FFL Helper
Chicago CHI
$147
MKE → MDW · Southwest Airlines
FFL Helper / Milwaukee / Chicago / September 2026
MKE → CHI · 2026-09
Milwaukee to Chicago in September 2026
Dated one-way fares from Milwaukee to Chicago in September 2026. Use the calendar to see which days are cheaper.
Lowest this month
$147
Highest this month
$147
Sample fare
$147
Airports
MKE–MDW
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Other months: September 2026 · Full route
September 2026 price calendar
September 2026
From $147
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$147
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Dated fares
Booking MKE to CHI in September 2026
This page is only September 2026 on the Milwaukee to Chicago route. Open the full route if you want the next months side by side.
Prices move as seats sell. Confirm the live itinerary before you book Milwaukee to Chicago in September 2026.