As a city resident for eight years, I still don’t know an authoritative answer on paying for Chicago street fairs as the answer has varied from gatekeeper to gatekeeper:
Can fair organizers require admission for a fair held on public streets or is merely a suggested donation?
I don’t know the formal answer to your question, but I have an anecdotal one. I used to live on Montana street, right off Lincoln. Every summer, during Taste of Lincoln Avenue, I would have to go through the fest to get to my damn apartment! I would just tell the gatekeeper, “Hey, man; I live over there,” and point, and they always let me through.
I’ve been tempted to use that as a gambit for other fairs, but my sense of civic responsibility stops me 
…TRM
Legally it is merely a suggested donation. No requirement to pay.
If memory serves, the guy who runs The Alley off Belmont was making a big deal of this, and even had a banner up a few summers ago. I remember a story in the (dead-tree-edition) Reader.