I'm starting to investigate costs & requirements for playing music on the Chicago city streets and it's not cheap. Not only is it $100 for a license, but there are noise ordinances and fines of $300+ for playing too loudly in certain areas on Michigan Ave in the evening.
Chicago Street Performer
License Information
A Street Performer License is required to perform in a public area. No amplified music is allowed.
Fee: $100
Municipal Code Reference: 4-268
Inspections: None