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I've been thinking a lot about what the most-logical next cities would be for congestion-relief pricing and I really think Chicago and Boston are the best options. Both have good metro and regional rail networks, clearly defined CBDs, and logical geographic boundaries.

For Chicago, I think the logical boundaries would be Roosevelt Road to the south and all of the river crossings to the West and North. I'd keep Lake Shore Drive untolled but if you turn off it anywhere between Roosevelt and the River, you're tolled (akin to the West Side Hwy in NYC).

Boston is a bit trickier on the southwest side. I'd like to see Back Bay included in the zone, but including the South End is probably not necessary. So there are three options that I see. Dark blue as the most expansive, teal to include Back Bay, and pink as perhaps as phase 1 with room to grow.