Regarding chicago this:
https://en.wikipedia.org/wiki/Double_Cup
Regarding a city that's already done this - Detroit went full LED this year:
http://www.mlive.com/news/detroit/index.ssf/2017/01/led_ligh...
The difference on the ground is quite noticeable, partly because we're so used to sodium yellow and as LEDs are in the 6000K range - i.e. daylight ... it's 'uncanny', things certainly seem more HD - here's a picture I recently took at night:
https://iainmait.land/img/photos/1280/street_crossing_2_2017...