Chicago to Milwaukee (and back?)
 

I rode this last year, got kind of lost in Racine but found a knowledgeable guy who escorted me to the outskirts of Milwaukee. I want to do it again. I can't find detailed instructions on the internet. Three questions:

1. Anyone got a decent route they can share?

2. If you were gonna ride with a friend (90 miles) would you do a 2 person pace line or just relax?

3. Have been riding 30-40 mles 4-5 days a week. (2 centuries last year, none yet this year) Would you attempt a next day return? (Alternative is to arrange a ride)