This route follows the course of the 1895 Chicago Times-Herald Race, which was the first automobile race held in the United States (https://en.wikipedia.org/wiki/Chicago_Times-Herald_race). The winner of that race finished in 7 hours and 53 minutes of running time, and 10 hours and 23 minutes of elapsed time, which makes an interesting and realistic comparison point for present day runners on this route.
See full route description here: https://medium.com/south-side-runs/the-2020-chicago-comrades-a-90-km-run-through-chicago-f658d2faf461
This is a YouTube video of the route of the route originator's second run in 2021: https://www.youtube.com/watch?v=h4ce1S4HPcQ
The route starts and ends at 60th and Cornell.