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

Frontier, Southwest, and Delta are the most popular carriers operating from Milwaukee-Mitchell to Chicago Midway

What day of the week experiences the fewest flight delays on this route?

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Friday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Milwaukee to Chicago flights?

According to our data, Frontier have had the least number of delays on this route over the last 12 months; with no flights being classified as delayed.

How often are flights from Milwaukee to Chicago delayed?

Historically, on average around 22% of flights between Milwaukee and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 83 minutes.

What is the most punctual flight time for Milwaukee to Chicago flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the early afternoon have, in the past, seen delays more frequently in comparison.

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.

$73 Cheap Flights from Milwaukee to Chicago Midway Airport in 2025/26

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4:05 pm - 8:45 pmMKE-MDW

4h 40m1 stop

6:45 am - 11:05 amMDW-MKE

4h 20m1 stop

$254Southwest

Find Deal

Thu, Dec 4 - Sun, Dec 7

6:09 pm - 9:52 amMKE-MDW

15h 43m2 stops

6:37 pm - 9:39 amMDW-MKE

15h 02m1 stop

$258Multiple Airlines

Find Deal

Sun, Dec 7 - Sun, Dec 14

6:09 pm - 9:52 amMKE-MDW

15h 43m2 stops

6:37 pm - 9:39 amMDW-MKE

15h 02m1 stop

$259Multiple Airlines

Find Deal

Sun, Dec 7 - Sun, Dec 14

5:50 am - 9:55 amMKE-MDW

4h 05m1 stop

6:45 am - 11:05 amMDW-MKE

4h 20m1 stop

$278Southwest

Find Deal

Sun, Dec 7 - Sun, Dec 14

6:09 pm - 9:52 amMKE-MDW

15h 43m2 stops

6:37 pm - 9:39 amMDW-MKE

15h 02m1 stop

$293Multiple Airlines

Find Deal

Sun, Dec 7 - Sun, Dec 14

5:50 am - 6:45 amMKE-MDW

0h 55mnonstop

8:30 pm - 9:15 pmMDW-MKE

0h 45mnonstop

$297Southwest

Find Deal

Sun, May 3 - Sun, May 24

5:00 am - 10:10 amMKE-MDW

5h 10m1 stop

5:25 am - 11:25 amMDW-MKE

6h 00m1 stop

$309Southwest

Find Deal

Fri, Dec 19 - Sun, Dec 21

12:10 pm - 5:50 pmMKE-MDW

5h 40m2 stops

4:15 pm - 9:45 pmMDW-MKE

5h 30m1 stop

$323Southwest

Find Deal

Sun, May 3 - Sun, May 24

11:25 am - 3:20 pmMKE-MDW

3h 55m1 stop

5:25 pm - 11:45 pmMDW-MKE

6h 20m2 stops

$364Southwest

Find Deal

Fri, Dec 19 - Sun, Dec 21

4:52 pm - 8:54 amMKE-MDW

16h 02m1 stop

9:34 am - 4:07 pmMDW-MKE

6h 33m1 stop

$541Delta

Find Deal

Sun, Dec 7 - Sun, Dec 14

Southwest flights from Milwaukee to Chicago Midway Airport

Our best Southwest deals on Milwaukee to Chicago Midway Airport flight tickets

Southwest

Dec 4

MKE4:05 pmMilwaukee-Mitchell

4h 40m

1 stop

MDW8:45 pmChicago Midway

Dec 7

MDW6:45 amChicago Midway

4h 20m

1 stop

MKE11:05 amMilwaukee-Mitchell

$254

Find similar

Southwest

Dec 7

MKE5:50 amMilwaukee-Mitchell

4h 05m

1 stop

MDW9:55 amChicago Midway

Dec 14

MDW6:45 amChicago Midway

4h 20m

1 stop

MKE11:05 amMilwaukee-Mitchell

$278

Find similar

Southwest

Nov 15

MKE5:45 amMilwaukee-Mitchell

6h 00m

1 stop

MDW11:45 amChicago Midway

Nov 18

MDW5:15 pmChicago Midway

4h 15m

1 stop

MKE9:30 pmMilwaukee-Mitchell

$284

Find similar

momondo Fare Finder

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

Thu 12/4

4:05 pm-8:45 pm

1 stop4h 40m

Chicago Midway

Sun 12/7

6:45 am-11:05 am

1 stop4h 20m

$254

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Sun 12/7

6:09 pm-9:52 am

2 stops15h 43m

Chicago Midway

Sun 12/14

6:37 pm-9:39 am

1 stop15h 02m

$258

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Sun 12/7

6:09 pm-9:52 am

2 stops15h 43m

Chicago Midway

Sun 12/14

6:37 pm-9:39 am

1 stop15h 02m

$259

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Sun 12/7

5:50 am-9:55 am

1 stop4h 05m

Chicago Midway

Sun 12/14

6:45 am-11:05 am

1 stop4h 20m

$278

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Sun 12/7

6:09 pm-9:52 am

2 stops15h 43m

Chicago Midway

Sun 12/14

6:37 pm-9:39 am

1 stop15h 02m

$293

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Sun 5/3

5:50 am-6:45 am

Nonstop0h 55m

Chicago Midway

Sun 5/24

8:30 pm-9:15 pm

Nonstop0h 45m

$297

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Fri 12/19

5:00 am-10:10 am

1 stop5h 10m

Chicago Midway

Sun 12/21

5:25 am-11:25 am

1 stop6h 00m

$309

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Sun 5/3

12:10 pm-5:50 pm

2 stops5h 40m

Chicago Midway

Sun 5/24

4:15 pm-9:45 pm

1 stop5h 30m

$323

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Fri 12/19

11:25 am-3:20 pm

1 stop3h 55m

Chicago Midway

Sun 12/21

5:25 pm-11:45 pm

2 stops6h 20m

$364

MilwaukeeChicago

MKE - MDW

MKEMDW

Milwaukee-Mitchell

Sun 12/7

4:52 pm-8:54 am

1 stop16h 02m

Chicago Midway

Sun 12/14

9:34 am-4:07 pm

1 stop6h 33m

$541

Flights are sorted by cheapest round-trip flights first.

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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

Prices

Airlines

Delays

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	$386
Fastest flight time	0h 50m
Direct flights	Fri and Sat

The best flight deal from Milwaukee to Chicago Midway Airport found on momondo in the last 72 hours is $386

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

Direct flights go from Milwaukee to Chicago Midway Airport on Friday and Saturday. 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 55m.
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?
Based on momondo bookings for flights between Milwaukee and Chicago Midway Airport, the leading plane model is Boeing 737 MAX 8, making up 20.00% of the total bookings. Other popular models include Airbus A321-100/200 with 20.00%, Airbus A319 with 20.00%, and Boeing 737-800 Passenger/BBJ2 (winglets) with 20.00%.

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?

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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Cheap flights from Milwaukee to Chicago from $73

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 1/10. 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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Southwest flights from Milwaukee to Chicago Midway Airport

Our best Southwest deals on Milwaukee to Chicago Midway Airport flight tickets

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Use the filters below to find and compare flights from Milwaukee to Chicago Midway Airport that are best for you.

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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 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.

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

Frontier, Southwest, and Delta are the most popular carriers operating from Milwaukee-Mitchell to Chicago Midway

How often are flights from Milwaukee to Chicago delayed?

Historically, on average around 22% of flights between Milwaukee and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 83 minutes.

What is the most punctual flight time for Milwaukee to Chicago flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the early afternoon have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Friday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Milwaukee to Chicago flights?

According to our data, Frontier have had the least number of delays on this route over the last 12 months; with no flights being classified as delayed.

When to book flights from Milwaukee to Chicago Midway Airport

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

Fastest flight time

Direct flights

How far is Milwaukee-Mitchell to Chicago Midway by plane?

When did momondo last update prices for flights from Milwaukee-Mitchell Airport to Chicago Midway Airport?

How old do you have to be to fly from Milwaukee-Mitchell Airport to Chicago Midway Airport?

What documentation or ID do you need to fly to Chicago Midway Airport?

What is the most popular plane model from Milwaukee to Chicago Midway Airport?

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 Midway Airport 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 Chicago

Popular cities in the United States

Popular flights according to clicks in the last 7 days on momondo