Hey Roadie.
Traffic around Chicago can be horrendous and dangerous…worse than Toronto.
I did an Iron Butt back in 2013 and found a great way to avoid it
https://goo.gl/maps/TnsHo6BPgJE2
I started Saturday morning around 5:30am and there was none too little traffic all the way to Wisconsin.
Now I’m not suggesting that you do an Iron Butt but leaving that early in the morning on a Saturday or Sunday can be advantages to you.
If you don’t do the expensive ferry route then realistically you’re looking at 2.5 to 3 days to get there.
Then the same to get back.
That’s eating up a lot of time of your holidays to get there and back
(Unless of course you are retired
J)_
Another option is to go across the top (Mackinaw City – Escanaba area)
I did this in 2014 averaging 900km a day.
Less traffic and nice area.
Once you make your way to I94 its smooth sailing.
If I were to do it now….I would truck my bike to Calgary and fly out and meet her.
Do Banff then Glacier NP then Great Falls, Beartooth Pass, Yellowstone then onto Sturgis and then ride back.