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

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

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

As of September 2025, 35 flights take off from Milwaukee and land in Chicago each day. The most common flight departure time for this route is 10:00AM, with 45% of daily flights taking off at noon.

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

As of September 2025, 246 flights take off from Milwaukee and land in Chicago each week. The most common flight departure day for this route is Mon, with 21% of weekly flights taking off on this day.

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 September 2025, 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.

$109 Cheap Flights from Milwaukee to Chicago in 2025/26

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 $214 to $251. The lowest price recently found on this route was $179.

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Find the cheapest flights from Milwaukee to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

5:45 pm - 6:55 pmMKE-ORD

1h 10mnonstop

4:20 pm - 5:17 pmORD-MKE

0h 57mnonstop

$179United Airlines

Find Deal

Sun, Oct 19 - Sun, Oct 26

5:00 am - 6:10 amMKE-ORD

1h 10mnonstop

5:50 pm - 6:56 pmORD-MKE

1h 06mnonstop

$184United Airlines

Find Deal

Wed, Oct 8 - Fri, Oct 17

5:05 am - 6:07 amMKE-ORD

1h 02mnonstop

9:04 am - 10:04 amORD-MKE

1h 00mnonstop

$199American Airlines

Find Deal

Fri, Oct 3 - Sun, Oct 5

2:18 pm - 3:27 pmMKE-ORD

1h 09mnonstop

6:36 pm - 7:46 pmORD-MKE

1h 10mnonstop

$224American Airlines

Find Deal

Mon, Oct 20 - Mon, Oct 27

12:05 pm - 5:10 pmMKE-MDW

5h 05m1 stop

6:45 pm - 11:25 pmMDW-MKE

4h 40m1 stop

$237Southwest

Find Deal

Tue, Oct 21 - Fri, Oct 24

5:50 am - 6:50 amMKE-MDW

1h 00mnonstop

9:45 pm - 10:30 pmMDW-MKE

0h 45mnonstop

$248Southwest

Find Deal

Tue, Mar 17 - Thu, Mar 19

8:04 pm - 11:53 pmMKE-ORD

27h 49m1 stop

6:50 am - 7:18 pmORD-MKE

12h 28m1 stop

$266Frontier

Find Deal

Mon, Oct 20 - Mon, Oct 27

8:04 pm - 3:39 pmMKE-ORD

19h 35m1 stop

10:18 am - 11:02 amORD-MKE

24h 44m1 stop

$288Multiple Airlines

Find Deal

Mon, Nov 10 - Wed, Nov 12

8:04 pm - 1:47 pmMKE-ORD

17h 43m2 stops

10:51 am - 7:18 pmORD-MKE

8h 27m1 stop

$301Frontier

Find Deal

Mon, Oct 20 - Mon, Oct 27

8:04 pm - 3:39 pmMKE-ORD

19h 35m1 stop

5:59 pm - 11:02 amORD-MKE

17h 03m2 stops

$323Multiple Airlines

Find Deal

Mon, Nov 10 - Wed, Nov 12

United Airlines flights from Milwaukee to Chicago

Our best United Airlines deals on Milwaukee to Chicago flight tickets

United Airlines

Oct 19

MKE5:45 pmMilwaukee-Mitchell

1h 10m

ORD6:55 pmChicago O'Hare Intl

Oct 26

ORD4:20 pmChicago O'Hare Intl

0h 57m

MKE5:17 pmMilwaukee-Mitchell

$179

Find similar

United Airlines

Oct 8

MKE5:00 amMilwaukee-Mitchell

1h 10m

ORD6:10 amChicago O'Hare Intl

Oct 17

ORD5:50 pmChicago O'Hare Intl

1h 06m

MKE6:56 pmMilwaukee-Mitchell

$184

Find similar

United Airlines

Oct 4

MKE10:50 amMilwaukee-Mitchell

1h 10m

ORD12:00 pmChicago O'Hare Intl

Oct 8

ORD9:05 amChicago O'Hare Intl

1h 06m

MKE10:11 amMilwaukee-Mitchell

$189

Find similar

American Airlines flights from Milwaukee to Chicago

Our best American Airlines deals on Milwaukee to Chicago flight tickets

American Airlines

Oct 1

MKE6:19 amMilwaukee-Mitchell

1h 06m

ORD7:25 amChicago O'Hare Intl

Oct 8

ORD9:13 amChicago O'Hare Intl

1h 05m

MKE10:18 amMilwaukee-Mitchell

$199

Find similar

American Airlines

Oct 20

MKE2:18 pmMilwaukee-Mitchell

1h 09m

ORD3:27 pmChicago O'Hare Intl

Oct 27

ORD6:36 pmChicago O'Hare Intl

1h 10m

MKE7:46 pmMilwaukee-Mitchell

$224

Find similar

American Airlines

Oct 21

MKE4:59 pmMilwaukee-Mitchell

1h 11m

ORD6:10 pmChicago O'Hare Intl

Oct 24

ORD7:25 pmChicago O'Hare Intl

1h 00m

MKE8:25 pmMilwaukee-Mitchell

$247

Find similar

Fly from

Fly to

Route

Depart

Return

Price

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Sun 10/19

5:45 pm-6:55 pm

Nonstop1h 10m

Chicago O'Hare Intl

Sun 10/26

4:20 pm-5:17 pm

Nonstop0h 57m

$179

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Wed 10/8

5:00 am-6:10 am

Nonstop1h 10m

Chicago O'Hare Intl

Fri 10/17

5:50 pm-6:56 pm

Nonstop1h 06m

$184

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Fri 10/3

5:05 am-6:07 am

Nonstop1h 02m

Chicago O'Hare Intl

Sun 10/5

9:04 am-10:04 am

Nonstop1h 00m

$199

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Mon 10/20

2:18 pm-3:27 pm

Nonstop1h 09m

Chicago O'Hare Intl

Mon 10/27

6:36 pm-7:46 pm

Nonstop1h 10m

$224

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Tue 10/21

12:05 pm-5:10 pm

1 stop5h 05m

Chicago Midway

Fri 10/24

6:45 pm-11:25 pm

1 stop4h 40m

$237

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Tue 3/17

5:50 am-6:50 am

Nonstop1h 00m

Chicago Midway

Thu 3/19

9:45 pm-10:30 pm

Nonstop0h 45m

$248

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Mon 10/20

8:04 pm-11:53 pm

1 stop27h 49m

Chicago O'Hare Intl

Mon 10/27

6:50 am-7:18 pm

1 stop12h 28m

$266

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Mon 11/10

8:04 pm-3:39 pm

1 stop19h 35m

Chicago O'Hare Intl

Wed 11/12

10:18 am-11:02 am

1 stop24h 44m

$288

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Mon 10/20

8:04 pm-1:47 pm

2 stops17h 43m

Chicago O'Hare Intl

Mon 10/27

10:51 am-7:18 pm

1 stop8h 27m

$301

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Mon 11/10

8:04 pm-3:39 pm

1 stop19h 35m

Chicago O'Hare Intl

Wed 11/12

5:59 pm-11:02 am

2 stops17h 03m

$323

Flights are sorted by cheapest round-trip flights first.

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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

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 $460. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Milwaukee to Chicago for around $571.

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 $481. 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	$160
Fastest flight time	0h 50m
Direct flights	Mon, Tue, Wed, Thu, Sat and Sun
Airports in Chicago	2 airports

The best one-way flight to Chicago from Milwaukee in the past 72 hours is $160. The best round-trip flight deal from Milwaukee to Chicago found on momondo in the last 72 hours is $316.

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

Direct flights go from Milwaukee to Chicago on Monday, Tuesday, Wednesday, Thursday, Saturday and Sunday. There are no airlines offering direct flights.

There are 2 airports near Chicago: 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 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 September 2025, 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 737-800 Passenger/BBJ2 (winglets) (7.98% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (7.28%), Boeing 737 MAX 8 (6.51%), and Boeing 737-800 (5.27%).
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 10,000 reviews		Search American Airlines flights
United Airlines	PriceFrom $229	Free Cancellation	Rating 7.4 8,926 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 $229. Generally, United Airlines has 39 flights on this route every week with an average price of $309. 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 $264, however, with flight time and availability significantly affecting the price. American Airlines (7.2/10 from 10,000 user reviews) flies into Chicago from Milwaukee 23 times in an average week so prices can vary.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

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 $109

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 11/26. 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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Big names and deals

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Filter for what you want

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Find the cheapest flights from Milwaukee to Chicago

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United Airlines flights from Milwaukee to Chicago

Our best United Airlines deals on Milwaukee to Chicago flight tickets

American Airlines flights from Milwaukee to Chicago

Our best American Airlines deals on Milwaukee to Chicago flight tickets

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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

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 $481. 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?

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

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

As of September 2025, 35 flights take off from Milwaukee and land in Chicago each day. The most common flight departure time for this route is 10:00AM, with 45% of daily flights taking off at noon.

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

As of September 2025, 246 flights take off from Milwaukee and land in Chicago each week. The most common flight departure day for this route is Mon, with 21% 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

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

United Airlines Flights From Milwaukee to Chicago

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