You could also make your way down to State Line Rd at the SE corner of Rock County, WI, and follow the Grand Illinois Trail cue sheets that are available somewhere on the League of Illinois Bicyclists website at http://www.bikelib.org. Those would take you down the bike trails into Maywood, in the near west suburbs - not too much of a trick to get to the north side from there.
That's where you get the GPS file. Make sure to shut off automatic routing or it's useless. The trails in Kenosha and Racine are worth the entire first leg. There is also fresh pavement going on in the old crushed stone sections.
I doubt you'll have trouble getting a campsite, but check first at Cliffside.
I really don't have much to say because I worked out all the kinks in this route. Just have some nice touring tires, like 28 - 32 if you're riding 700C. I think most 26" tires will do. You will be on a few crushed stone trails. I chose trails because I didn't want to deal with cars - less cars equals fewer close calls, etc.
Don't bother with bringing a stove and food as there are plenty of places to eat on the trails. Do bring a few energy bars, water (water is a big one), and maybe some fruit. There's a great taco place in Waukesha but I don't remember exactly where in town it is.
..and this time of year bring plenty of bug repellant. I like this route in early spring when the 'skeeters haven't quite recovered from winter.
Originally Posted by raoulcousins
I'm trying to plan a tour starting in Chicago. I was thinking of doing Chicago to Madison via the route at: