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Sheridan road is fun for the 90 sec between Tower rd and Scott ave in Winnetka - I've been driving that little spot since I was in high school.
LSD is horrible, too many potholes, bumps, assholes. Not many cops though if you go at the right time. I used to hit a solid 100mph on my commute into work at 9:30am after traffic cleared out.
Kettle Moraine is about the best you'll find within a 2 hr drive. Stay up in Lake Geneva for a weekend and cruise around, it's worth it.
There are also some rally companies out there who do that stuff regularly with some amenities - all over the country actually.
Chicago Rally
Black List Rally
Corsa America
The Fast Lane Rally
North Face Rally
Gold Rush Rally
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