We just ended up experiencing the 5th cloudiest February on record in Chicago dating back to 1893. Our veteran weather observer Frank Wachowski measured just 29% of possible sunshine in February – the least since 1962 when he recorded 21% of possible sunshine that February (the all-time record low).
Chicagoans will have a brief glimpse of sun Friday morning but then clouds will return with a chance of some light snow Friday night as low pressure passes to our north. We will have another chance at snow Saturday night into Sunday–low pressure passing to our south.
Strengthening northerly winds will then bring bitterly cold air into the Midwest and Great Lakes later Sunday – temperatures probably dropping below zero Monday morning with -10 to -20 degree wind chills. The bitter cold will remain Tuesday followed by a gradual moderation the rest of the workweek.