November in Chicago is the windiest month of the year. In November, the weather in Chicago is typically cold. Average daily high temperature in November is about 9 degrees above zero. On average, Chicago has 9 partly cloudy, 8 sunny, 7 rainy, and 6 cloudy days in November. The rains are usually moderate. November as well as January, February, March, and April is considered the most uncomfortable time to visit Chicago.