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Cheap flights from Milwaukee to Chicago from $72

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 5/19. 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
1 adult, Economy, 0 bags

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Find the cheapest flights from Milwaukee to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
4:05 pm - 4:55 pm
MKE
-
MDW
0h 50mnonstop
Southwest Logo
10:10 am - 10:55 am
MDW
-
MKE
0h 45mnonstop
$143Southwest
Tue, Apr 21 - Tue, Apr 28
Southwest Logo
10:15 am - 4:55 pm
MKE
-
MDW
6h 40m
1 stop
Southwest Logo
9:00 pm - 9:45 pm
MDW
-
MKE
0h 45mnonstop
$153Southwest
Tue, Apr 21 - Tue, Apr 28
Southwest Logo
4:30 pm - 10:15 pm
MKE
-
MDW
5h 45m
1 stop
Southwest Logo
4:40 pm - 10:15 pm
MDW
-
MKE
5h 35m
1 stop
$163Southwest
Tue, Apr 21 - Tue, Apr 28
Southwest Logo
4:50 pm - 5:40 pm
MKE
-
MDW
0h 50mnonstop
Southwest Logo
10:00 am - 10:45 am
MDW
-
MKE
0h 45mnonstop
$196Southwest
Thu, Apr 16 - Sun, Apr 19
Southwest Logo
5:40 am - 6:35 am
MKE
-
MDW
0h 55mnonstop
Southwest Logo
9:30 pm - 10:15 pm
MDW
-
MKE
0h 45mnonstop
$201Southwest
Sat, Apr 18 - Mon, Apr 20
Southwest Logo
5:50 am - 6:45 am
MKE
-
MDW
0h 55mnonstop
Southwest Logo
7:50 am - 3:15 pm
MDW
-
MKE
7h 25m
1 stop
$202Southwest
Thu, Apr 23 - Thu, Apr 30
Southwest Logo
4:50 pm - 5:40 pm
MKE
-
MDW
0h 50mnonstop
Southwest Logo
10:00 am - 10:45 am
MDW
-
MKE
0h 45mnonstop
$205Southwest
Thu, Apr 16 - Sun, Apr 19
Southwest Logo
8:00 am - 12:00 pm
MKE
-
MDW
4h 00m
1 stop
Southwest Logo
10:00 am - 10:45 am
MDW
-
MKE
0h 45mnonstop
$206Southwest
Thu, Apr 16 - Sun, Apr 19
Southwest Logo
2:00 pm - 2:45 pm
MKE
-
MDW
0h 45mnonstop
Southwest Logo
5:40 pm - 11:00 pm
MDW
-
MKE
5h 20m
1 stop
$211Southwest
Sat, Apr 18 - Mon, Apr 20
Southwest Logo
8:00 am - 12:00 pm
MKE
-
MDW
4h 00m
1 stop
Southwest Logo
10:00 am - 10:45 am
MDW
-
MKE
0h 45mnonstop
$215Southwest
Thu, Apr 16 - Sun, Apr 19

Southwest flights from Milwaukee to Chicago Midway Airport

Our best Southwest deals on Milwaukee to Chicago Midway Airport flight tickets
Southwest
Apr 21
MKE4:05 pmMilwaukee-Mitchell
0h 50m
MDW4:55 pmChicago Midway
Apr 28
MDW10:10 amChicago Midway
0h 45m
MKE10:55 amMilwaukee-Mitchell
$143
Southwest
Apr 21
MKE10:15 amMilwaukee-Mitchell
6h 40m
1 stop
MDW4:55 pmChicago Midway
Apr 28
MDW9:00 pmChicago Midway
0h 45m
MKE9:45 pmMilwaukee-Mitchell
$153
Southwest
Apr 21
MKE4:30 pmMilwaukee-Mitchell
5h 45m
1 stop
MDW10:15 pmChicago Midway
Apr 28
MDW4:40 pmChicago Midway
5h 35m
1 stop
MKE10:15 pmMilwaukee-Mitchell
$163

Frontier flights from Milwaukee to Chicago Midway Airport

Our best Frontier deals on Milwaukee to Chicago Midway Airport flight tickets
Frontier
Apr 16
MKE12:21 pmMilwaukee-Mitchell
19h 38m
1 stop
MDW7:59 amChicago Midway
Apr 19
MDW9:04 amChicago Midway
32h 24m
2 stops
MKE5:28 pmMilwaukee-Mitchell
$314
Frontier
Apr 12
MKE7:02 pmMilwaukee-Mitchell
48h 29m
2 stops
MDW7:31 pmChicago Midway
Apr 19
MDW2:15 pmChicago Midway
23h 37m
2 stops
MKE1:52 pmMilwaukee-Mitchell
$349
Frontier
Apr 12
MKE7:02 pmMilwaukee-Mitchell
48h 29m
2 stops
MDW7:31 pmChicago Midway
Apr 19
MDW2:15 pmChicago Midway
27h 13m
1 stop
MKE5:28 pmMilwaukee-Mitchell
$398

momondo Fare Finder

 
Customize your flight search to find flights from Milwaukee to Chicago Midway Airport 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 March 29, 2026.
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 - MDW

MKEMDW

Milwaukee-Mitchell

Tue 4/21

4:05 pm-4:55 pm

Nonstop0h 50m

Chicago Midway

Tue 4/28

10:10 am-10:55 am

Nonstop0h 45m

$143

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Tue 4/21

10:15 am-4:55 pm

1 stop6h 40m

Chicago Midway

Tue 4/28

9:00 pm-9:45 pm

Nonstop0h 45m

$153

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Tue 4/21

4:30 pm-10:15 pm

1 stop5h 45m

Chicago Midway

Tue 4/28

4:40 pm-10:15 pm

1 stop5h 35m

$163

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Thu 4/16

4:50 pm-5:40 pm

Nonstop0h 50m

Chicago Midway

Sun 4/19

10:00 am-10:45 am

Nonstop0h 45m

$196

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Sat 4/18

5:40 am-6:35 am

Nonstop0h 55m

Chicago Midway

Mon 4/20

9:30 pm-10:15 pm

Nonstop0h 45m

$201

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Thu 4/23

5:50 am-6:45 am

Nonstop0h 55m

Chicago Midway

Thu 4/30

7:50 am-3:15 pm

1 stop7h 25m

$202

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Thu 4/16

4:50 pm-5:40 pm

Nonstop0h 50m

Chicago Midway

Sun 4/19

10:00 am-10:45 am

Nonstop0h 45m

$205

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Thu 4/16

8:00 am-12:00 pm

1 stop4h 00m

Chicago Midway

Sun 4/19

10:00 am-10:45 am

Nonstop0h 45m

$206

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Sat 4/18

2:00 pm-2:45 pm

Nonstop0h 45m

Chicago Midway

Mon 4/20

5:40 pm-11:00 pm

1 stop5h 20m

$211

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Thu 4/16

8:00 am-12:00 pm

1 stop4h 00m

Chicago Midway

Sun 4/19

10:00 am-10:45 am

Nonstop0h 45m

$215

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 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

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

According to our data, Monday is the cheapest day to fly to Chicago Midway Airport from Milwaukee. The lowest ticket price found for a Monday departure recently was $389. 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, Thursday 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 $448.

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 $386 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $431. 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-Mitchell to Chicago Midway flights?

There is only 1 cabin class available to choose from on Milwaukee-Mitchell to Chicago Midway 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

$211

Fastest flight time

0h 50m

Direct flights

Mon, Tue, Wed, Fri, Sat and Sun
The best one-way flight to Chicago Midway Airport from Milwaukee in the past 72 hours is $211. The best round-trip flight deal from Milwaukee to Chicago Midway Airport found on momondo in the last 72 hours is $378.
The fastest flight from Milwaukee to Chicago Midway Airport takes 0h 50m
Direct flights go from Milwaukee to Chicago Midway Airport on Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
Search flight deals

  • 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?

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
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?

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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