From someone who knows that neck of the woods.....
UA has UA Express (Great Lakes Aviation) with some commuter flights from MSP to different places in WI, IA, Upper Michigan, and MN.... the fare allows you to fly a commuter and transfer in one of these cities in route to Chicago: MSP--Ironwood--Chicago--Kalamazoo, MSP--Iron Mountain--Chicago--Kalamazoo, and like that. They used to fly more routes out of MSP (like nonstop to Sioux City, Des Moines, Rhinelander), but their map at the website, effective 2 weeks ago, really only shows Ironwood and Iron Mountain.
Check out their website at
http://www.greatlakesav.com/routes.htm
EPS is right: you will somehow end up in Chicago, then Chicago nonstop to Kalamazoo, but the options are between MSP and ORD if you don't want to fly nonstop.
Keep in mind that in order to get an extra segment in Mileage Plus, you MUST change flight numbers... so UA 6631 MSP-Ironwood connecting to UA 6631 Ironwood--Iron Mountain counts as the same flight (=500 min. MSP--Ironwood--Iron Mountain), but connecting onto UA 6664 Iron Mountain--ORD does count as a separate segment.
Good luck! I hope you don't mind flying for hours in a 19 passenger Beechcraft. ;P
[This message has been edited by Viajero Joven (edited 06-28-2001).]