Nonstop flights from Chicago to Milwaukee
Southwest Airlines flies this route twice a day.
MDWChicago Midway International
81 mi · 14 flights a week
MKEMilwaukee Mitchell International
When they leave
Chicago time10:10a8:40pFirst departure 10:10 AM, last 8:40 PM
Three in the morning, 10:10 AM to 10:25 AM, then two in the evening, 6:15 PM to 8:40 PM.
Every flight
Earliest first
Schedules last checked Sep 19, 2026. Times are local.
Flying from Chicago to Milwaukee
Southwest Airlines is the only airline flying nonstop from Chicago to Milwaukee, twice a day on the Boeing 737-700, Boeing 737 and Boeing 737 MAX 8.
The first arrival in Milwaukee is at 11:00 AM and the last at 9:25 PM. The flight covers 81 miles.
Flying back, Milwaukee to Chicago has 12 nonstop flights a week. O'Hare (ORD) also has nonstop flights to Milwaukee, 104 a week.
Return flights
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Schedules as of Oct 9, 2026.