How many flights depart from Milwaukee to Chicago Midway Airport on average per day?

As of September 2026, 1 flights take off from Milwaukee and land in Chicago Midway Airport each day. The most common flight departure time for this route is 5:00AM, with 50% of daily flights taking off in the morning.

How often are flights from Milwaukee to Chicago delayed?

Historically, on average around 23% of flights between Milwaukee and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 100 minutes.

What day of the week experiences the fewest flight delays on this route?

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Thursday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Milwaukee to Chicago flights?

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 24% of their flights experiencing any sort of delay.

What is the cheapest airline that flies from Milwaukee-Mitchell to Chicago Midway?

Southwest is the most popular carrier operating from Milwaukee-Mitchell to Chicago Midway

How many flights depart from Milwaukee to Chicago Midway Airport on average per week?

9 flights are operational weekly from Milwaukee to Chicago Midway Airport as of September 2026. The most popular departure day for this route is Mon, with 22% of flights per week taking off on this day.

What is the most punctual flight time for Milwaukee to Chicago flights?

Generally, flights departing at night tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

When did momondo last update prices for flights from Milwaukee-Mitchell Airport to Chicago Midway Airport?

Prices for flights from Milwaukee-Mitchell Airport to Chicago Midway Airport are updated daily.

How old do you have to be to fly from Milwaukee-Mitchell Airport 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 Milwaukee-Mitchell Airport to Chicago Midway Airport.

What documentation or ID do you need to fly to Chicago Midway Airport?

The travel and health documents required for your trip to Chicago Midway Airport 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 Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$97 Cheap Flights from Milwaukee to Chicago Midway Airport in 2026

Find the cheapest flights from Milwaukee to Chicago

Round-trip

One-way

Last minute

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Cheap round-trip flights

Enter your travel dates to find the best prices.

4:20 pm - 5:10 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 50mnonstop

8:40 pm - 9:25 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 45mnonstop

$193Southwest

Thu, Sep 24 - Mon, Sep 28

8:00 am - 12:15 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

4h 15m1 stop Lambert-St Louis

8:40 pm - 9:25 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 45mnonstop

$203Southwest

Thu, Sep 24 - Mon, Sep 28

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

0h 50mnonstop

2:45 pm - 10:45 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

8h 00m2 stops Lambert-St Louis Nashville Intl

$208Southwest

Mon, Oct 26 - Tue, Oct 27

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

0h 50mnonstop

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

0h 50mnonstop

$211Southwest

Sun, Oct 11 - Wed, Oct 14

8:15 am - 11:55 amMKE Milwaukee-Mitchell-MDW Chicago Midway

3h 40m1 stop Lambert-St Louis

4:30 pm - 10:25 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

5h 55m1 stop Lambert-St Louis

$213Southwest

Thu, Oct 1 - Wed, Oct 7

8:15 am - 12:00 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

3h 45m1 stop Lambert-St Louis

2:45 pm - 10:45 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

8h 00m2 stops Lambert-St Louis Nashville Intl

$218Southwest

Mon, Oct 26 - Tue, Oct 27

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

0h 50mnonstop

9:25 am - 3:25 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

6h 00m1 stop Kansas City

$221Southwest

Sun, Oct 11 - Wed, Oct 14

5:50 pm - 10:40 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

4h 50m1 stop Lambert-St Louis

6:30 pm - 11:05 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

4h 35m1 stop Lambert-St Louis

$223Southwest

Fri, Nov 6 - Mon, Nov 9

5:45 am - 6:30 amMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 45mnonstop

6:15 pm - 7:10 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 55mnonstop

$229Southwest

Thu, Sep 24 - Sun, Sep 27

4:50 pm - 10:00 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

5h 10m1 stop Lambert-St Louis

6:15 pm - 7:10 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 55mnonstop

$239Southwest

Thu, Sep 24 - Sun, Sep 27

Cheap last minute flights

Enter your travel dates to find the best prices.

6:40 am - 7:30 amMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 50mnonstop

8:35 pm - 9:20 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 45mnonstop

$303Southwest

Wed, Sep 9 - Wed, Sep 16

3:40 pm - 4:30 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 50mnonstop

2:00 pm - 8:00 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

6h 00m1 stop Lambert-St Louis

$313Southwest

Wed, Sep 9 - Wed, Sep 16

4:25 pm - 9:55 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

5h 30m1 stop Lambert-St Louis

4:40 pm - 8:00 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

3h 20m1 stop Lambert-St Louis

$323Southwest

Wed, Sep 9 - Wed, Sep 16

5:45 am - 6:30 amMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 45mnonstop

10:15 am - 11:05 amMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 50mnonstop

$394Southwest

Sat, Sep 5 - Sat, Sep 12

1:00 pm - 7:20 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

6h 20m1 stop Nashville Intl

6:10 pm - 7:05 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 55mnonstop

$404Southwest

Sat, Sep 5 - Sat, Sep 12

4:20 pm - 5:10 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 50mnonstop

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

0h 45mnonstop

$409Southwest

Thu, Sep 10 - Sun, Sep 13

1:00 pm - 7:20 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

6h 20m1 stop Nashville Intl

9:55 am - 3:45 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

5h 50m1 stop Lambert-St Louis

$414Southwest

Sat, Sep 5 - Sat, Sep 12

4:20 pm - 5:10 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 50mnonstop

5:50 pm - 9:55 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

4h 05m1 stop Lambert-St Louis

$419Southwest

Thu, Sep 10 - Sun, Sep 13

8:00 am - 12:15 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

4h 15m1 stop Lambert-St Louis

7:35 am - 11:50 amMDW Chicago Midway-MKE Milwaukee-Mitchell

4h 15m1 stop Nashville Intl

$429Southwest

Thu, Sep 10 - Sun, Sep 13

3:10 pm - 4:00 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 50mnonstop

8:35 pm - 9:20 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 45mnonstop

$469Southwest

Tue, Sep 8 - Tue, Sep 8

Cheap direct flights

Enter your travel dates to find the best prices.

4:20 pm - 5:10 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 50mnonstop

8:40 pm - 9:25 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 45mnonstop

$193Southwest

Thu, Sep 24 - Mon, Sep 28

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

1h 05mnonstop

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

0h 50mnonstop

$203Southwest

Fri, Nov 6 - Mon, Nov 9

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

0h 50mnonstop

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

0h 50mnonstop

$211Southwest

Sun, Oct 11 - Wed, Oct 14

5:45 am - 6:30 amMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 45mnonstop

6:15 pm - 7:10 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 55mnonstop

$229Southwest

Thu, Sep 24 - Sun, Sep 27

5:45 am - 6:30 amMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 45mnonstop

10:15 am - 11:05 amMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 50mnonstop

$258Southwest

Sat, Sep 19 - Wed, Sep 23

3:10 pm - 4:00 pmMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 50mnonstop

10:15 am - 11:05 amMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 50mnonstop

$287Southwest

Tue, Sep 15 - Sat, Sep 19

6:40 am - 7:30 amMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 50mnonstop

10:15 am - 11:05 amMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 50mnonstop

$299Southwest

Tue, Sep 22 - Tue, Sep 22

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

0h 50mnonstop

7:15 pm - 8:05 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 50mnonstop

$300Southwest

Wed, Oct 7 - Sat, Oct 10

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

0h 55mnonstop

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

0h 50mnonstop

$338Southwest

Thu, Dec 24 - Sat, Jan 2

6:40 am - 7:30 amMKE Milwaukee-Mitchell-MDW Chicago Midway

0h 50mnonstop

8:35 pm - 9:20 pmMDW Chicago Midway-MKE Milwaukee-Mitchell

0h 45mnonstop

$378Southwest

Wed, Sep 16 - Tue, Sep 22

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Southwest flights from Milwaukee to Chicago Midway Airport

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

Southwest

Sep 24

MKE4:20 pmMilwaukee-Mitchell

0h 50m

MDW5:10 pmChicago Midway

Sep 28

MDW8:40 pmChicago Midway

0h 45m

MKE9:25 pmMilwaukee-Mitchell

$193

Southwest

Sep 24

MKE8:00 amMilwaukee-Mitchell

4h 15m

1 stop

MDW12:15 pmChicago Midway

Sep 28

MDW8:40 pmChicago Midway

0h 45m

MKE9:25 pmMilwaukee-Mitchell

$203

Southwest

Oct 26

MKE5:55 amMilwaukee-Mitchell

0h 50m

MDW6:45 amChicago Midway

Oct 27

MDW2:45 pmChicago Midway

8h 00m

2 stops

MKE10:45 pmMilwaukee-Mitchell

$208

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

MilwaukeeChicago

MKE Milwaukee-Mitchell - MDW Chicago Midway

MKEMDW

Milwaukee-Mitchell

Thu 9/24

4:20 pm-5:10 pm

Nonstop0h 50m

Chicago Midway

Mon 9/28

8:40 pm-9:25 pm

Nonstop0h 45m

$193

MilwaukeeChicago

MKE Milwaukee-Mitchell - MDW Chicago Midway

MKEMDW

Milwaukee-Mitchell

Thu 9/24

8:00 am-12:15 pm

1 stop4h 15m

Chicago Midway

Mon 9/28

8:40 pm-9:25 pm

Nonstop0h 45m

$203

MilwaukeeChicago

MKE Milwaukee-Mitchell - MDW Chicago Midway

MKEMDW

Milwaukee-Mitchell

Mon 10/26

5:55 am-6:45 am

Nonstop0h 50m

Chicago Midway

Tue 10/27

2:45 pm-10:45 pm

2 stops8h 00m

$208

MilwaukeeChicago

MKE Milwaukee-Mitchell - MDW Chicago Midway

MKEMDW

Milwaukee-Mitchell

Sun 10/11

5:55 am-6:45 am

Nonstop0h 50m

Chicago Midway

Wed 10/14

8:45 pm-9:35 pm

Nonstop0h 50m

$211

MilwaukeeChicago

MKE Milwaukee-Mitchell - MDW Chicago Midway

MKEMDW

Milwaukee-Mitchell

Thu 10/1

8:15 am-11:55 am

1 stop3h 40m

Chicago Midway

Wed 10/7

4:30 pm-10:25 pm

1 stop5h 55m

$213

MilwaukeeChicago

MKE Milwaukee-Mitchell - MDW Chicago Midway

MKEMDW

Milwaukee-Mitchell

Mon 10/26

8:15 am-12:00 pm

1 stop3h 45m

Chicago Midway

Tue 10/27

2:45 pm-10:45 pm

2 stops8h 00m

$218

MilwaukeeChicago

MKE Milwaukee-Mitchell - MDW Chicago Midway

MKEMDW

Milwaukee-Mitchell

Sun 10/11

5:10 pm-6:00 pm

Nonstop0h 50m

Chicago Midway

Wed 10/14

9:25 am-3:25 pm

1 stop6h 00m

$221

MilwaukeeChicago

MKE Milwaukee-Mitchell - MDW Chicago Midway

MKEMDW

Milwaukee-Mitchell

Fri 11/6

5:50 pm-10:40 pm

1 stop4h 50m

Chicago Midway

Mon 11/9

6:30 pm-11:05 pm

1 stop4h 35m

$223

MilwaukeeChicago

MKE Milwaukee-Mitchell - MDW Chicago Midway

MKEMDW

Milwaukee-Mitchell

Thu 9/24

5:45 am-6:30 am

Nonstop0h 45m

Chicago Midway

Sun 9/27

6:15 pm-7:10 pm

Nonstop0h 55m

$229

MilwaukeeChicago

MKE Milwaukee-Mitchell - MDW Chicago Midway

MKEMDW

Milwaukee-Mitchell

Thu 9/24

4:50 pm-10:00 pm

1 stop5h 10m

Chicago Midway

Sun 9/27

6:15 pm-7:10 pm

Nonstop0h 55m

$239

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 Milwaukee 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

Prices

Airlines

Delays

Other information

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 Milwaukee. The lowest ticket price found for a Saturday departure recently was $403. 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, Tuesday is the most expensive day to depart from Milwaukee because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $453.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Milwaukee 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 $422. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Milwaukee-Mitchell to Chicago Midway flight route?

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

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

There is only 1 cabin class available to choose from on Milwaukee 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.

When to book flights from Milwaukee to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Milwaukee to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Milwaukee to Chicago Midway Airport (MKE to MDW) flight deals and tips

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

Best Price Found	$97
Fastest flight time	0h 50m
Direct flights	Every day

The best one-way flight to Chicago Midway Airport from Milwaukee in the past 72 hours is $97. The best round-trip flight deal from Milwaukee to Chicago Midway Airport found on momondo in the last 72 hours is $193.

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

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

Search flight deals

Frequently asked questions about flying from Milwaukee to Chicago Midway Airport

How far is Milwaukee-Mitchell to Chicago Midway by plane?
A flight from Milwaukee-Mitchell to Chicago Midway will travel around 86.8 mi. In terms of flight time, this usually takes a little over 0h 50m.
When did momondo last update prices for flights from Milwaukee-Mitchell Airport to Chicago Midway Airport?
Prices for flights from Milwaukee-Mitchell Airport to Chicago Midway Airport are updated daily.
How old do you have to be to fly from Milwaukee-Mitchell Airport 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 Milwaukee-Mitchell Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway Airport 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 Chicago Midway Airport. 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 Milwaukee to Chicago Midway Airport?
Based on momondo bookings for flights between Milwaukee and Chicago Midway Airport, the leading plane model is Embraer 175 (Enhanced Winglets), making up 9.66% of the total bookings. Other popular models include Airbus A321-100/200 with 8.70%, Boeing 737-800 with 8.21%, and Canadair (Bombardier) Regional Jet 900 with 7.73%.

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

Finding the right flight to Chicago from Milwaukee 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 Milwaukee to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Milwaukee with this policy.

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

Once all potential Milwaukee to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Yes momondo offers price alerts on flights to Chicago from Milwaukee. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Cheap flights from Milwaukee to Chicago from $97

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Milwaukee to Chicago departing on 10/1. 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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Southwest flights from Milwaukee to Chicago Midway Airport

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

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

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

What is the cheapest day to depart on your flight to Chicago Midway Airport?

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

What is the cheapest Milwaukee-Mitchell to Chicago Midway flight route?

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

What is the cheapest airline that flies from Milwaukee-Mitchell to Chicago Midway?

How often are flights from Milwaukee to Chicago delayed?

What is the most punctual flight time for Milwaukee to Chicago flights?

What day of the week experiences the fewest flight delays on this route?

Which airline has the best punctuality record on Milwaukee to Chicago flights?

How many flights depart from Milwaukee to Chicago Midway Airport on average per day?

How many flights depart from Milwaukee to Chicago Midway Airport on average per week?

When to book flights from Milwaukee to Chicago Midway Airport

Cheap Milwaukee to Chicago Midway Airport (MKE to MDW) flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Frequently asked questions about flying from Milwaukee to Chicago Midway Airport

Traveling to a place near Chicago?

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An easier way to manage your Chicago Midway Airport trip

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List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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