I’m puzzled by the comments throughout this thread about us “blowing it with railroad” and “thinking water would work for transportation”. This is simply not true.

We had railroads. We had some of the best and most innovative lines in the country. Our location was the issue. Chicago is on the parallel with NY and San Fran, which were THE cities people wanted to connect back in the day.

Not saying we have been forward thinking at all with regards to mass transit in recent times, but we can and did invest in railroads when we were lapped by many of the cities that took off in the pre WWI era. We were a victim of our location, as were many other river cities that peaked in the early to mid afternoon 1800s.