Gets a bit chilly in Scotland in the winter but I visited Chicago in April a few years ago. First day went on a fantastic walking tour of the architectural history of the city. I was dressed in tee shirt and a light jacket and mid way through the walk it started blowing a gale and snowing up a blizzard.

My friend and I could only collapse in helpless laughter (the alternative was to die from hypothermia). Our fellow culture seekers looked at us as if we were mad (but we fooled them- we looked back as if we weren't )

Coldest April they'd had in years apparently...and whatdy'a know - no gloves or scarves available in the shops which were full of little summer tops and dresses! First time I've been glad to get back to Scotland for the heat!

Chicago's a great city tho' - full of brilliant buildings (big Frank Lloyd Wright fan here)

But CWR probably wins on the chill factor.