best route through Chicago?

I was wondering if someone could give me some guidance on the best
route to take for an upcoming trip? I can run routes based on actual
miles and times in my travel software, but I am looking for more
practical info like "don't go that way, that road will be jammed at
that time of day."

I will be coming into the Chicagoland area from the west on the 88
tollway. My destination is Libertyville, way up north (near Waukegan
or Gurnee). I need to be there by 10am.

If I come clear into the Chicagoland area, I'd be hitting the 88 & the
North/South tollway interchange at about 8:45am.

Microsoft Streets & Trips software says take 88 in, then up the
Tri-state to the Libertyville area. I am doubting that is the "best"
way to go.

Should I go the North/South, to 290? It seems though that once the
290 ends, I've got some "meandering" to do through city roads.

Should I skip Chicago and take I39 up from the 88 to Rockford? Then
take the Northwest tollway back into Chicago area, and at some point
(the Barrington area?) start meandering through city roads to get to
Libertyville.

At that time in the morning, which route would you take?

Thanks!
--multiplaza.nl.nu--