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.

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

According to our data, SkyWest Airlines have had the least number of delays on this route over the last 12 months; with about 11% of their flights experiencing any sort of delay.

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. Sunday has historically seen more delays on average compared to the rest of the week.

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

As of March 2026, 41 flights take off from Milwaukee and land in Chicago each day. The most common flight departure time for this route is 8:00AM, with 61% of daily flights taking off at noon.

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

As of March 2026, 293 flights take off from Milwaukee and land in Chicago each week. The most common flight departure day for this route is Sun, with 18% of weekly flights taking off on this day.

How often are flights from Milwaukee to Chicago delayed?

Historically, on average around 13% 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 121 minutes.

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

Southwest and United Airlines are the most popular carriers operating from Milwaukee-Mitchell to Chicago

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

Prices for flights from Milwaukee-Mitchell Airport to Chicago are refreshed on a daily basis.

How many operators does momondo search for flights from Milwaukee-Mitchell Airport to Chicago?

As of March 2026, there are 2 operators available to choose from for flights from Milwaukee-Mitchell Airport to Chicago.

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

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 Milwaukee-Mitchell Airport to Chicago.

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

The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$50 Cheap Flights from Milwaukee to Chicago in 2026

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Find the cheapest flights from Milwaukee to Chicago

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

12:13 pm - 1:22 pm

MKE

ORD

1h 09mnonstop

8:57 pm - 10:03 pm

ORD

MKE

1h 06mnonstop

$117United Airlines

Wed, Apr 29 - Sat, May 2

5:41 pm - 7:02 pm

MKE

ORD

1h 21mnonstop

7:01 pm - 8:06 pm

ORD

MKE

1h 05mnonstop

$118American Airlines

Mon, Apr 13 - Mon, Apr 20

6:50 am - 7:59 am

MKE

ORD

1h 09mnonstop

10:45 pm - 11:43 pm

ORD

MKE

0h 58mnonstop

$158United Airlines

Thu, Apr 16 - Sun, Apr 19

8:49 am - 10:00 am

MKE

ORD

1h 11mnonstop

7:06 am - 8:01 am

ORD

MKE

0h 55mnonstop

$162American Airlines

Mon, Mar 16 - Sat, Mar 21

7:01 am - 8:20 am

MKE

ORD

1h 19mnonstop

4:55 pm - 6:00 pm

ORD

MKE

1h 05mnonstop

$166American Airlines

Thu, Apr 9 - Mon, Apr 13

6:00 am - 7:03 am

MKE

ORD

1h 03mnonstop

7:45 pm - 8:48 pm

ORD

MKE

1h 03mnonstop

$177United Airlines

Sat, Mar 28 - Sat, Apr 4

5:41 pm - 7:02 pm

MKE

ORD

1h 21mnonstop

6:40 am - 7:41 am

ORD

MKE

1h 01mnonstop

$182American Airlines

Thu, Apr 16 - Sun, Apr 19

5:50 am - 6:50 am

MKE

MDW

1h 00mnonstop

11:00 am - 11:45 am

MDW

MKE

0h 45mnonstop

$187Southwest

Fri, Mar 27 - Tue, Mar 31

5:50 am - 6:50 am

MKE

MDW

1h 00mnonstop

9:10 pm - 9:55 pm

MDW

MKE

0h 45mnonstop

$207Southwest

Fri, Mar 13 - Tue, Mar 17

4:50 pm - 5:40 pm

MKE

MDW

0h 50mnonstop

9:30 pm - 10:15 pm

MDW

MKE

0h 45mnonstop

$208Southwest

Mon, Apr 13 - Mon, Apr 20

United Airlines flights from Milwaukee to Chicago

Our best United Airlines deals on Milwaukee to Chicago flight tickets

United Airlines

Apr 29

MKE12:13 pmMilwaukee-Mitchell

1h 09m

ORD1:22 pmChicago O'Hare Intl

May 2

ORD8:57 pmChicago O'Hare Intl

1h 06m

MKE10:03 pmMilwaukee-Mitchell

$117

United Airlines

Apr 16

MKE6:50 amMilwaukee-Mitchell

1h 09m

ORD7:59 amChicago O'Hare Intl

Apr 19

ORD10:45 pmChicago O'Hare Intl

0h 58m

MKE11:43 pmMilwaukee-Mitchell

$158

United Airlines

Mar 28

MKE6:00 amMilwaukee-Mitchell

1h 03m

ORD7:03 amChicago O'Hare Intl

Apr 4

ORD7:45 pmChicago O'Hare Intl

1h 03m

MKE8:48 pmMilwaukee-Mitchell

$177

American Airlines flights from Milwaukee to Chicago

Our best American Airlines deals on Milwaukee to Chicago flight tickets

American Airlines

Apr 13

MKE5:41 pmMilwaukee-Mitchell

1h 21m

ORD7:02 pmChicago O'Hare Intl

Apr 20

ORD7:01 pmChicago O'Hare Intl

1h 05m

MKE8:06 pmMilwaukee-Mitchell

$118

American Airlines

Mar 16

MKE8:49 amMilwaukee-Mitchell

1h 11m

ORD10:00 amChicago O'Hare Intl

Mar 21

ORD7:06 amChicago O'Hare Intl

0h 55m

MKE8:01 amMilwaukee-Mitchell

$162

American Airlines

Apr 9

MKE7:01 amMilwaukee-Mitchell

1h 19m

ORD8:20 amChicago O'Hare Intl

Apr 13

ORD4:55 pmChicago O'Hare Intl

1h 05m

MKE6:00 pmMilwaukee-Mitchell

$166

Fly from

Fly to

Route

Depart

Return

Price

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Wed 4/29

12:13 pm-1:22 pm

Nonstop1h 09m

Chicago O'Hare Intl

Sat 5/2

8:57 pm-10:03 pm

Nonstop1h 06m

$117

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Mon 4/13

5:41 pm-7:02 pm

Nonstop1h 21m

Chicago O'Hare Intl

Mon 4/20

7:01 pm-8:06 pm

Nonstop1h 05m

$118

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Thu 4/16

6:50 am-7:59 am

Nonstop1h 09m

Chicago O'Hare Intl

Sun 4/19

10:45 pm-11:43 pm

Nonstop0h 58m

$158

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Mon 3/16

8:49 am-10:00 am

Nonstop1h 11m

Chicago O'Hare Intl

Sat 3/21

7:06 am-8:01 am

Nonstop0h 55m

$162

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Thu 4/9

7:01 am-8:20 am

Nonstop1h 19m

Chicago O'Hare Intl

Mon 4/13

4:55 pm-6:00 pm

Nonstop1h 05m

$166

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Sat 3/28

6:00 am-7:03 am

Nonstop1h 03m

Chicago O'Hare Intl

Sat 4/4

7:45 pm-8:48 pm

Nonstop1h 03m

$177

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Thu 4/16

5:41 pm-7:02 pm

Nonstop1h 21m

Chicago O'Hare Intl

Sun 4/19

6:40 am-7:41 am

Nonstop1h 01m

$182

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Fri 3/27

5:50 am-6:50 am

Nonstop1h 00m

Chicago Midway

Tue 3/31

11:00 am-11:45 am

Nonstop0h 45m

$187

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Fri 3/13

5:50 am-6:50 am

Nonstop1h 00m

Chicago Midway

Tue 3/17

9:10 pm-9:55 pm

Nonstop0h 45m

$207

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Mon 4/13

4:50 pm-5:40 pm

Nonstop0h 50m

Chicago Midway

Mon 4/20

9:30 pm-10:15 pm

Nonstop0h 45m

$208

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

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?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $443. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Milwaukee to Chicago for around $546.

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

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Milwaukee to Chicago during this time can be as low as $446. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $702.

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

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

What cabin class options are available on Milwaukee-Mitchell to Chicago flights?

There are 4 cabin classes available to choose from on Milwaukee-Mitchell to Chicago 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

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

Estimated round-trip price

Cheap Milwaukee to Chicago (MKE to CHI) flight deals and tips

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

Best Price Found	$178
Fastest flight time	0h 50m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Milwaukee in the past 72 hours is $178. The best round-trip flight deal from Milwaukee to Chicago found on momondo in the last 72 hours is $328.

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

Direct flights go from Milwaukee to Chicago every day.

There are 3 airports in Chicago. From Milwaukee there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).

Search flight deals

How far is Milwaukee-Mitchell to Chicago by plane?
A flight from Milwaukee-Mitchell to Chicago will travel around 81.6 mi. By plane, this route typically takes 0h 50m.
When did momondo last update prices for flights from Milwaukee-Mitchell Airport to Chicago?
Prices for flights from Milwaukee-Mitchell Airport to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from Milwaukee-Mitchell Airport to Chicago?
As of March 2026, there are 2 operators available to choose from for flights from Milwaukee-Mitchell Airport to Chicago.
How old do you have to be to fly from Milwaukee-Mitchell Airport to Chicago?
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 Milwaukee-Mitchell Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Milwaukee to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Milwaukee to Chicago is Boeing 737 MAX 8 (16.49% of total bookings). The next most popular plane models are Boeing 737-800 Passenger/BBJ2 (winglets) (11.92%), Embraer 175 (Enhanced Winglets) (6.81%), and Boeing 737-800 (6.40%).
What is the most popular airline from Milwaukee to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Milwaukee to Chicago is American Airlines (100% of total bookings).

Best airlines flying from Milwaukee to Chicago

Compare and see reviews for airlines that fly from Milwaukee to Chicago with momondo

Airline	Rating	Free Cancellation	Price
American Airlines	PriceFrom $179	Free Cancellation	Rating 7.1 11,370 reviews		Search American Airlines flights
United Airlines	PriceFrom $179	Free Cancellation	Rating 7.4 9,370 reviews		Search United Airlines flights

United Airlines Flights From Milwaukee to Chicago
The lowest priced United Airlines flight from Milwaukee to Chicago from the last 72 hours was $179. Generally, United Airlines has 44 flights on this route every week with an average price of $239. United Airlines is rated 7.4/10 by our users.
American Airlines Flights From Milwaukee to Chicago
$179 is the best American Airlines flight deal from Milwaukee to Chicago found on momondo over the last 72 hours. The average American Airlines ticket price found was closer to $179, however, with flight time and availability significantly affecting the price. American Airlines (7.1/10 from 11,370 user reviews) flies into Chicago from Milwaukee 34 times in an average week so prices can vary.

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Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Milwaukee to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

Yes. All flights to Chicago from Milwaukee on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Milwaukee.

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

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

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Cheap flights from Milwaukee to Chicago from $50

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 4/11. 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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How to get the cheapest flight ticket from Milwaukee to Chicago

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

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

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

What cabin class options are available on Milwaukee-Mitchell to Chicago flights?

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

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 on average per day?

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

When to book flights from Milwaukee to Chicago

Cheap Milwaukee to Chicago (MKE to CHI) flight deals and tips

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

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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago

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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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