Southwest Airlines
Did you mean flights from Chicago to Milwaukee?
United States
General Mitchell International Airport
Switch direction
United States
Midway International Airport
Click to show full flight schedule
Scan through all non-stop flights from Milwaukee to Chicago. The full flight schedule below gives an overview of all non-stop flights from MKE to MDW, which includes the daily timetable of every operating airline for the upcoming 12 months.
Note: for airline-specific flight schedules, please scroll further down.
Known for its continental climate, Chicago features hot, humid summers with temperatures above 30°C (86°F) and cold, snowy winters that often drop below 0°C (32°F). This striking seasonal contrast offers travelers a variety of activities, from summer hiking to winter sports, ensuring year-round appeal.
The best time to visit Chicago is from March to November, covering spring, summer, and fall. While summer can be hot, it also sees slightly more rainfall than other seasons.
Currently, there is only one airline operating non-stop flights from Milwaukee MKE to Chicago MDW, which is Southwest Airlines. This section gives an overview of the flight schedules and timetables of every airline with direct flights for this route.
Click an airline below to view their MKE MDW flight schedule.
Flights from MKE to MDW are operated 14 times a week, with an average of 2 flights per day. Departure times vary between 05:40 - 17:15. The earliest flight departs at 05:40, the last flight departs at 17:15. However, this depends on the date you are flying so please check with the full flight schedule above to see which departure times are available on your preferred date(s) of travel.
On this non-stop route, you can fly in Economy only.
The fastest direct flight from Milwaukee to Chicago takes 55 minutes. The flight distance between Milwaukee and Chicago is 80 miles (or 129 km).
There are 2 airports in Chicago: Midway International Airport (MDW) and O'Hare International Airport (ORD).
There are 14 flights per week flying from Milwaukee to Chicago (as of April 2026).
55 minutes is the average flight time from Milwaukee to Chicago.
The distance from Milwaukee to Chicago is 80 miles (129 kilometers).
Southwest Airlines is the only airline flying nonstop from Milwaukee to Chicago.
There are no alliances flying direct from Milwaukee to Chicago at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from Milwaukee to Chicago:
The earliest flight departs at 05:40 from Milwaukee and arrives at 06:35 at Chicago.
The latest flight departs at 17:15 from Milwaukee and arrives at 18:05 at Chicago.
80 miles (129 km) · 55m
05:40
06:35
Southwest Airlines
WN 353
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
05:45
06:45
Southwest Airlines
WN 1980
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
05:50
06:50
Southwest Airlines
WN 1980
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
05:50
06:45
Southwest Airlines
WN 353
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
05:50
06:45
Southwest Airlines
WN 353
Southwest Airlines
Boeing 757
Y
W
J
F
06:00
07:00
Southwest Airlines
WN 1980
Southwest Airlines
Boeing 757
Y
W
J
F
14:00
14:45
Southwest Airlines
WN 1753
Southwest Airlines
Boeing 757
Y
W
J
F
16:00
16:50
Southwest Airlines
WN 2385
Southwest Airlines
Boeing 757
Y
W
J
F
16:05
16:55
Southwest Airlines
WN 2385
Southwest Airlines
Boeing 757
Y
W
J
F
16:40
17:30
Southwest Airlines
WN 3326
Southwest Airlines
Boeing 757
Y
W
J
F
16:50
17:40
Southwest Airlines
WN 1919
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
16:50
17:40
Southwest Airlines
WN 2385
Southwest Airlines
Boeing 757
Y
W
J
F
16:55
17:45
Southwest Airlines
WN 3572
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
17:10
18:00
Southwest Airlines
WN 2385
Southwest Airlines
Boeing 757
Y
W
J
F
Click to Check Prices
