Quoted:
Also, when traveling through Chicago by car, when is the best time to avoid the traffic?
Having recently moved here, the best advice we were given was to not live in Milwaukee county. We would not have done it anyway, but like minded people we met here ALL said the same thing. Wisconsin has a lot to offer and great people too, missing out on that would be a mistake. They can always drive in to Milwaukee.
I drive through Chicago all the time, an I-Pass is your friend 24/7 but especially when the traffic is heavy. The tolls back up and you drive on by. If you plan to make more than one trip per year, get one. Also, tolls are half price with the pass.
I-Pass
If you come from the Indiana direction, I always go 90 to 90/94 and take the toll roads. You either go in well before rush hour or AFTER 9:30am but you will "fly" through. It is all timing. No reason to be in a rush to sit 2 hours in traffic. Beat it or wait it out. After 1pm on any summer Friday, either direction, it is partly luck. If you can't stomach tolls, test your luck on 94 all the way or 294.
On your return trip, never, never take 80/94 outbound on the South side on any day. It is a crap shoot on traffic. Realize even if you drive 294 on the return trip it will put you on that death trap. Go 94 to 90 and follow 90 out of town.
Last Saturday I went to Indy and back. On my return trip to WI, I saw one of the largest traffic jams I have ever seen on 94 outbound. It was a good reminder why for the last 20 years I never drive that stretch of road. I say this and I have lived in LA and Atlanta. I had detoured from my normal route to see a friend which is the only reason I was even on 94 going in to town on the South side instead of 90.