Bloomington, Il is at the midpoint.
Davenport, Ia
Brooklyn, Missouri.
Chicago is EAST of Des Moines, Iowa.
Brule, NE
Stockton, IA
Gary, IN
Cincinnati, OH
West Des Moines, Iowa
Hillsdale, IL
Des Moines, IA
Galesburg, IL
It is 333.37 miles accrding to MapQuest.