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Cheap flights from Milwaukee to Chicago from $133

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 9/11. 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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Cheap round-trip flights

Southwest Logo
6:35 pm - 10:50 pmMKE-MDW
4h 15m1 stop
Southwest Logo
3:25 pm - 9:00 pmMDW-MKE
5h 35m1 stop
$237Southwest
Find Deal
Mon, Sep 15 - Mon, Sep 22
Southwest Logo
12:05 pm - 4:10 pmMKE-MDW
4h 05m1 stop
Southwest Logo
5:25 am - 10:00 amMDW-MKE
4h 35m1 stop
$257Southwest
Find Deal
Thu, Sep 11 - Sun, Sep 14
Southwest Logo
6:35 pm - 10:50 pmMKE-MDW
4h 15m1 stop
Southwest Logo
6:05 pm - 9:35 pmMDW-MKE
3h 30m1 stop
$288Southwest
Find Deal
Mon, Sep 15 - Mon, Sep 22
Southwest Logo
6:35 pm - 10:50 pmMKE-MDW
4h 15m1 stop
Southwest Logo
5:10 am - 10:00 amMDW-MKE
4h 50m1 stop
$297Southwest
Find Deal
Fri, Sep 12 - Mon, Sep 15
Southwest Logo
6:35 pm - 10:50 pmMKE-MDW
4h 15m1 stop
Southwest Logo
3:25 pm - 11:00 pmMDW-MKE
7h 35m2 stops
$322Southwest
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Fri, Sep 12 - Mon, Sep 15
Southwest Logo
11:25 am - 3:50 pmMKE-MDW
4h 25m1 stop
Southwest Logo
6:05 pm - 9:35 pmMDW-MKE
3h 30m1 stop
$349Southwest
Find Deal
Fri, Sep 19 - Fri, Sep 19

Southwest flights from Milwaukee to Chicago Midway Airport

Our best Southwest deals on Milwaukee to Chicago Midway Airport flight tickets
Southwest
Sep 15
MKE6:35 pmMilwaukee-Mitchell
4h 15m
1 stop
MDW10:50 pmChicago Midway
Sep 22
MDW3:25 pmChicago Midway
5h 35m
1 stop
MKE9:00 pmMilwaukee-Mitchell
$237
Find similar
Southwest
Sep 11
MKE12:05 pmMilwaukee-Mitchell
4h 05m
1 stop
MDW4:10 pmChicago Midway
Sep 14
MDW5:25 amChicago Midway
4h 35m
1 stop
MKE10:00 amMilwaukee-Mitchell
$257
Find similar
Southwest
Sep 15
MKE6:35 pmMilwaukee-Mitchell
4h 15m
1 stop
MDW10:50 pmChicago Midway
Sep 22
MDW6:05 pmChicago Midway
3h 30m
1 stop
MKE9:35 pmMilwaukee-Mitchell
$288
Find similar

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 August 20, 2025.
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

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Mon 9/15

6:35 pm-10:50 pm

1 stop4h 15m

Chicago Midway

Mon 9/22

3:25 pm-9:00 pm

1 stop5h 35m

$237

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Thu 9/11

12:05 pm-4:10 pm

1 stop4h 05m

Chicago Midway

Sun 9/14

5:25 am-10:00 am

1 stop4h 35m

$257

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Mon 9/15

6:35 pm-10:50 pm

1 stop4h 15m

Chicago Midway

Mon 9/22

6:05 pm-9:35 pm

1 stop3h 30m

$288

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Fri 9/12

6:35 pm-10:50 pm

1 stop4h 15m

Chicago Midway

Mon 9/15

5:10 am-10:00 am

1 stop4h 50m

$297

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Fri 9/12

6:35 pm-10:50 pm

1 stop4h 15m

Chicago Midway

Mon 9/15

3:25 pm-11:00 pm

2 stops7h 35m

$322

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Fri 9/19

11:25 am-3:50 pm

1 stop4h 25m

Chicago Midway

Fri 9/19

6:05 pm-9:35 pm

1 stop3h 30m

$349

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Thu 9/11

12:53 pm-8:53 am

1 stop20h 00m

$133

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Thu 9/25

12:05 pm-4:10 pm

1 stop4h 05m

$139

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Thu 9/11

12:53 pm-4:43 pm

2 stops27h 50m

$178

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Sun 11/30

8:40 pm-11:55 pm

1 stop3h 15m

$189

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 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 airline that flies from Milwaukee-Mitchell to Chicago Midway?

Southwest is the most popular carrier operating from Milwaukee-Mitchell to Chicago Midway

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

Direct flights

None
There are no direct flights from Milwaukee to Chicago Midway Airport. There are no popular flight routes from Milwaukee to Chicago Midway Airport.
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  • 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 4h 05m.

  • 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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
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?

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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