How common is it for the temperature in January to never rise above freezing for the entire month?
It is extremely rare. Chicago climatologist, Frank Wachowski, reported that dating back to 1871, January 1977 is the only month where the mercury failed to reach the freezing mark, the highest reading for the month, just 30 degrees on the 24th. That month, comprised the major part of a record 43-day below freezing stretch that extended from Dec. 28-Feb. 8. The only other January that came close was January, 1918 with just one day that reached or topped freezing, Jan. 25, with a high of 35. That month also featured two days with highs of 31, Jan. 5 and 24.