I was hoping you didn't live where i would be afraid to ride (down town). All i know about Chicago is it is in my way when i go to Kentucky, Seems like there is always traffic every time of day. To far away from nice windy scenic roads. I don't know if you ever heard of holy hill up here it is the most incredible riding. It is by the town or Erin where they had a PGA tournament last year. Post some pics of your bike.
2002 V-Star 1100
You don't stop riding when you get old, you get old when you stop riding
2004 BMW K1200GT
1995 BMW 1100 LT
1970 Honda 500/4
1969 Kawasaki 500HD - 3 cylinder rocket
1968 Yamaha 250