There is no city on the border of the City of Chicago and the State of Michigan, as the two never touch.
The flight distance from Chicago, Illinois to Kalamazoo, Michigan is: 110 miles / 178 km
Thank you for allowing me to type Kalamazoo, MI.
It is 140 miiles accrding to Google Maps.
It is 181 miles according to Google Maps.
It is 147 miles according to Google Maps.
It is 407 miles according to Google Maps.
It is 284 miles according to Google Maps.
It is 347 miles according to Google Maps.
It is 151 miles according to Google Maps.
285 miles. http://maps.google.com/maps?hl=en&q=Chicago+to+Clarkston+Michigan&ie=UTF8&z=7
The driving distance from Detroit, Michigan to Chicago, Illinois is 283 miles.