Live in Chicago and am seeking some good backroad driving routes in Southern Wisconsin. All ideas welcome

Holy hill area if I remember correctly. I grew up in milwaukee, but wasn't really into the "fun drives" at age 16...lol

Try some of the roads up to and around Galena, Illinois. If you go on a Sunday you'll find them pretty deserted. Lots of hills and twisties on glass smooth roads. Fun enough that when you get done with one section you'll want to turn around and do it again!

Try the Sunday brunch at Eagle Ridge Resort. Eleven dollars will get you all the GREAT food you can eat. Premium gas is also about 40 cents cheaper than the Chicago area.

Just take I-88 west and then go north on Route 78 to Elizabeth Route. Follow that north and west. Take any of the highways around there for some roller coaster like driving.

Take Rte 67N thru Elkhorn and into the Kettle all the way to Oconomowoc
Great open road, no stops some good twists / turns

I don't know when you're looking to go, but the Milwaukee region is having their Spring Tour this Saturday (June 9th) through SE Wisconsin.

http://www.porschepark.org

I don't know if you are still looking but go up Int. 90-94 to the hwy 78 exit toward Merrimac. Lot's of twisties and good runs to get up the speed. Take hwy 78 on to Prairie du sac and it's even more fun but the road does deteriate some though. LOTS of smiles per mile.

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Similar response, but about a year later... Milwaukee PCA is going to have their Spring Tour on 7 June. Here's a link if you're interested:

Porsche Club of America - Milwaukee Region: Journal - The Tour Tradition Continues...