And from both southern US coasts.

Since you want the kilt to essentially be treated like a pair of jeans, I guess I'd consider how much I'd be willing to pay for jeans and use that as a guideline when looking at kilts.

I have 2 SWK standards and like the feel of the weight. I'm not around the kind of wind you might have whipping around the buildings in Chicago, so I'm not sure how they'd do. When I have been in a breeze I've usually found the wind might lift one side, keep the other side down, and expose nothing more than thigh.