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 294 miles according to Google Maps.
It is 347 miles according 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 151 miles according to Google Maps.
285 miles. http://maps.google.com/maps?hl=en&q=Chicago+to+Clarkston+Michigan&ie=UTF8&z=7
88 miles between Pontica Illinois and Chicago Illinois.