The single topped the Billboard Hot 100 on October 23, 1976, and stayed there for two weeks, making it the first number one hit for the group.

[19][20][21] Peter Cetera originally wrote "If You Leave Me Now" at the same time as Chicago VII's "Wishing You Were Here", and composed it on a guitar.

[23] Band manager James William Guercio initially played acoustic guitar on the demo version of the track, figuring that regular guitarist Terry Kath would record the proper part when he was in the studio next.

[24] Walter Parazaider recalled that he heard the song on the radio while cleaning his pool and initially thought "it sounded like McCartney," not realizing it was his own band's work.

[10] In the same vein, the single, "If You Leave Me Now", was depicted as a chocolate "kiss" from the album in a full-page advertisement in Cash Box magazine.

"[29] Upon the group's induction into the Rock and Roll Hall of Fame in 2016, entertainment and pop culture writer Troy L. Smith included "If You Leave Me Now" in his list of seven Chicago songs that "kill any doubt about their candidacy", and said, "... it's a key contributor to the band's fame and, thus, its Rock Hall induction.

Chicago Additional personnel In 1992, German music group Chess covered the song which achieved modest success.

In the HBO miniseries, The Regime, the dictator portrayed by Kate Winslet sings a "cringy" rendition of "If You Leave Me Now" in the initial episode which first aired on March 3, 2024.

So it seemed like the right song to mine for a ridiculous moment at the top of the show,” but one that also becomes “strangely poignant” by the series’ end.