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Cheap flights from Wisconsin to Chicago from $125

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Wisconsin to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:45 am - 6:50 amMKE  Milwaukee-Mitchell-MDW Chicago Midway
1h 05mnonstop
Southwest Logo
10:10 am - 11:00 amMDW  Chicago Midway-MKE Milwaukee-Mitchell
0h 50mnonstop
$174Southwest
Sat, Nov 14 - Sat, Nov 21
Southwest Logo
1:45 pm - 2:40 pmMKE  Milwaukee-Mitchell-MDW Chicago Midway
0h 55mnonstop
Southwest Logo
6:55 pm - 12:20 amMDW  Chicago Midway-MKE Milwaukee-Mitchell
5h 25m2 stops Louisville Intl Nashville Intl
$189Southwest
Sat, Nov 14 - Sat, Nov 21
Southwest Logo
6:15 am - 1:30 pmMKE  Milwaukee-Mitchell-MDW Chicago Midway
7h 15m1 stop Lambert-St Louis
Southwest Logo
10:10 am - 11:00 amMDW  Chicago Midway-MKE Milwaukee-Mitchell
0h 50mnonstop
$189Southwest
Sat, Nov 14 - Sat, Nov 21
Southwest Logo
6:15 am - 1:30 pmMKE  Milwaukee-Mitchell-MDW Chicago Midway
7h 15m1 stop Lambert-St Louis
Southwest Logo
6:55 pm - 12:20 amMDW  Chicago Midway-MKE Milwaukee-Mitchell
5h 25m2 stops Louisville Intl Nashville Intl
$205Southwest
Sat, Nov 14 - Sat, Nov 21
Southwest Logo
5:30 am - 6:35 amMKE  Milwaukee-Mitchell-MDW Chicago Midway
1h 05mnonstop
Southwest Logo
6:30 am - 9:40 amMDW  Chicago Midway-MKE Milwaukee-Mitchell
3h 10m1 stop Lambert-St Louis
$220Southwest
Thu, Nov 12 - Sun, Nov 15
Southwest Logo
5:30 am - 6:35 amMKE  Milwaukee-Mitchell-MDW Chicago Midway
1h 05mnonstop
Southwest Logo
10:10 am - 11:00 amMDW  Chicago Midway-MKE Milwaukee-Mitchell
0h 50mnonstop
$222Southwest
Thu, Nov 12 - Sun, Nov 15
Southwest Logo
5:50 pm - 10:45 pmMKE  Milwaukee-Mitchell-MDW Chicago Midway
4h 55m1 stop Lambert-St Louis
Southwest Logo
6:30 am - 9:40 amMDW  Chicago Midway-MKE Milwaukee-Mitchell
3h 10m1 stop Lambert-St Louis
$229Southwest
Thu, Nov 12 - Sun, Nov 15
Southwest Logo
5:30 am - 6:35 amMKE  Milwaukee-Mitchell-MDW Chicago Midway
1h 05mnonstop
Southwest Logo
10:10 am - 11:00 amMDW  Chicago Midway-MKE Milwaukee-Mitchell
0h 50mnonstop
$249Southwest
Fri, Nov 20 - Sat, Nov 21
Southwest Logo
4:50 pm - 5:40 pmMKE  Milwaukee-Mitchell-MDW Chicago Midway
0h 50mnonstop
Southwest Logo
10:10 am - 11:00 amMDW  Chicago Midway-MKE Milwaukee-Mitchell
0h 50mnonstop
$249Southwest
Thu, Nov 12 - Thu, Nov 19
Southwest Logo
6:20 am - 7:20 amMKE  Milwaukee-Mitchell-MDW Chicago Midway
1h 00mnonstop
Southwest Logo
9:10 pm - 10:15 pmMDW  Chicago Midway-MKE Milwaukee-Mitchell
1h 05mnonstop
$249Southwest
Tue, Nov 10 - Tue, Nov 17

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Delta flights from Wisconsin to Chicago Midway Airport

Our best Delta deals on Wisconsin to Chicago Midway Airport flight tickets
Delta
Mar 3
RHI12:25 pmRhinelander Oneida County
4h 25m
1 stop
MDW4:50 pmChicago Midway
Mar 6
MDW5:35 pmChicago Midway
3h 30m
1 stop
RHI9:05 pmRhinelander Oneida County
$425
Delta
Mar 3
RHI6:31 amRhinelander Oneida County
5h 20m
1 stop
MDW11:51 amChicago Midway
Mar 6
MDW1:00 pmChicago Midway
8h 05m
2 stops
RHI9:05 pmRhinelander Oneida County
$435
Delta
Oct 30
RHI10:50 amRhinelander Oneida County
5h 57m
1 stop
MDW4:47 pmChicago Midway
Nov 3
MDW5:31 pmChicago Midway
3h 22m
1 stop
RHI8:53 pmRhinelander Oneida County
$497

Southwest flights from Wisconsin to Chicago Midway Airport

Our best Southwest deals on Wisconsin to Chicago Midway Airport flight tickets
Southwest
Nov 14
MKE5:45 amMilwaukee-Mitchell
1h 05m
MDW6:50 amChicago Midway
Nov 21
MDW10:10 amChicago Midway
0h 50m
MKE11:00 amMilwaukee-Mitchell
$174
Southwest
Nov 14
MKE1:45 pmMilwaukee-Mitchell
0h 55m
MDW2:40 pmChicago Midway
Nov 21
MDW6:55 pmChicago Midway
5h 25m
2 stops
MKE12:20 amMilwaukee-Mitchell
$189
Southwest
Nov 14
MKE6:15 amMilwaukee-Mitchell
7h 15m
1 stop
MDW1:30 pmChicago Midway
Nov 21
MDW6:55 pmChicago Midway
5h 25m
2 stops
MKE12:20 amMilwaukee-Mitchell
$205

momondo Fare Finder

 
Use the filters below to find and compare flights from Wisconsin to Chicago Midway Airport that are best for you.

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Route

Depart

Return

Price

Cheapest round-trip

MilwaukeeChicago

MKE Milwaukee-Mitchell - MDW Chicago Midway

MKEMDW

Milwaukee-Mitchell

Sat 11/14

5:45 am-6:50 am

Nonstop1h 05m

Chicago Midway

Sat 11/21

10:10 am-11:00 am

Nonstop0h 50m

$174

MilwaukeeChicago

MKE Milwaukee-Mitchell - MDW Chicago Midway

MKEMDW

Milwaukee-Mitchell

Sat 11/14

1:45 pm-2:40 pm

Nonstop0h 55m

Chicago Midway

Sat 11/21

6:55 pm-12:20 am

2 stops5h 25m

$189

MilwaukeeChicago

MKE Milwaukee-Mitchell - MDW Chicago Midway

MKEMDW

Milwaukee-Mitchell

Sat 11/14

6:15 am-1:30 pm

1 stop7h 15m

Chicago Midway

Sat 11/21

10:10 am-11:00 am

Nonstop0h 50m

$189

MilwaukeeChicago

MKE Milwaukee-Mitchell - MDW Chicago Midway

MKEMDW

Milwaukee-Mitchell

Sat 11/14

6:15 am-1:30 pm

1 stop7h 15m

Chicago Midway

Sat 11/21

6:55 pm-12:20 am

2 stops5h 25m

$205

MilwaukeeChicago

MKE Milwaukee-Mitchell - MDW Chicago Midway

MKEMDW

Milwaukee-Mitchell

Thu 11/12

5:30 am-6:35 am

Nonstop1h 05m

Chicago Midway

Sun 11/15

6:30 am-9:40 am

1 stop3h 10m

$220

MilwaukeeChicago

MKE Milwaukee-Mitchell - MDW Chicago Midway

MKEMDW

Milwaukee-Mitchell

Thu 11/12

5:30 am-6:35 am

Nonstop1h 05m

Chicago Midway

Sun 11/15

10:10 am-11:00 am

Nonstop0h 50m

$222

MilwaukeeChicago

MKE Milwaukee-Mitchell - MDW Chicago Midway

MKEMDW

Milwaukee-Mitchell

Thu 11/12

5:50 pm-10:45 pm

1 stop4h 55m

Chicago Midway

Sun 11/15

6:30 am-9:40 am

1 stop3h 10m

$229

MilwaukeeChicago

MKE Milwaukee-Mitchell - MDW Chicago Midway

MKEMDW

Milwaukee-Mitchell

Fri 11/20

5:30 am-6:35 am

Nonstop1h 05m

Chicago Midway

Sat 11/21

10:10 am-11:00 am

Nonstop0h 50m

$249
Quickest round-trip

MilwaukeeChicago

MKE Milwaukee-Mitchell - MDW Chicago Midway

MKEMDW

Milwaukee-Mitchell

Thu 11/12

4:50 pm-5:40 pm

Nonstop0h 50m

Chicago Midway

Thu 11/19

10:10 am-11:00 am

Nonstop0h 50m

$249

MilwaukeeChicago

MKE Milwaukee-Mitchell - MDW Chicago Midway

MKEMDW

Milwaukee-Mitchell

Tue 11/10

6:20 am-7:20 am

Nonstop1h 00m

Chicago Midway

Tue 11/17

9:10 pm-10:15 pm

Nonstop1h 05m

$249

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 $402. 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 $436.

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 $385 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $421. 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 Airport flights?

There is only 1 cabin class available to choose from on Wisconsin to Chicago Midway Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Wisconsin to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Wisconsin to Chicago Midway Airport.

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

$125

Fastest flight time

0h 50m

Direct flights

Mon, Tue, Wed, Fri, Sat and Sun
The best one-way flight to Chicago Midway Airport from Wisconsin in the past 72 hours is $125. The best round-trip flight deal from Wisconsin to Chicago Midway Airport found on momondo in the last 72 hours is $174.
The fastest flight from Wisconsin to Chicago Midway Airport takes 0h 50m
Direct flights go from Wisconsin to Chicago Midway Airport on Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
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 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
Portage
Saint Joseph
Benton Harbor
Lansing
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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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