I live in Chicago and we have one of the worst recycling rates in the country, even for valuable materials like aluminum. I have read about the Oregon bottle bill which has been successful.
People are barely willing to take their recycling to the alley, I doubt they'll schlep it to a pickup site for free, especially since so many Chicagoans don't have cars or wheelbarrows or bike trailers.
And getting volunteers to sort it? That's another no-sell.
We need solutions, and I'm glad you're thinking about it, but keep thinking.