Hey everyone, sorry for not coming back and chiming in on the thread.
We opted to go the week before - or rather, due to my vacation situation at work, my vacation availability ended up making the decision for us, but it was what we decided we wanted anyways in the end, so it's all good.
As for routing, I'm aware of the Chicago situation. I plan to schedule our transit through Chicago for hopefully a lighter traffic time of day as much as possible, but as someone who lives on the east side of Toronto (so I know traffic) and have been through Chicago many times before (I drive for a living, so been there, done that) it is what it is. I'll be running Waze on my phone for the trips through the major city areas, so if there's anything particularly bad so far as major backups or closures, it'll take us around things as best as possible in the end.
We are also doing a Bun-Burner Iron Butt on the way out (and back as well, but that's another story), so realistically the ferry isn't an option either...although I looked at it since I'm a bit of a ship buff as well, and the SS Badger is a little piece of history that does indeed interest me. But it doesn't fit in with the goals.
I should also mention that myself at least have been in that area before so i know some of the good roads, and have seen the major sights through Yellowstone, etc.
Our actual time in Sturgis, so far as the rally itself, will be basically opening night Friday at this point, probably for the late afternoon and evening...then we call it a night and bail out of town on the first leg of our Iron Butt for the trip home, crossing at Sault Ste Marie on the trip back simply to make the trip home different than the trip out vs a complete backtrack on the roads. I've ridden the stretch between Toronto (home area) and the Soo many times and it's enjoyable as well (certainly way better than the Interstate across IL & MI, then the 401) so it'll be a nice change up as well.
-03 VTX1300S. 3" Hard Krome exhaust, Ultimate Seats, Wide Open Customs batwing.