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Cheap flights from Milwaukee to Chicago from $91

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 5/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Milwaukee to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
1:46 pm - 2:55 pm
MKE
-
ORD
1h 09mnonstop
United Airlines Logo
8:57 pm - 10:03 pm
ORD
-
MKE
1h 06mnonstop
$181United Airlines
Wed, May 13 - Wed, May 20
Southwest Logo
4:05 pm - 4:55 pm
MKE
-
MDW
0h 50mnonstop
Southwest Logo
9:00 pm - 9:45 pm
MDW
-
MKE
0h 45mnonstop
$181Southwest
Wed, May 13 - Wed, May 20
American Airlines Logo
7:30 am - 8:49 am
MKE
-
ORD
1h 19mnonstop
American Airlines Logo
9:20 pm - 10:23 pm
ORD
-
MKE
1h 03mnonstop
$191American Airlines
Tue, May 26 - Mon, Jun 1
Southwest Logo
5:50 am - 6:45 am
MKE
-
MDW
0h 55mnonstop
Southwest Logo
4:40 pm - 10:15 pm
MDW
-
MKE
5h 35m
1 stop
$191Southwest
Wed, May 13 - Wed, May 20
American Airlines Logo
8:11 am - 9:25 am
MKE
-
ORD
1h 14mnonstop
American Airlines Logo
4:05 pm - 5:07 pm
ORD
-
MKE
1h 02mnonstop
$200American Airlines
Sun, May 10 - Wed, May 13
Southwest Logo
5:50 am - 6:45 am
MKE
-
MDW
0h 55mnonstop
Southwest Logo
9:00 pm - 9:45 pm
MDW
-
MKE
0h 45mnonstop
$200Southwest
Sun, May 10 - Wed, May 13
United Airlines Logo
8:45 pm - 9:54 pm
MKE
-
ORD
1h 09mnonstop
United Airlines Logo
9:33 pm - 10:33 pm
ORD
-
MKE
1h 00mnonstop
$201United Airlines
Thu, May 14 - Mon, May 18
Southwest Logo
4:50 pm - 5:40 pm
MKE
-
MDW
0h 50mnonstop
Southwest Logo
9:30 pm - 10:15 pm
MDW
-
MKE
0h 45mnonstop
$201Southwest
Thu, May 14 - Mon, May 18
Frontier Logo
8:46 am - 11:13 pm
MKE
-
ORD
14h 27m
1 stop
Frontier Logo
5:11 pm - 8:01 am
ORD
-
MKE
14h 50m
1 stop
$206Frontier
Tue, Jun 2 - Wed, Jun 3
Frontier Logo
8:46 am - 7:51 pm
MKE
-
ORD
11h 05m
2 stops
Frontier Logo
5:11 pm - 8:01 am
ORD
-
MKE
14h 50m
1 stop
$224Frontier
Tue, Jun 2 - Wed, Jun 3

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United Airlines flights from Milwaukee to Chicago

Our best United Airlines deals on Milwaukee to Chicago flight tickets
United Airlines
May 13
MKE1:46 pmMilwaukee-Mitchell
1h 09m
ORD2:55 pmChicago O'Hare Intl
May 20
ORD8:57 pmChicago O'Hare Intl
1h 06m
MKE10:03 pmMilwaukee-Mitchell
$181
United Airlines
May 14
MKE8:45 pmMilwaukee-Mitchell
1h 09m
ORD9:54 pmChicago O'Hare Intl
May 18
ORD9:33 pmChicago O'Hare Intl
1h 00m
MKE10:33 pmMilwaukee-Mitchell
$201
United Airlines
May 5
MKE9:37 amMilwaukee-Mitchell
1h 08m
ORD10:45 amChicago O'Hare Intl
May 6
ORD8:57 pmChicago O'Hare Intl
1h 06m
MKE10:03 pmMilwaukee-Mitchell
$251

Frontier flights from Milwaukee to Chicago

Our best Frontier deals on Milwaukee to Chicago flight tickets
Frontier
Jun 2
MKE8:46 amMilwaukee-Mitchell
14h 27m
1 stop
ORD11:13 pmChicago O'Hare Intl
Jun 3
ORD5:11 pmChicago O'Hare Intl
14h 50m
1 stop
MKE8:01 amMilwaukee-Mitchell
$206
Frontier
Jun 2
MKE8:46 amMilwaukee-Mitchell
11h 05m
2 stops
ORD7:51 pmChicago O'Hare Intl
Jun 3
ORD5:11 pmChicago O'Hare Intl
14h 50m
1 stop
MKE8:01 amMilwaukee-Mitchell
$224
Frontier
May 26
MKE8:46 amMilwaukee-Mitchell
14h 27m
1 stop
ORD11:13 pmChicago O'Hare Intl
Jun 1
ORD1:50 pmChicago O'Hare Intl
18h 11m
2 stops
MKE8:01 amMilwaukee-Mitchell
$258

momondo Fare Finder

 
Customize your flight search to find flights from Milwaukee to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated April 18, 2026.
Use the filters below to find and compare flights from Milwaukee to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Wed 5/13

1:46 pm-2:55 pm

Nonstop1h 09m

Chicago O'Hare Intl

Wed 5/20

8:57 pm-10:03 pm

Nonstop1h 06m

$181
Quickest round-trip

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Wed 5/13

4:05 pm-4:55 pm

Nonstop0h 50m

Chicago Midway

Wed 5/20

9:00 pm-9:45 pm

Nonstop0h 45m

$181

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Tue 5/26

7:30 am-8:49 am

Nonstop1h 19m

Chicago O'Hare Intl

Mon 6/1

9:20 pm-10:23 pm

Nonstop1h 03m

$191

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Wed 5/13

5:50 am-6:45 am

Nonstop0h 55m

Chicago Midway

Wed 5/20

4:40 pm-10:15 pm

1 stop5h 35m

$191

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Sun 5/10

8:11 am-9:25 am

Nonstop1h 14m

Chicago O'Hare Intl

Wed 5/13

4:05 pm-5:07 pm

Nonstop1h 02m

$200

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Sun 5/10

5:50 am-6:45 am

Nonstop0h 55m

Chicago Midway

Wed 5/13

9:00 pm-9:45 pm

Nonstop0h 45m

$200

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Thu 5/14

8:45 pm-9:54 pm

Nonstop1h 09m

Chicago O'Hare Intl

Mon 5/18

9:33 pm-10:33 pm

Nonstop1h 00m

$201

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Thu 5/14

4:50 pm-5:40 pm

Nonstop0h 50m

Chicago Midway

Mon 5/18

9:30 pm-10:15 pm

Nonstop0h 45m

$201

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Tue 6/2

8:46 am-11:13 pm

1 stop14h 27m

Chicago O'Hare Intl

Wed 6/3

5:11 pm-8:01 am

1 stop14h 50m

$206

MilwaukeeChicago

MKE - ORD

MKEORD

Milwaukee-Mitchell

Tue 6/2

8:46 am-7:51 pm

2 stops11h 05m

Chicago O'Hare Intl

Wed 6/3

5:11 pm-8:01 am

1 stop14h 50m

$224

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

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 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 $429. 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 $530.

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 $437. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $692.

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

$202

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 $202. The best round-trip flight deal from Milwaukee to Chicago found on momondo in the last 72 hours is $362.
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

Frequently asked questions about flying from Milwaukee to Chicago

  • 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?

  • 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?

  • 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
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $179Free CancellationRating
7.1
11,604 reviews
Search American Airlines flights
United AirlinesPriceFrom $179Free CancellationRating
7.4
9,605 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 55 flights on this route every week with an average price of $224. 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 $199, however, with flight time and availability significantly affecting the price. American Airlines (7.1/10 from 11,604 user reviews) flies into Chicago from Milwaukee 56 times in an average week so prices can vary.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
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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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
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport