What is the cheapest airline that flies from Chicago Midway to Wisconsin?

Southwest and Delta are the most popular carriers operating from Chicago Midway to Wisconsin

When did momondo last update prices for flights from Chicago Midway Airport to Wisconsin?

Prices for flights from Chicago Midway Airport to Wisconsin are refreshed on a daily basis.

How old do you have to be to fly from Chicago Midway Airport to Wisconsin?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Wisconsin.

What documentation or ID do you need to fly to Wisconsin?

The travel and health documents required for your trip to Wisconsin can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Wisconsin. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$105 Cheap Flights from Chicago Midway Airport to Wisconsin in 2026/27

Q: How many flights depart from Chicago Midway Airport to Wisconsin on average per week?

5 flights are operational weekly from Chicago Midway Airport to Wisconsin as of October 2026. The most popular departure day for this route is Sat, with 40% of flights per week taking off on this day.

Find the cheapest flights from Chicago Midway Airport to Wisconsin

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:10 pm - 10:15 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

1h 05mnonstop

5:30 am - 6:35 amMKE Milwaukee-Mitchell-MDW Chicago Midway

1h 05mnonstop

$209Southwest

Tue, Nov 10 - Thu, Nov 12

9:15 pm - 10:15 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

1h 00mnonstop

6:20 am - 7:20 amMKE Milwaukee-Mitchell-MDW Chicago Midway

1h 00mnonstop

$209Southwest

Thu, Nov 12 - Wed, Nov 18

9:40 pm - 10:35 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 55mnonstop

4:50 pm - 5:40 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 50mnonstop

$209Southwest

Thu, Oct 29 - Thu, Nov 5

9:15 pm - 10:10 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 55mnonstop

6:20 am - 7:20 amMKE Milwaukee-Mitchell-MDW Chicago Midway

1h 00mnonstop

$209Southwest

Mon, Nov 2 - Wed, Nov 4

10:20 am - 11:05 amMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 45mnonstop

4:15 pm - 5:10 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 55mnonstop

$209Southwest

Wed, Oct 28 - Wed, Nov 4

10:40 am - 11:25 amMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 45mnonstop

5:45 am - 6:50 amMKE Milwaukee-Mitchell-MDW Chicago Midway

1h 05mnonstop

$209Southwest

Sat, Oct 31 - Sat, Nov 7

6:05 am - 11:15 amMDW Chicago Midway-MKE Milwaukee-Mitchell

5h 10m1 stop Lambert-St Louis

1:45 pm - 2:40 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 55mnonstop

$219Southwest

Sat, Oct 31 - Sat, Nov 7

10:20 am - 11:05 amMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 45mnonstop

8:00 am - 12:05 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

4h 05m1 stop Lambert-St Louis

$219Southwest

Wed, Oct 28 - Wed, Nov 4

6:30 pm - 11:55 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

5h 25m1 stop Nashville Intl

6:20 am - 7:20 amMKE Milwaukee-Mitchell-MDW Chicago Midway

1h 00mnonstop

$219Southwest

Mon, Nov 2 - Wed, Nov 4

10:05 am - 3:15 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

5h 10m1 stop Kansas City

4:50 pm - 5:40 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 50mnonstop

$219Southwest

Tue, Nov 10 - Thu, Nov 12

Cheap last minute flights

Enter your travel dates to find the best prices.

10:25 am - 11:10 amMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 45mnonstop

5:55 am - 6:45 amMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 50mnonstop

$398Southwest

Sat, Oct 10 - Fri, Oct 16

10:25 am - 11:10 amMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 45mnonstop

5:50 pm - 11:10 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

5h 20m1 stop Lambert-St Louis

$408Southwest

Sat, Oct 10 - Fri, Oct 16

10:25 am - 4:00 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

5h 35m2 stops Grand Rapids Gerald R. Ford Intl Nashville Intl

5:55 am - 6:45 amMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 50mnonstop

$413Southwest

Sat, Oct 10 - Fri, Oct 16

10:25 am - 4:00 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

5h 35m2 stops Grand Rapids Gerald R. Ford Intl Nashville Intl

5:50 pm - 11:10 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

5h 20m1 stop Lambert-St Louis

$423Southwest

Sat, Oct 10 - Fri, Oct 16

10:25 am - 11:10 amMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 45mnonstop

2:05 pm - 2:55 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 50mnonstop

$489Southwest

Sat, Oct 10 - Sat, Oct 10

8:45 pm - 9:35 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 50mnonstop

4:00 pm - 4:50 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 50mnonstop

$489Southwest

Tue, Oct 6 - Wed, Oct 7

10:25 am - 11:10 amMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 45mnonstop

2:50 pm - 5:45 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

2h 55m1 stop Lambert-St Louis

$499Southwest

Sat, Oct 10 - Sat, Oct 10

10:20 am - 11:05 amMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 45mnonstop

8:20 am - 12:05 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

3h 45m1 stop Lambert-St Louis

$499Southwest

Tue, Oct 6 - Wed, Oct 7

10:20 am - 11:05 amMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 45mnonstop

5:10 pm - 6:00 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 50mnonstop

$504Southwest

Wed, Oct 7 - Sun, Oct 11

10:20 am - 11:05 amMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 45mnonstop

5:55 am - 6:45 amMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 50mnonstop

$504Southwest

Tue, Oct 6 - Thu, Oct 8

Cheap direct flights

Enter your travel dates to find the best prices.

9:10 pm - 10:15 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

1h 05mnonstop

5:30 am - 6:35 amMKE Milwaukee-Mitchell-MDW Chicago Midway

1h 05mnonstop

$209Southwest

Tue, Nov 10 - Thu, Nov 12

9:15 pm - 10:15 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

1h 00mnonstop

6:20 am - 7:20 amMKE Milwaukee-Mitchell-MDW Chicago Midway

1h 00mnonstop

$209Southwest

Thu, Nov 12 - Wed, Nov 18

9:40 pm - 10:35 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 55mnonstop

4:50 pm - 5:40 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 50mnonstop

$209Southwest

Thu, Oct 29 - Thu, Nov 5

9:15 pm - 10:10 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 55mnonstop

6:20 am - 7:20 amMKE Milwaukee-Mitchell-MDW Chicago Midway

1h 00mnonstop

$209Southwest

Mon, Nov 2 - Wed, Nov 4

10:20 am - 11:05 amMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 45mnonstop

4:15 pm - 5:10 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 55mnonstop

$209Southwest

Wed, Oct 28 - Wed, Nov 4

10:40 am - 11:25 amMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 45mnonstop

5:45 am - 6:50 amMKE Milwaukee-Mitchell-MDW Chicago Midway

1h 05mnonstop

$209Southwest

Sat, Oct 31 - Sat, Nov 7

10:10 am - 11:00 amMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 50mnonstop

4:50 pm - 5:40 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 50mnonstop

$229Southwest

Sat, Nov 21 - Sun, Nov 22

9:15 pm - 10:15 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

1h 00mnonstop

5:40 am - 6:45 amMKE Milwaukee-Mitchell-MDW Chicago Midway

1h 05mnonstop

$229Southwest

Sun, Nov 15 - Sat, Nov 21

9:55 am - 10:45 amMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 50mnonstop

5:55 am - 6:45 amMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 50mnonstop

$239Southwest

Thu, Oct 22 - Mon, Oct 26

9:10 pm - 10:15 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

1h 05mnonstop

5:40 am - 6:45 amMKE Milwaukee-Mitchell-MDW Chicago Midway

1h 05mnonstop

$239Southwest

Tue, Nov 10 - Sat, Nov 21

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Southwest flights from Chicago Midway Airport to Wisconsin

Our best Southwest deals on Chicago Midway Airport to Wisconsin flight tickets

Southwest

Oct 28

MDW10:20 amChicago Midway

0h 45m

MKE11:05 amMilwaukee-Mitchell

Nov 4

MKE4:15 pmMilwaukee-Mitchell

0h 55m

MDW5:10 pmChicago Midway

$209

Southwest

Oct 28

MDW10:20 amChicago Midway

0h 45m

MKE11:05 amMilwaukee-Mitchell

Nov 4

MKE8:00 amMilwaukee-Mitchell

4h 05m

1 stop

MDW12:05 pmChicago Midway

$219

Southwest

Oct 28

MDW2:45 pmChicago Midway

8h 00m

2 stops

MKE10:45 pmMilwaukee-Mitchell

Nov 4

MKE6:20 amMilwaukee-Mitchell

1h 00m

MDW7:20 amChicago Midway

$224

Frontier flights from Chicago Midway Airport to Wisconsin

Our best Frontier deals on Chicago Midway Airport to Wisconsin flight tickets

Frontier

Nov 17

MDW6:42 pmChicago Midway

38h 34m

2 stops

MKE9:16 amMilwaukee-Mitchell

Nov 24

MKE6:11 pmMilwaukee-Mitchell

25h 36m

1 stop

MDW7:47 pmChicago Midway

$534

Frontier

Nov 10

MDW12:27 pmChicago Midway

44h 49m

2 stops

MKE9:16 amMilwaukee-Mitchell

Nov 21

MKE6:11 pmMilwaukee-Mitchell

25h 36m

1 stop

MDW7:47 pmChicago Midway

$607

Frontier

Nov 19

MDW6:42 pmChicago Midway

22h 44m

2 stops

MKE5:26 pmMilwaukee-Mitchell

Nov 30

MKE6:11 pmMilwaukee-Mitchell

17h 22m

2 stops

MDW11:33 amChicago Midway

$741

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMilwaukee

MDW Chicago Midway - MKE Milwaukee-Mitchell

MDWMKE

Chicago Midway

Tue 11/10

9:10 pm-10:15 pm

Nonstop1h 05m

Milwaukee-Mitchell

Thu 11/12

5:30 am-6:35 am

Nonstop1h 05m

$209

ChicagoMilwaukee

MDW Chicago Midway - MKE Milwaukee-Mitchell

MDWMKE

Chicago Midway

Thu 11/12

9:15 pm-10:15 pm

Nonstop1h 00m

Milwaukee-Mitchell

Wed 11/18

6:20 am-7:20 am

Nonstop1h 00m

$209

ChicagoMilwaukee

MDW Chicago Midway - MKE Milwaukee-Mitchell

MDWMKE

Chicago Midway

Thu 10/29

9:40 pm-10:35 pm

Nonstop0h 55m

Milwaukee-Mitchell

Thu 11/5

4:50 pm-5:40 pm

Nonstop0h 50m

$209

ChicagoMilwaukee

MDW Chicago Midway - MKE Milwaukee-Mitchell

MDWMKE

Chicago Midway

Mon 11/2

9:15 pm-10:10 pm

Nonstop0h 55m

Milwaukee-Mitchell

Wed 11/4

6:20 am-7:20 am

Nonstop1h 00m

$209

Quickest round-trip

ChicagoMilwaukee

MDW Chicago Midway - MKE Milwaukee-Mitchell

MDWMKE

Chicago Midway

Wed 10/28

10:20 am-11:05 am

Nonstop0h 45m

Milwaukee-Mitchell

Wed 11/4

4:15 pm-5:10 pm

Nonstop0h 55m

$209

ChicagoMilwaukee

MDW Chicago Midway - MKE Milwaukee-Mitchell

MDWMKE

Chicago Midway

Sat 10/31

10:40 am-11:25 am

Nonstop0h 45m

Milwaukee-Mitchell

Sat 11/7

5:45 am-6:50 am

Nonstop1h 05m

$209

ChicagoMilwaukee

MDW Chicago Midway - MKE Milwaukee-Mitchell

MDWMKE

Chicago Midway

Sat 10/31

6:05 am-11:15 am

1 stop5h 10m

Milwaukee-Mitchell

Sat 11/7

1:45 pm-2:40 pm

Nonstop0h 55m

$219

ChicagoMilwaukee

MDW Chicago Midway - MKE Milwaukee-Mitchell

MDWMKE

Chicago Midway

Wed 10/28

10:20 am-11:05 am

Nonstop0h 45m

Milwaukee-Mitchell

Wed 11/4

8:00 am-12:05 pm

1 stop4h 05m

$219

ChicagoMilwaukee

MDW Chicago Midway - MKE Milwaukee-Mitchell

MDWMKE

Chicago Midway

Mon 11/2

6:30 pm-11:55 pm

1 stop5h 25m

Milwaukee-Mitchell

Wed 11/4

6:20 am-7:20 am

Nonstop1h 00m

$219

ChicagoMilwaukee

MDW Chicago Midway - MKE Milwaukee-Mitchell

MDWMKE

Chicago Midway

Tue 11/10

10:05 am-3:15 pm

1 stop5h 10m

Milwaukee-Mitchell

Thu 11/12

4:50 pm-5:40 pm

Nonstop0h 50m

$219

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago Midway Airport to Wisconsin

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

Prices

Airlines

Other information

What is the cheapest day to depart on your flight to Wisconsin?

The cheapest day to depart from Chicago Midway Airport to Wisconsin is on a Saturday. Travelers who choose to depart for Wisconsin on a Saturday will often find tickets for as low as $447. The most expensive day to fly to Wisconsin is Thursday, with ticket prices averaging around $557.

What is the cheapest time of day to depart on your flight to Wisconsin?

Our most recent data shows that the best time of day to fly to Wisconsin is in the morning. Flights from Chicago Midway Airport to Wisconsin during this time can be as low as $398. Flights in the evening are often more expensive with an average ticket price of $557.

What is the cheapest Chicago Midway to Wisconsin flight route?

Fly from Chicago Midway to Milwaukee-Mitchell for the best Chicago Midway - Wisconsin flight prices

What cabin class options are available on Chicago Midway Airport to Wisconsin flights?

There is only 1 cabin class available to choose from on Chicago Midway Airport to Wisconsin 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 Chicago Midway Airport to Wisconsin flights?

You could potentially save up to 57% on your flight if you consider stops on a Chicago Midway Airport to Wisconsin flight.

Cheap Chicago Midway Airport to Wisconsin flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Wisconsin

Best Price Found	$105
Fastest flight time	0h 50m
Direct flights	Every day
Airports in Wisconsin	80 airports

The best one-way flight to Wisconsin from Chicago Midway Airport in the past 72 hours is $105. The best round-trip flight deal from Chicago Midway Airport to Wisconsin found on momondo in the last 72 hours is $209.

The fastest flight from Chicago Midway Airport to Wisconsin takes 0h 50m

Direct flights go from Chicago Midway Airport to Wisconsin every day.

There are 80 airports in Wisconsin. From Chicago Midway Airport there are direct flights to Milwaukee-Mitchell (MKE).

Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Wisconsin

When did momondo last update prices for flights from Chicago Midway Airport to Wisconsin?
Prices for flights from Chicago Midway Airport to Wisconsin are refreshed on a daily basis.
How old do you have to be to fly from Chicago Midway Airport to Wisconsin?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Wisconsin.
What documentation or ID do you need to fly to Wisconsin?
The travel and health documents required for your trip to Wisconsin can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Wisconsin. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago Midway Airport to Wisconsin?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago Midway Airport to Wisconsin is Airbus A320-100/200 (13.51% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (10.81%), Airbus A321-100/200 (8.11%), and Airbus A321neo (8.11%).

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Wisconsin?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Wisconsin. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Wisconsin with flexible booking policies on momondo?

momondo does allow users to show only those flights to Wisconsin from Chicago which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Chicago to Wisconsin?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Wisconsin.

I’m not ready to book a flight from Chicago to Wisconsin right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Wisconsin now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Wisconsin and let you know when they change.