Never been to Chicago but I lived in Philly for 13 years so I'm well versed in riding in all conditions. Hail, rain, sleet, snow.... I've ridden it all. Rode back from Cape Cod in 110 degrees, and once I rode from NJ back to Philly in a proper ice storm. The Betsy Ross Bridge was coated in a good 3"- 4" of ice and I skied my '97 Harley Road King across in second gear at about 12mph while chanting "please don't fall, please don't fall, please don't fall" for the (approx) 5-10 minutes it took me to cross. A man will do strange things for a piece of ass 🤣