Nonstop flights from Milwaukee to Chicago

Southwest Airlines flies this route 12 times a week.

MKEMilwaukee Mitchell International

81 mi · 12 flights a week

MDWChicago Midway International

MKEMDW

When they leave

Milwaukee time

5:45a4:00pFirst departure 5:45 AM, last 4:00 PM

Two in the morning, 5:45 AM to 6:40 AM, then four in the afternoon, 1:30 PM to 4:00 PM.

Every flight

Earliest first

5:45 AM→6:30 AMSouthwest AirlinesBoeing 737 MAX 8Thu, Fri, Sat
5:45 AM→6:30 AMSouthwest AirlinesBoeing 737 MAX 8Sun
6:40 AM→7:30 AMSouthwest AirlinesBoeing 737Tue, Wed, Thu, Fri
1:30 PM→2:20 PMSouthwest AirlinesBoeing 737 MAX 8Sat
3:10 PM→4:00 PMSouthwest AirlinesBoeing 737Tue
3:40 PM→4:30 PMSouthwest AirlinesBoeing 737Wed
4:00 PM→4:50 PMSouthwest AirlinesBoeing 737-700Sun

Schedules last checked Sep 19, 2026. Times are local.

Flying from Milwaukee to Chicago

Southwest Airlines is the only airline flying nonstop from Milwaukee to Chicago, 12 times a week on the Boeing 737, Boeing 737 MAX 8 and Boeing 737-700.

Flights run every day except Mondays, up to 2 a day. The first arrival in Chicago is at 6:30 AM and the last at 4:50 PM. The flight covers 81 miles.

Flying back, Chicago to Milwaukee has 14 nonstop flights a week. From Milwaukee, O'Hare (ORD) is the other Chicago area airport with nonstop flights, 108 a week.