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davidcyclebackThe best antique stores may be along the drive between Chicago and Milwaukee. When I lived in the Upper Midwest, many of the quality antique stores were in the small towns.
If you're looking for side trip, Madison WI is a fine city, home of one of the more beautiful college campuses and state capital buildings, nice downtown, lots of Frank Lloyd Wright architecture (he was from Southern WI) and I'm sure an antique store or two. The downtown is geographically unusual in that it is built on a thin isthmus between two scenic lakes. One lake has the university campus, the other lake the Frank Lloyd Wright civic center and inbetween are the capital and downtown. At the center of the isthmus it's about a fifteen minute walk across.