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Cheap flights from Wisconsin to Chicago from $79

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 6/3. 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
4:30 pm - 9:50 pm
MSP
-
MDW
5h 20m
1 stop
Southwest Logo
4:40 pm - 10:30 pm
MDW
-
MSP
5h 50m
1 stop
$137Southwest
Tue, Jun 2 - Wed, Jun 3
Southwest Logo
7:50 am - 2:55 pm
MSP
-
MDW
7h 05m
1 stop
Southwest Logo
4:40 pm - 10:30 pm
MDW
-
MSP
5h 50m
1 stop
$142Southwest
Tue, Jun 2 - Tue, Jun 2
Delta Logo
7:00 am - 8:42 am
MSP
-
MDW
1h 42mnonstop
Delta Logo
9:23 am - 11:00 am
MDW
-
MSP
1h 37mnonstop
$147Delta
Mon, Jun 1 - Wed, Jun 3
Southwest Logo
7:10 am - 3:45 pm
MSP
-
MDW
8h 35m
2 stops
Southwest Logo
7:40 am - 9:10 am
MDW
-
MSP
1h 30mnonstop
$152Southwest
Wed, Jun 3 - Wed, Jun 10
Southwest Logo
5:20 am - 6:50 am
MSP
-
MDW
1h 30mnonstop
Southwest Logo
4:40 pm - 10:30 pm
MDW
-
MSP
5h 50m
1 stop
$157Southwest
Mon, Jun 1 - Wed, Jun 3
Southwest Logo
7:10 am - 3:45 pm
MSP
-
MDW
8h 35m
2 stops
Southwest Logo
4:50 pm - 11:05 pm
MDW
-
MSP
6h 15m
1 stop
$162Southwest
Wed, Jun 3 - Wed, Jun 3
Southwest Logo
6:05 pm - 7:40 pm
MSP
-
MDW
1h 35mnonstop
Southwest Logo
2:35 pm - 10:45 pm
MDW
-
MSP
8h 10m
1 stop
$163Southwest
Sat, Jun 6 - Tue, Jun 9
Delta Logo
5:15 am - 8:40 am
DLH
-
MDW
3h 25m
1 stop
Delta Logo
7:25 pm - 10:41 pm
MDW
-
DLH
3h 16m
1 stop
$258Delta
Thu, Aug 6 - Sat, Aug 8
Delta Logo
7:58 am - 1:19 pm
DLH
-
MDW
5h 21m
1 stop
Delta Logo
7:13 pm - 10:44 pm
MDW
-
DLH
3h 31m
1 stop
$273Delta
Sun, May 24 - Sat, May 30
Multiple Airlines Logo
9:41 am - 11:12 am
ATW
-
MDW
25h 31m
2 stops
Multiple Airlines Logo
9:11 am - 3:59 pm
MDW
-
ATW
6h 48m
1 stop
$475Multiple Airlines
Mon, Jun 15 - Thu, Jun 18

Delta flights from Wisconsin to Chicago Midway Airport

Our best Delta deals on Wisconsin to Chicago Midway Airport flight tickets
Delta
Jun 1
MSP7:00 amMinneapolis St Paul
1h 42m
MDW8:42 amChicago Midway
Jun 3
MDW9:23 amChicago Midway
1h 37m
MSP11:00 amMinneapolis St Paul
$147
Delta
Jun 17
MSP6:55 amMinneapolis St Paul
1h 42m
MDW8:37 amChicago Midway
Jun 17
MDW1:49 pmChicago Midway
1h 44m
MSP3:33 pmMinneapolis St Paul
$179
Delta
May 30
MSP4:20 pmMinneapolis St Paul
1h 36m
MDW5:56 pmChicago Midway
Jun 1
MDW9:23 amChicago Midway
1h 37m
MSP11:00 amMinneapolis St Paul
$188

Frontier flights from Wisconsin to Chicago Midway Airport

Our best Frontier deals on Wisconsin to Chicago Midway Airport flight tickets
Frontier
Jun 6
MSP2:22 pmMinneapolis St Paul
7h 40m
1 stop
MDW10:02 pmChicago Midway
Jun 10
MDW6:00 amChicago Midway
7h 39m
1 stop
MSP1:39 pmMinneapolis St Paul
$204
Frontier
Jul 4
MSP2:24 pmMinneapolis St Paul
7h 47m
1 stop
MDW10:11 pmChicago Midway
Jul 7
MDW6:00 amChicago Midway
7h 33m
1 stop
MSP1:33 pmMinneapolis St Paul
$210
Frontier
Aug 6
MSP2:24 pmMinneapolis St Paul
7h 44m
1 stop
MDW10:08 pmChicago Midway
Aug 20
MDW6:00 amChicago Midway
7h 39m
1 stop
MSP1:39 pmMinneapolis St Paul
$224

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 May 12, 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 6/2

4:30 pm-9:50 pm

1 stop5h 20m

Chicago Midway

Wed 6/3

4:40 pm-10:30 pm

1 stop5h 50m

$137

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 6/2

7:50 am-2:55 pm

1 stop7h 05m

Chicago Midway

Tue 6/2

4:40 pm-10:30 pm

1 stop5h 50m

$142
Quickest round-trip

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Mon 6/1

7:00 am-8:42 am

Nonstop1h 42m

Chicago Midway

Wed 6/3

9:23 am-11:00 am

Nonstop1h 37m

$147

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 6/3

7:10 am-3:45 pm

2 stops8h 35m

Chicago Midway

Wed 6/10

7:40 am-9:10 am

Nonstop1h 30m

$152

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Mon 6/1

5:20 am-6:50 am

Nonstop1h 30m

Chicago Midway

Wed 6/3

4:40 pm-10:30 pm

1 stop5h 50m

$157

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 6/3

7:10 am-3:45 pm

2 stops8h 35m

Chicago Midway

Wed 6/3

4:50 pm-11:05 pm

1 stop6h 15m

$162

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 6/6

6:05 pm-7:40 pm

Nonstop1h 35m

Chicago Midway

Tue 6/9

2:35 pm-10:45 pm

1 stop8h 10m

$163

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Thu 8/6

5:15 am-8:40 am

1 stop3h 25m

Chicago Midway

Sat 8/8

7:25 pm-10:41 pm

1 stop3h 16m

$258

DuluthChicago

DLH - MDW

DLHMDW

Duluth Intl

Sun 5/24

7:58 am-1:19 pm

1 stop5h 21m

Chicago Midway

Sat 5/30

7:13 pm-10:44 pm

1 stop3h 31m

$273

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

Mon 6/15

9:41 am-11:12 am

2 stops25h 31m

Chicago Midway

Thu 6/18

9:11 am-3:59 pm

1 stop6h 48m

$475

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, Wednesday is the cheapest day to fly to Chicago Midway Airport from Wisconsin. The lowest ticket price found for a Wednesday departure recently was $391. 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 $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 $424. 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

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

$211

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 $211. The best round-trip flight deal from Wisconsin to Chicago Midway Airport found on momondo in the last 72 hours is $344.
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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
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.

An easier way to manage your Chicago Midway Airport trip

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