Eric if you decide on Southwest Wisconsin and want to avoid the Chicago mess.
Take IL 17 west to IL 18 West to I 39 North, which will connect you to I90/94. That's the quick way.
My way would be to take Il 17 west to Dwight, at the 4-way stop coming into Dwight take IL 47 North to Dupont road( This is where curves start ), ride along the Illinois river bluff to IL 23 in Ottawa, take 23 North a few blocks to IL 71 west, that will get you a nice set of twisties to Starved Rock State Park. Watch for the North entrance to the park once you get on top of the hill,you do want to ride the park, come out the east side of the park and go north on IL 178 through Utica to I 80 west to IL 40 north.
IL 40 will end at IL 78, IL 78 north will continue all the way to Wisconsin turning into WI 78. It's a good ride just staying on 78 all the way to WI 33 that will take you west into La Crosse if that's where you want to go.