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Cheap flights from Milwaukee to Chicago from $99

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 6/9. 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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Find the cheapest flights from Milwaukee to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
4:10 pm - 5:00 pm
MKE
-
MDW
0h 50mnonstop
Southwest Logo
9:10 pm - 10:00 pm
MDW
-
MKE
0h 50mnonstop
$197Southwest
Tue, Jun 9 - Tue, Jun 16
Southwest Logo
12:25 pm - 3:55 pm
MKE
-
MDW
3h 30m
1 stop
Southwest Logo
9:10 pm - 10:00 pm
MDW
-
MKE
0h 50mnonstop
$207Southwest
Tue, Jun 9 - Tue, Jun 16
Southwest Logo
6:00 am - 6:50 am
MKE
-
MDW
0h 50mnonstop
Southwest Logo
10:20 am - 11:05 am
MDW
-
MKE
0h 45mnonstop
$208Southwest
Tue, Jun 9 - Thu, Jun 11
Southwest Logo
6:00 am - 6:50 am
MKE
-
MDW
0h 50mnonstop
Southwest Logo
2:35 pm - 10:25 pm
MDW
-
MKE
7h 50m
1 stop
$213Southwest
Wed, Jun 17 - Wed, Jun 24
Southwest Logo
8:05 am - 12:25 pm
MKE
-
MDW
4h 20m
1 stop
Southwest Logo
9:10 pm - 10:00 pm
MDW
-
MKE
0h 50mnonstop
$217Southwest
Tue, Jun 9 - Tue, Jun 16
Southwest Logo
4:00 pm - 4:50 pm
MKE
-
MDW
0h 50mnonstop
Southwest Logo
8:55 pm - 9:45 pm
MDW
-
MKE
0h 50mnonstop
$218Southwest
Sat, Jun 6 - Sat, Jun 13
Southwest Logo
5:05 pm - 6:00 pm
MKE
-
MDW
0h 55mnonstop
Southwest Logo
10:20 am - 11:05 am
MDW
-
MKE
0h 45mnonstop
$219Southwest
Sun, Jun 7 - Fri, Jun 12
Southwest Logo
4:40 pm - 9:55 pm
MKE
-
MDW
5h 15m
1 stop
Southwest Logo
9:10 pm - 10:00 pm
MDW
-
MKE
0h 50mnonstop
$227Southwest
Sat, Jul 18 - Wed, Jul 22
Southwest Logo
12:25 pm - 5:10 pm
MKE
-
MDW
4h 45m
1 stop
Southwest Logo
5:10 pm - 10:25 pm
MDW
-
MKE
5h 15m
1 stop
$228Southwest
Tue, Jun 9 - Tue, Jun 16
Southwest Logo
5:50 pm - 11:00 pm
MKE
-
MDW
5h 10m
1 stop
Southwest Logo
9:55 pm - 10:45 pm
MDW
-
MKE
0h 50mnonstop
$229Southwest
Thu, Jun 11 - Thu, Jun 18

Southwest flights from Milwaukee to Chicago Midway Airport

Our best Southwest deals on Milwaukee to Chicago Midway Airport flight tickets
Southwest
Jun 9
MKE4:10 pmMilwaukee-Mitchell
0h 50m
MDW5:00 pmChicago Midway
Jun 16
MDW9:10 pmChicago Midway
0h 50m
MKE10:00 pmMilwaukee-Mitchell
$197
Southwest
Jun 9
MKE12:25 pmMilwaukee-Mitchell
3h 30m
1 stop
MDW3:55 pmChicago Midway
Jun 16
MDW9:10 pmChicago Midway
0h 50m
MKE10:00 pmMilwaukee-Mitchell
$207
Southwest
Jun 9
MKE6:00 amMilwaukee-Mitchell
0h 50m
MDW6:50 amChicago Midway
Jun 11
MDW10:20 amChicago Midway
0h 45m
MKE11:05 amMilwaukee-Mitchell
$208

Delta flights from Milwaukee to Chicago Midway Airport

Our best Delta deals on Milwaukee to Chicago Midway Airport flight tickets
Delta
Aug 12
MKE9:22 amMilwaukee-Mitchell
8h 39m
1 stop
MDW6:01 pmChicago Midway
Aug 18
MDW9:59 amChicago Midway
9h 38m
1 stop
MKE7:37 pmMilwaukee-Mitchell
$365
Delta
Aug 12
MKE7:52 amMilwaukee-Mitchell
10h 09m
1 stop
MDW6:01 pmChicago Midway
Aug 20
MDW9:59 amChicago Midway
9h 38m
1 stop
MKE7:37 pmMilwaukee-Mitchell
$395
Delta
Aug 13
MKE9:22 amMilwaukee-Mitchell
8h 39m
1 stop
MDW6:01 pmChicago Midway
Aug 15
MDW1:52 pmChicago Midway
7h 50m
1 stop
MKE9:42 pmMilwaukee-Mitchell
$425

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 May 15, 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

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Tue 6/9

4:10 pm-5:00 pm

Nonstop0h 50m

Chicago Midway

Tue 6/16

9:10 pm-10:00 pm

Nonstop0h 50m

$197

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Tue 6/9

12:25 pm-3:55 pm

1 stop3h 30m

Chicago Midway

Tue 6/16

9:10 pm-10:00 pm

Nonstop0h 50m

$207
Quickest round-trip

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Tue 6/9

6:00 am-6:50 am

Nonstop0h 50m

Chicago Midway

Thu 6/11

10:20 am-11:05 am

Nonstop0h 45m

$208

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Wed 6/17

6:00 am-6:50 am

Nonstop0h 50m

Chicago Midway

Wed 6/24

2:35 pm-10:25 pm

1 stop7h 50m

$213

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Tue 6/9

8:05 am-12:25 pm

1 stop4h 20m

Chicago Midway

Tue 6/16

9:10 pm-10:00 pm

Nonstop0h 50m

$217

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Sat 6/6

4:00 pm-4:50 pm

Nonstop0h 50m

Chicago Midway

Sat 6/13

8:55 pm-9:45 pm

Nonstop0h 50m

$218

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Sun 6/7

5:05 pm-6:00 pm

Nonstop0h 55m

Chicago Midway

Fri 6/12

10:20 am-11:05 am

Nonstop0h 45m

$219

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Sat 7/18

4:40 pm-9:55 pm

1 stop5h 15m

Chicago Midway

Wed 7/22

9:10 pm-10:00 pm

Nonstop0h 50m

$227

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Tue 6/9

12:25 pm-5:10 pm

1 stop4h 45m

Chicago Midway

Tue 6/16

5:10 pm-10:25 pm

1 stop5h 15m

$228

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Thu 6/11

5:50 pm-11:00 pm

1 stop5h 10m

Chicago Midway

Thu 6/18

9:55 pm-10:45 pm

Nonstop0h 50m

$229

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, Wednesday is the cheapest day to fly to Chicago Midway Airport from Milwaukee. The lowest ticket price found for a Wednesday departure recently was $391. 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, Sunday 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 $446.

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 $424. 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

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

Every day
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 $344.
The fastest flight from Milwaukee to Chicago Midway Airport takes 0h 50m
Direct flights go from Milwaukee to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Milwaukee to Chicago Midway Airport

  • 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
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?

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.

An easier way to manage your Chicago Midway Airport trip

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