I have not done St.Louis. Chicago has a permit system, you get it on the spot at City Hall. It used to be 50$, but I heard they raised the price. They have a tower where a lot of buskers work, Grant Park with the famous fountain, near the boat-rides on the water behind Grant Park. You can work with this permit at festivals in Grant Park, but it is a very unpleasant system of getting spots every 2 hours and cops are in charge of buskers, so it sucks royally - but money is very good.
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