Southwest
Tue, Apr 7 - Tue, Apr 14
Southwest Logo
8:20 am - 9:50 am
MSP
-
MDW
1h 30mnonstop
Southwest Logo
6:20 pm - 7:50 pm
MDW
-
MSP
1h 30mnonstop
$127Southwest
Mon, Apr 13 - Wed, Apr 15
Southwest Logo
8:40 am - 4:35 pm
MSP
-
MDW
7h 55m
2 stops
Southwest Logo
10:45 am - 12:20 pm
MDW
-
MSP
1h 35mnonstop
$132Southwest
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
4:55 pm - 11:30 pm
MSP
-
MDW
6h 35m
1 stop
Southwest Logo
9:05 pm - 10:35 pm
MDW
-
MSP
1h 30mnonstop
$137Southwest
Mon, Apr 13 - Wed, Apr 15
Delta Logo
5:07 pm - 6:40 pm
MSP
-
MDW
1h 33mnonstop
Delta Logo
9:46 am - 11:27 am
MDW
-
MSP
1h 41mnonstop
$147Delta
Wed, Apr 8 - Sat, Apr 25
Delta Logo
5:10 am - 8:38 am
DLH
-
MDW
3h 28m
1 stop
Delta Logo
6:45 pm - 11:38 pm
MDW
-
DLH
4h 53m
1 stop
$238Delta
Wed, Jun 10 - Sat, Jun 13
Delta Logo
5:10 am - 8:38 am
DLH
-
MDW
3h 28m
1 stop
Delta Logo
6:45 pm - 11:38 pm
MDW
-
DLH
4h 53m
1 stop
$258Delta
Wed, Jun 10 - Sat, Jun 13
Multiple Airlines Logo
6:30 am - 8:07 pm
ATW
-
MDW
37h 37m
2 stops
Multiple Airlines Logo
9:04 am - 10:17 pm
MDW
-
ATW
13h 13m
1 stop
$453Multiple Airlines
Sun, Apr 12 - Sun, Apr 19

Delta flights from Wisconsin to Chicago Midway Airport

Our best Delta deals on Wisconsin to Chicago Midway Airport flight tickets
Delta
Apr 8
MSP5:07 pmMinneapolis St Paul
1h 33m
MDW6:40 pmChicago Midway
Apr 25
MDW9:46 amChicago Midway
1h 41m
MSP11:27 amMinneapolis St Paul
$147
Delta
Apr 11
MSP7:00 amMinneapolis St Paul
1h 50m
MDW8:50 amChicago Midway
Apr 15
MDW2:12 pmChicago Midway
1h 43m
MSP3:55 pmMinneapolis St Paul
$177
Delta
Apr 7
MSP5:07 pmMinneapolis St Paul
1h 33m
MDW6:40 pmChicago Midway
Apr 24
MDW9:29 amChicago Midway
1h 41m
MSP11:10 amMinneapolis St Paul
$182

Southwest flights from Wisconsin to Chicago Midway Airport

Our best Southwest deals on Wisconsin to Chicago Midway Airport flight tickets
Southwest
Apr 7
MSP6:55 amMinneapolis St Paul
9h 40m
2 stops
MDW4:35 pmChicago Midway
Apr 14
MDW10:45 amChicago Midway
1h 35m
MSP12:20 pmMinneapolis St Paul
$112
Southwest
Apr 14
MSP3:15 pmMinneapolis St Paul
1h 35m
MDW4:50 pmChicago Midway
Apr 21
MDW9:05 pmChicago Midway
1h 30m
MSP10:35 pmMinneapolis St Paul
$117
Southwest
Apr 7
MSP7:10 amMinneapolis St Paul
8h 35m
2 stops
MDW3:45 pmChicago Midway
Apr 14
MDW4:40 pmChicago Midway
5h 50m
1 stop
MSP10:30 pmMinneapolis St Paul
$122

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 March 17, 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

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 4/7

6:55 am-4:35 pm

2 stops9h 40m

Chicago Midway

Tue 4/14

10:45 am-12:20 pm

Nonstop1h 35m

$112

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 4/14

3:15 pm-4:50 pm

Nonstop1h 35m

Chicago Midway

Tue 4/21

9:05 pm-10:35 pm

Nonstop1h 30m

$117

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 4/7

7:10 am-3:45 pm

2 stops8h 35m

Chicago Midway

Tue 4/14

4:40 pm-10:30 pm

1 stop5h 50m

$122
Quickest round-trip

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Mon 4/13

8:20 am-9:50 am

Nonstop1h 30m

Chicago Midway

Wed 4/15

6:20 pm-7:50 pm

Nonstop1h 30m

$127

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 4/14

8:40 am-4:35 pm

2 stops7h 55m

Chicago Midway

Tue 4/21

10:45 am-12:20 pm

Nonstop1h 35m

$132

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Mon 4/13

4:55 pm-11:30 pm

1 stop6h 35m

Chicago Midway

Wed 4/15

9:05 pm-10:35 pm

Nonstop1h 30m

$137

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 4/8

5:07 pm-6:40 pm

Nonstop1h 33m

Chicago Midway

Sat 4/25

9:46 am-11:27 am

Nonstop1h 41m

$147

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Wed 6/10

5:10 am-8:38 am

1 stop3h 28m

Chicago Midway

Sat 6/13

6:45 pm-11:38 pm

1 stop4h 53m

$238

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Wed 6/10

5:10 am-8:38 am

1 stop3h 28m

Chicago Midway

Sat 6/13

6:45 pm-11:38 pm

1 stop4h 53m

$258

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

Sun 4/12

6:30 am-8:07 pm

2 stops37h 37m

Chicago Midway

Sun 4/19

9:04 am-10:17 pm

1 stop13h 13m

$453

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, Monday is the cheapest day to fly to Chicago Midway Airport from Wisconsin. The lowest ticket price found for a Monday departure recently was $389. 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 $446.

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 $386 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $431. 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

$178

Fastest flight time

0h 50m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Wisconsin in the past 72 hours is $178. The best round-trip flight deal from Wisconsin to Chicago Midway Airport found on momondo in the last 72 hours is $358.
The fastest flight from Wisconsin to Chicago Midway Airport takes 0h 50m
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
Valparaiso
Schererville
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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