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 early afternoon have, in the past, seen delays more frequently in comparison.

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

As of January 2026, 42 flights take off from Milwaukee and land in Chicago each day. The most common flight departure time for this route is 7:00AM, with 54% of daily flights taking off at noon.

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

Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Friday 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, Braathens Regional Aviation have had the least number of delays on this route over the last 12 months; with about 9% of their flights experiencing any sort of delay.

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

As of January 2026, 299 flights take off from Milwaukee and land in Chicago each week. The most common flight departure day for this route is Tue, with 15% of weekly flights taking off on this day.

How often are flights from Milwaukee to Chicago delayed?

Historically, on average around 11% 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 116 minutes.

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

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

Is flying the fastest way to get from Milwaukee to Chicago?

Between booking a train from Milwaukee to Chicago versus opting for a bus from Milwaukee to Chicago or a flight from Milwaukee to Chicago you can expect relatively similar travel times.

Is flying the cheapest way to get from Milwaukee to Chicago?

Expect a train to be one of the cheapest options available to you for travel. Currently, a train has deals available from $42. While they may not be the most cost-effective options currently available a flight from Milwaukee to Chicago or a bus from Milwaukee to Chicago can also be options worth looking into if other factors outside of cost are a higher priority.

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 January 2026, there is 1 operator 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.

$89 Cheap Flights from Milwaukee to Chicago in 2026

Q: What is the typical price of a round-trip flight between Milwaukee and Chicago?

Prices are currently low for flights on this route. Typical prices usually range from $270 to $452. The lowest price recently found on this route was $177.

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

3:20 pm - 4:33 pm

MKE

ORD

1h 13mnonstop

5:45 pm - 6:43 pm

ORD

MKE

0h 58mnonstop

$177United Airlines

mar., feb. 10 - mar., feb. 17

9:23 am - 10:32 am

MKE

ORD

1h 09mnonstop

8:56 am - 9:49 am

ORD

MKE

0h 53mnonstop

$188United Airlines

dom., may. 17 - sáb., may. 30

2:46 pm - 4:02 pm

MKE

ORD

1h 16mnonstop

8:06 am - 9:03 am

ORD

MKE

0h 57mnonstop

$192American Airlines

dom., feb. 1 - dom., feb. 8

6:10 am - 7:29 am

MKE

ORD

1h 19mnonstop

10:00 pm - 10:57 pm

ORD

MKE

0h 57mnonstop

$197American Airlines

mar., feb. 10 - mar., feb. 17

6:10 am - 7:29 am

MKE

ORD

1h 19mnonstop

8:05 am - 9:00 am

ORD

MKE

0h 55mnonstop

$198American Airlines

jue., feb. 5 - sáb., feb. 14

5:25 am - 10:20 am

MKE

MDW

4h 55m

1 stop

6:10 am - 11:30 am

MDW

MKE

5h 20m

1 stop

$199Southwest

lun., feb. 23 - mié., feb. 25

10:30 am - 11:43 am

MKE

ORD

1h 13mnonstop

9:50 pm - 10:56 pm

ORD

MKE

1h 06mnonstop

$207United Airlines

mar., ene. 27 - vie., ene. 30

3:50 pm - 7:05 pm

MKE

MDW

3h 15m

1 stop

6:00 am - 11:55 am

MDW

MKE

5h 55m

1 stop

$209Southwest

mié., feb. 11 - mié., feb. 18

5:00 am - 6:10 am

MKE

ORD

1h 10mnonstop

11:48 am - 12:44 pm

ORD

MKE

0h 56mnonstop

$216American Airlines

jue., jun. 18 - mar., jun. 23

3:50 pm - 7:05 pm

MKE

MDW

3h 15m

1 stop

11:00 am - 4:20 pm

MDW

MKE

5h 20m

1 stop

$239Southwest

mar., feb. 10 - mar., feb. 17

United Airlines flights from Milwaukee to Chicago

Our best United Airlines deals on Milwaukee to Chicago flight tickets

United Airlines

Feb 10

MKE11:30 amMilwaukee-Mitchell

1h 13m

ORD12:43 pmChicago O'Hare Intl

Feb 17

ORD9:30 pmChicago O'Hare Intl

0h 58m

MKE10:28 pmMilwaukee-Mitchell

$177

United Airlines

May 17

MKE9:23 amMilwaukee-Mitchell

1h 09m

ORD10:32 amChicago O'Hare Intl

May 30

ORD8:56 amChicago O'Hare Intl

0h 53m

MKE9:49 amMilwaukee-Mitchell

$188

United Airlines

Jan 31

MKE2:32 pmMilwaukee-Mitchell

1h 13m

ORD3:45 pmChicago O'Hare Intl

Feb 1

ORD7:42 pmChicago O'Hare Intl

1h 06m

MKE8:48 pmMilwaukee-Mitchell

$207

Frontier flights from Milwaukee to Chicago

Our best Frontier deals on Milwaukee to Chicago flight tickets

Frontier

Feb 11

MKE4:39 pmMilwaukee-Mitchell

18h 07m

1 stop

ORD10:46 amChicago O'Hare Intl

Feb 18

ORD8:30 amChicago O'Hare Intl

23h 10m

1 stop

MKE7:40 amMilwaukee-Mitchell

$316

Frontier

Feb 11

MKE4:39 pmMilwaukee-Mitchell

18h 07m

1 stop

ORD10:46 amChicago O'Hare Intl

Feb 18

ORD6:02 pmChicago O'Hare Intl

13h 38m

2 stops

MKE7:40 amMilwaukee-Mitchell

$343

Frontier

Feb 19

MKE8:39 amMilwaukee-Mitchell

12h 07m

2 stops

ORD8:46 pmChicago O'Hare Intl

Feb 23

ORD3:50 pmChicago O'Hare Intl

23h 54m

1 stop

MKE3:44 pmMilwaukee-Mitchell

$354

Fly from

Fly to

Route

Depart

Return

Price

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

mar. 2/10

3:20 pm-4:33 pm

Nonstop1h 13m

Chicago O'Hare Intl

mar. 2/17

5:45 pm-6:43 pm

Nonstop0h 58m

$177

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

dom. 5/17

9:23 am-10:32 am

Nonstop1h 09m

Chicago O'Hare Intl

sáb. 5/30

8:56 am-9:49 am

Nonstop0h 53m

$188

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

dom. 2/1

2:46 pm-4:02 pm

Nonstop1h 16m

Chicago O'Hare Intl

dom. 2/8

8:06 am-9:03 am

Nonstop0h 57m

$192

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

mar. 2/10

6:10 am-7:29 am

Nonstop1h 19m

Chicago O'Hare Intl

mar. 2/17

10:00 pm-10:57 pm

Nonstop0h 57m

$197

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

jue. 2/5

6:10 am-7:29 am

Nonstop1h 19m

Chicago O'Hare Intl

sáb. 2/14

8:05 am-9:00 am

Nonstop0h 55m

$198

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

lun. 2/23

5:25 am-10:20 am

1 stop4h 55m

Chicago Midway

mié. 2/25

6:10 am-11:30 am

1 stop5h 20m

$199

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

mar. 1/27

10:30 am-11:43 am

Nonstop1h 13m

Chicago O'Hare Intl

vie. 1/30

9:50 pm-10:56 pm

Nonstop1h 06m

$207

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

mié. 2/11

3:50 pm-7:05 pm

1 stop3h 15m

Chicago Midway

mié. 2/18

6:00 am-11:55 am

1 stop5h 55m

$209

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

jue. 6/18

5:00 am-6:10 am

Nonstop1h 10m

Chicago O'Hare Intl

mar. 6/23

11:48 am-12:44 pm

Nonstop0h 56m

$216

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

mar. 2/10

3:50 pm-7:05 pm

1 stop3h 15m

Chicago Midway

mar. 2/17

11:00 am-4:20 pm

1 stop5h 20m

$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

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 typical price of a round-trip flight between Milwaukee and Chicago?

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 $449. 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 $573.

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 $465. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $717.

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

Fly from Milwaukee-Mitchell to Chicago O'Hare Intl 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	$205
Fastest flight time	1h 00m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Milwaukee in the past 72 hours is $205. The best round-trip flight deal from Milwaukee to Chicago found on momondo in the last 72 hours is $341.

The fastest flight from Milwaukee to Chicago takes 1h 00m

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

Is flying the fastest way to get from Milwaukee to Chicago?
Between booking a train from Milwaukee to Chicago versus opting for a bus from Milwaukee to Chicago or a flight from Milwaukee to Chicago you can expect relatively similar travel times.
Is flying the cheapest way to get from Milwaukee to Chicago?
Expect a train to be one of the cheapest options available to you for travel. Currently, a train has deals available from $42. While they may not be the most cost-effective options currently available a flight from Milwaukee to Chicago or a bus from Milwaukee to Chicago can also be options worth looking into if other factors outside of cost are a higher priority.
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 1h 00m.
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 January 2026, there is 1 operator 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 (11.99% of total bookings). The next most popular plane models are Boeing 737-800 Passenger/BBJ2 (winglets) (10.05%), Boeing 737-800 (7.29%), and Embraer 175 (Enhanced Winglets) (7.21%).
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 7.2 11,119 reviews		Search American Airlines flights

American Airlines Flights From Milwaukee to Chicago
The lowest priced American Airlines flight from Milwaukee to Chicago from the last 72 hours was $179. Generally, American Airlines has 23 flights on this route every week with an average price of $239. American Airlines is rated 7.2/10 by our users.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

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 $89

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 2/20. 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 typical price of a round-trip flight between Milwaukee and 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?

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 $465. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $717.

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

Fly from Milwaukee-Mitchell to Chicago O'Hare Intl 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.

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

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

How often are flights from Milwaukee to Chicago delayed?

Historically, on average around 11% 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 116 minutes.

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 early afternoon have, in the past, seen delays more frequently in comparison.

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

Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Friday 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, Braathens Regional Aviation have had the least number of delays on this route over the last 12 months; with about 9% of their flights experiencing any sort of delay.

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

As of January 2026, 42 flights take off from Milwaukee and land in Chicago each day. The most common flight departure time for this route is 7:00AM, with 54% of daily flights taking off at noon.

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

As of January 2026, 299 flights take off from Milwaukee and land in Chicago each week. The most common flight departure day for this route is Tue, with 15% of weekly flights taking off on this day.

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

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Is flying the fastest way to get from Milwaukee to Chicago?

Is flying the cheapest way to get from Milwaukee to Chicago?

How far is Milwaukee-Mitchell to Chicago by plane?

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

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

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

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

What is the most popular plane model from Milwaukee to Chicago?

What is the most popular airline from Milwaukee to Chicago?

Best airlines flying from Milwaukee to Chicago

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

American Airlines Flights From Milwaukee to Chicago

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago