Does anybody know here I can get (driving) directions from Chicago to San Paulo, Brazil?
Well, you’re going to have to take a boat for part of the journey.
A google search on Darien Gap.
Just get yourself a North American, Central American, and South American road atlas. It can’t be that hard to figure out. But, as Robot Arm points out, you’ll encounter some problems in Panama. Personally, I would start out by going from Chicago to Laredo, Texas (via I-55, I-40, I-440, I-30, I-635, I-20 and I-35), cross the border into Mexico, and go from there.
And don’t forget to make a left at Albuquerque…