GRIMJIM.......sorry man, we do everything in our power to avoid riding thru Chicago. 
You and me both brother.
I did this once...My ride took me from out here in the sticks to Decatur, Bloomington, Rockford, Janesville, then I veered to the east of Madison on my way to Osh Kosh and the greatest airshow on earth.
My return took this hayseed straight through Milwakee and on down straight to Michigan Ave in Chicago and I let my softail clone cruise right on through. I did circle the block a couple times trying to get into
The Navy pier for lunch but it was not to be as there was no parking, even for a bike.
My 800 Vulcan Classic recieved much more favorable reactions from the go-fast boy's on their track bikes to even some women on the street than I ever thought it would while in the windy city.
That Vulcan develops a bunch of torque even with a passenger at low speed but will also run like the fastest land animal known to man (the stripped ass ape) if you crack the throttle so it was easy to leave myself an out and stay out of the way as I ran it hard on I-55 south just long enough to get to the Kankakee exit and those blessed two lanes that I like to ride.
I saw the most custom bikes in the Rockford, Janesville area and I think that they have a Support Your Locals or a Flying Skull chapter up there. Well, that Kawasaki didn't need any fuel so I just let it run on through.
I had also taken those back roads or two lanes on up to Wheaton to the S/A gunleather shop. I had planned another trip up to the libertyville harley dealership using those same roads but didn't make it this summer. I will usually ride around 5,500 miles a year not counting trips but rode just 300miles last summer as I was a Cancer patient and very Ill for the most part.
If you guys come through this area in 09' I might just join up as I am close to I-55 & within 1-1/2hr of St Louis & 3-1/2hr of Chicago.
