January in Milwaukee is the snowiest, the cloudiest, and the most freezing month of the year. In January, the weather in Milwaukee is typically freezing. Average daily high temperature in January is about 1 degree below zero. On average, Milwaukee has 11 partly cloudy, 8 cloudy, 6 sunny, 5 snowy, and 1 rainy day in January. The snowfalls are usually moderate. January as well as February, March, April, and May is considered the most uncomfortable time to visit Milwaukee.