We go to Chicago for a trade show in January of odd numbered years. I can't comment about whether Chicago is kilt friendly or not, but the weather this past year certainly wasn't encouraging for kilt wearing.

Living in the San Diego area as I have for most of the last 20 years the blood has really thinned. I'm not very interested in wearing the kilt in single digit temperatures. (Of course, I'm not really interested in BEING ANYWHERE in single digit temperatures).