It was run annually from 1983 to 2015 at Maywood Park in Melrose Park, Illinois, a suburb of Chicago.
Elimination heats were required to determine the finalists for the main race.
It was the top race of a program that also featured Maywood's other top stakes races — the Abe Lincoln, the Galt and the Cinderella.
A notable running of the Windy City was in 1987, when Bomb Rickles won the final at odds of 190-1.
[1] Maywood park closed that year.