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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 11/12. 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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Cheap round-trip flights

Delta Logo
8:50 am - 10:30 amMSP-MDW
1h 40mnonstop
Delta Logo
3:00 pm - 4:38 pmMDW-MSP
1h 38mnonstop
$97Delta
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Sat, Oct 18 - Sat, Oct 18
Southwest Logo
3:40 pm - 7:05 pmMSP-MDW
3h 25m1 stop
Southwest Logo
7:45 am - 9:10 amMDW-MSP
1h 25mnonstop
$107Southwest
Find Deal
Sat, Oct 18 - Tue, Oct 21
Southwest Logo
7:00 am - 4:50 pmMSP-MDW
9h 50m2 stops
Southwest Logo
7:45 am - 9:10 amMDW-MSP
1h 25mnonstop
$112Southwest
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Tue, Oct 21 - Thu, Oct 23
Southwest Logo
6:00 am - 2:25 pmMSP-MDW
8h 25m1 stop
Southwest Logo
7:45 am - 9:10 amMDW-MSP
1h 25mnonstop
$113Southwest
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Tue, Oct 21 - Thu, Oct 23
Delta Logo
7:14 am - 8:53 amMSP-MDW
1h 39mnonstop
Delta Logo
9:20 am - 11:02 amMDW-MSP
1h 42mnonstop
$115Delta
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Sun, Oct 5 - Wed, Oct 8
Southwest Logo
3:40 pm - 7:05 pmMSP-MDW
3h 25m1 stop
Southwest Logo
5:55 pm - 10:20 pmMDW-MSP
4h 25m1 stop
$117Southwest
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Sat, Oct 18 - Tue, Oct 21
Frontier Logo
11:29 am - 10:08 pmMSP-MDW
10h 39m1 stop
Frontier Logo
12:30 pm - 12:14 amMDW-MSP
11h 44m1 stop
$144Frontier
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Fri, Nov 14 - Sun, Nov 16
Frontier Logo
9:40 am - 4:00 pmMSP-MDW
6h 20m1 stop
Frontier Logo
10:13 am - 8:36 pmMDW-MSP
10h 23m1 stop
$154Frontier
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Mon, Sep 29 - Thu, Oct 2
Logo
5:43 pm - 11:46 pmMSP-MDW
6h 03m1 stop
Logo
8:05 am - 11:58 amMDW-MSP
27h 53m1 stop
$169
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Fri, Oct 17 - Tue, Oct 21
Logo
5:43 pm - 11:46 pmMSP-MDW
6h 03m1 stop
Logo
6:20 am - 11:27 pmMDW-MSP
17h 07m1 stop
$182
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Fri, Oct 24 - Sun, Oct 26

Southwest flights from Wisconsin to Chicago Midway Airport

Our best Southwest deals on Wisconsin to Chicago Midway Airport flight tickets
Southwest
Oct 18
MSP3:40 pmMinneapolis St Paul
3h 25m
1 stop
MDW7:05 pmChicago Midway
Oct 21
MDW7:45 amChicago Midway
1h 25m
MSP9:10 amMinneapolis St Paul
$107
Find similar
Southwest
Oct 21
MSP7:00 amMinneapolis St Paul
9h 50m
2 stops
MDW4:50 pmChicago Midway
Oct 23
MDW7:45 amChicago Midway
1h 25m
MSP9:10 amMinneapolis St Paul
$112
Find similar
Southwest
Oct 21
MSP6:00 amMinneapolis St Paul
8h 25m
1 stop
MDW2:25 pmChicago Midway
Oct 23
MDW7:45 amChicago Midway
1h 25m
MSP9:10 amMinneapolis St Paul
$113
Find similar

Delta flights from Wisconsin to Chicago Midway Airport

Our best Delta deals on Wisconsin to Chicago Midway Airport flight tickets
Delta
Oct 18
MSP8:50 amMinneapolis St Paul
1h 40m
MDW10:30 amChicago Midway
Oct 18
MDW3:00 pmChicago Midway
1h 38m
MSP4:38 pmMinneapolis St Paul
$97
Find similar
Delta
Oct 5
MSP7:14 amMinneapolis St Paul
1h 39m
MDW8:53 amChicago Midway
Oct 8
MDW9:20 amChicago Midway
1h 42m
MSP11:02 amMinneapolis St Paul
$115
Find similar
Delta
Oct 24
MSP4:08 pmMinneapolis St Paul
1h 35m
MDW5:43 pmChicago Midway
Oct 27
MDW9:20 amChicago Midway
1h 42m
MSP11:02 amMinneapolis St Paul
$120
Find similar

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 September 15, 2025.
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

Sat 10/18

8:50 am-10:30 am

Nonstop1h 40m

Chicago Midway

Sat 10/18

3:00 pm-4:38 pm

Nonstop1h 38m

$97

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 10/18

3:40 pm-7:05 pm

1 stop3h 25m

Chicago Midway

Tue 10/21

7:45 am-9:10 am

Nonstop1h 25m

$107

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 10/21

7:00 am-4:50 pm

2 stops9h 50m

Chicago Midway

Thu 10/23

7:45 am-9:10 am

Nonstop1h 25m

$112

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 10/21

6:00 am-2:25 pm

1 stop8h 25m

Chicago Midway

Thu 10/23

7:45 am-9:10 am

Nonstop1h 25m

$113

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sun 10/5

7:14 am-8:53 am

Nonstop1h 39m

Chicago Midway

Wed 10/8

9:20 am-11:02 am

Nonstop1h 42m

$115

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 10/18

3:40 pm-7:05 pm

1 stop3h 25m

Chicago Midway

Tue 10/21

5:55 pm-10:20 pm

1 stop4h 25m

$117

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Fri 11/14

11:29 am-10:08 pm

1 stop10h 39m

Chicago Midway

Sun 11/16

12:30 pm-12:14 am

1 stop11h 44m

$144

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Mon 9/29

9:40 am-4:00 pm

1 stop6h 20m

Chicago Midway

Thu 10/2

10:13 am-8:36 pm

1 stop10h 23m

$154

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Fri 10/17

5:43 pm-11:46 pm

1 stop6h 03m

Chicago Midway

Tue 10/21

8:05 am-11:58 am

1 stop27h 53m

$169

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Fri 10/24

5:43 pm-11:46 pm

1 stop6h 03m

Chicago Midway

Sun 10/26

6:20 am-11:27 pm

1 stop17h 07m

$182

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 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

Fastest flight time

1h 00m

Direct flights

Every day
The fastest flight from Wisconsin to Chicago Midway Airport takes 1h 00m
Direct flights go from Wisconsin to Chicago Midway Airport every day.
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  • 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.

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
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
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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