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Cheap flights from Wisconsin to Chicago from $49

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 12/24. 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

Enter your travel dates to find the best prices.
Delta Logo
7:24 am - 9:19 amMSP-MDW
1h 55mnonstop
Delta Logo
1:50 pm - 3:30 pmMDW-MSP
1h 40mnonstop
$101Delta
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Wed, Dec 10 - Sat, Dec 13
Delta Logo
4:30 pm - 6:18 pmMSP-MDW
1h 48mnonstop
Delta Logo
9:59 am - 11:42 amMDW-MSP
1h 43mnonstop
$102Delta
Find Deal
Fri, Dec 5 - Mon, Dec 8
Southwest Logo
5:00 am - 6:45 amMSP-MDW
1h 45mnonstop
Southwest Logo
11:25 am - 12:55 pmMDW-MSP
1h 30mnonstop
$107Southwest
Find Deal
Tue, Dec 23 - Thu, Dec 25
Delta Logo
3:30 pm - 5:19 pmMSP-MDW
1h 49mnonstop
Delta Logo
11:48 am - 1:32 pmMDW-MSP
1h 44mnonstop
$109Delta
Find Deal
Wed, Dec 24 - Thu, Jan 1
Southwest Logo
5:30 am - 11:25 amMSP-MDW
5h 55m1 stop
Southwest Logo
1:45 pm - 3:15 pmMDW-MSP
1h 30mnonstop
$111Southwest
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Wed, Dec 3 - Wed, Dec 3
Southwest Logo
5:45 am - 12:30 pmMSP-MDW
6h 45m2 stops
Southwest Logo
8:45 pm - 10:15 pmMDW-MSP
1h 30mnonstop
$116Southwest
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Wed, Dec 3 - Mon, Dec 8
Frontier Logo
7:07 pm - 11:08 amMSP-MDW
16h 01m1 stop
Frontier Logo
12:18 pm - 12:02 amMDW-MSP
11h 44m1 stop
$141Frontier
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Thu, Dec 4 - Mon, Dec 8
Frontier Logo
6:45 am - 8:02 pmMSP-MDW
13h 17m1 stop
Frontier Logo
6:00 am - 9:40 pmMDW-MSP
15h 40m2 stops
$158Frontier
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Fri, Jan 9 - Mon, Jan 12
Multiple Airlines Logo
2:40 pm - 1:05 amMSN-MDW
34h 25m2 stops
Multiple Airlines Logo
3:31 pm - 8:53 amMDW-MSN
17h 22m1 stop
$390Multiple Airlines
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Thu, Nov 20 - Mon, Nov 24
Multiple Airlines Logo
3:14 pm - 4:30 pmATW-MDW
25h 16m1 stop
Multiple Airlines Logo
5:30 am - 10:58 pmMDW-ATW
17h 28m2 stops
$497Multiple Airlines
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Wed, Nov 26 - Mon, Dec 1

Delta flights from Wisconsin to Chicago Midway Airport

Our best Delta deals on Wisconsin to Chicago Midway Airport flight tickets
Delta
Dec 10
MSP7:24 amMinneapolis St Paul
1h 55m
MDW9:19 amChicago Midway
Dec 13
MDW1:50 pmChicago Midway
1h 40m
MSP3:30 pmMinneapolis St Paul
$101
Find similar
Delta
Dec 5
MSP4:30 pmMinneapolis St Paul
1h 48m
MDW6:18 pmChicago Midway
Dec 8
MDW9:59 amChicago Midway
1h 43m
MSP11:42 amMinneapolis St Paul
$102
Find similar
Delta
Dec 24
MSP3:30 pmMinneapolis St Paul
1h 49m
MDW5:19 pmChicago Midway
Jan 1
MDW11:48 amChicago Midway
1h 44m
MSP1:32 pmMinneapolis St Paul
$109
Find similar

Southwest flights from Wisconsin to Chicago Midway Airport

Our best Southwest deals on Wisconsin to Chicago Midway Airport flight tickets
Southwest
Dec 23
MSP5:00 amMinneapolis St Paul
1h 45m
MDW6:45 amChicago Midway
Dec 25
MDW11:25 amChicago Midway
1h 30m
MSP12:55 pmMinneapolis St Paul
$107
Find similar
Southwest
Dec 3
MSP5:30 amMinneapolis St Paul
5h 55m
1 stop
MDW11:25 amChicago Midway
Dec 3
MDW1:45 pmChicago Midway
1h 30m
MSP3:15 pmMinneapolis St Paul
$111
Find similar
Southwest
Dec 3
MSP5:45 amMinneapolis St Paul
6h 45m
2 stops
MDW12:30 pmChicago Midway
Dec 8
MDW8:45 pmChicago Midway
1h 30m
MSP10:15 pmMinneapolis St Paul
$116
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 November 6, 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

Wed 12/10

7:24 am-9:19 am

Nonstop1h 55m

Chicago Midway

Sat 12/13

1:50 pm-3:30 pm

Nonstop1h 40m

$101

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Fri 12/5

4:30 pm-6:18 pm

Nonstop1h 48m

Chicago Midway

Mon 12/8

9:59 am-11:42 am

Nonstop1h 43m

$102

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 12/23

5:00 am-6:45 am

Nonstop1h 45m

Chicago Midway

Thu 12/25

11:25 am-12:55 pm

Nonstop1h 30m

$107

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 12/24

3:30 pm-5:19 pm

Nonstop1h 49m

Chicago Midway

Thu 1/1

11:48 am-1:32 pm

Nonstop1h 44m

$109

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 12/3

5:30 am-11:25 am

1 stop5h 55m

Chicago Midway

Wed 12/3

1:45 pm-3:15 pm

Nonstop1h 30m

$111

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Wed 12/3

5:45 am-12:30 pm

2 stops6h 45m

Chicago Midway

Mon 12/8

8:45 pm-10:15 pm

Nonstop1h 30m

$116

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 12/4

7:07 pm-11:08 am

1 stop16h 01m

Chicago Midway

Mon 12/8

12:18 pm-12:02 am

1 stop11h 44m

$141

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Fri 1/9

6:45 am-8:02 pm

1 stop13h 17m

Chicago Midway

Mon 1/12

6:00 am-9:40 pm

2 stops15h 40m

$158

MadisonChicago

MSN - MDW

MSNMDW

Madison Truax Field

Thu 11/20

2:40 pm-1:05 am

2 stops34h 25m

Chicago Midway

Mon 11/24

3:31 pm-8:53 am

1 stop17h 22m

$390

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

Wed 11/26

3:14 pm-4:30 pm

1 stop25h 16m

Chicago Midway

Mon 12/1

5:30 am-10:58 pm

2 stops17h 28m

$497

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

Best Price Found

$386

Fastest flight time

0h 55m

Direct flights

Every day
The best flight deal from Wisconsin to Chicago Midway Airport found on momondo in the last 72 hours is $386
The fastest flight from Wisconsin to Chicago Midway Airport takes 0h 55m
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
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.

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