I grew up in Chicago and fished a lot in Wisconsin. Your post has reminded me of a favorite trout stream from long ago, the Namekagon River. I remember a stretch near Hayward that use to produce some very large browns (5-6 lbs.) That was many years ago so I can't help with current recommendations. I remember casting buggers to undercut banks on small islands and, besides getting snaged on roots a lot and loosing a lot of flies, I managed to hook some big browns when stripping back accross the stream.

While I love fishing for all fish, there is something about trout.