Chicago Winter Weather 2024. November 2024 to october 2025 winter will be warmer than normal in the east and colder than normal in the west, with the coldest periods in early and late november, in early december, from late january into early february, and from. Last year, chicago saw the fourth warmest winter on record.

A shift in chicago’s weather is observed as november turns into december, with the average high temperature reducing from a frosty 46°f (7.8°c) to a cold 35.8°f (2.1°c). For the chicago area, the outlook.