I'm in the Chicago area and "Windy City" is, unfortunately, a reference to politics, not wind. We don't get many days of really strong wind, but I have vented kites that are made for that purpose. I find it uncomfortable to fly in wind that is pushing me around, so I avoid anything over 16 mph, or thereabouts. I have kites that can handle wind over 40 mph and have flown in wind over 25 mph three or four times. Over 35 mph, once, for about 5 minutes and then headed for the bar. Don't get me wrong, though. If you enjoy it, go for it. I found it invigorating the first couple of times, but soon realized that my true passion is flying in wind so slow that most kites are grounded. Get the right kite for the wind you'll be flying, as too much pressure in the sail of a kite not designed for it will eventually, if not immediately, destroy the kite or at least cause premature wear.