We recently ran the Bus through (around, actually) Chicago on the way to the Elkhart area. I-294, the Tri State Tollway, is the only way to attempt it. There's always construction in and around Chicago but going through it on I-94 is not something I would care to do. We take the I-294 bypass to I-80.
The biggest trick to handling Chicago is to be there when nobody else is. If we leave so that we run around Chicago after 8 PM on a weeknight, or mid afternoon on a Sunday, it's not so bad. There is generally heavy traffic but at those times it moves along so it's not going to cost you time. Get there during rush hour though and you'll be in bumper to bumper stuff.
Mark & Leann Quasius
2016 Cornerstone 45A
2007 Allegro Bus 42QRP (Sold)
2012 Jeep Wrangler Unlimited - Rubicon