I've been accused of winge-ing and wimping about the temperatures and windchills in Regina, where I'm living this year. Over the past month or so, temperatures here have often been in the -20s(C), and this winter we have had far too many days with lows in the -30s. Windchill measures have been even lower.
While Regina consistently has lower winter air temperatures than Chicago, when it comes to windchill records, Chicago "wins" hands down: -64C in Chicago  vs. only -59.2C in Regina .
There's a reason they call Chicago "The Windy City"!