If you're two hours north of chicago, you're here in WI. Unhappily, you can be ticketed for having a passenger on a 50cc.
As for the windshield, it's up to you. I have safety glasses from work that hug the face and are great for keeping out wind from my eyes. I'm 6'2", so unless the windshield is really high, it's not going to do much for me, so I don't even think about it. I have a bit of wind resistance, though and, being over 200 pounds, it does have an effect on the speed I can attain.