First recorded by The Bay Harbor Society Orchestra (1922).
Hit version by Frank Sinatra (1958).
From the wiki: “‘Chicago’ is a popular song written by Fred Fisher, and first published in 1922 and recorded by The Bay Harbor Society Orchestra. Other early recordings of the song were made by Django Reinhardt (1937), and Earl Hines (1950). ‘Chicago’ was featured in H.C. Potter’s 1939 film, The Story of Vernon and Irene Castle, starring Ginger Rogers and Fred Astaire. It was later performed by Sinatra in the 1957 movie, The Joker Is Wild, and recorded for Sinatra’s 1958 album Come Fly with Me. Other popular versions of ‘Chicago’ were also recorded by Tony Bennett, Rosemary Clooney, and The Dudley Moore Trio.”
Django Reinhardt with Stephane Grappelli, “Chicago (That Toddlin’ Town)” 1937:
Frank Sinatra, “Chicago” (1958):
The Dudley Moore Trio, “Chicago” (1962):