Chicago also reversed the flow of the Chicago River.

https://en.wikipedia.org/wiki/Chicago_River#Reversing_the_fl...

They also rebuilt much of the city because it was wiped out during the Great Chicago Fire of 1871, and now the grid system is one of the most commonsensical ones in any major American city.

Chicago is an example of a (more or less) clean-slate engineered large city -- one that arose as a result of tragedy (fire) and failure (cholera).