May in South Milwaukee is the rainiest month of the year. In May, the weather in South Milwaukee is typically warm. Average daily high temperature in May is about 17 degrees above zero. On average, South Milwaukee has 12 rainy, 9 partly cloudy, 8 sunny, and 2 cloudy days in May. The rains are usually heavy. May as well as January, February, March, and April is considered the most uncomfortable time to visit South Milwaukee.