Windy City Rubber Duck Derby July 22, 2014 For the past few years, I have attended the Windy City Rubber Duck Derby here in Chicago. For those of you who haven’t been to the Rubber Duck Derby you can go on Thursday, August 7th. The event is held every year to benefit the Special Olympics of Illinois. Since 1968 the organization has been helping people with intellectual disabilities, and there are over 22,000 athletes who participate in this program.