CHICAGO Popular Song Rankings [2026]
Known as pioneers of brass rock, CHICAGO continue to energetically release new works and tour to this day.
Their style of incorporating brass into rock has influenced many artists in Japan.
With numerous lineup changes and a tumultuous history, we will introduce their most-played songs in a ranked format.
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Chicago Popular Songs Ranking [2026] (1–10)
You are everything.CHICAGO6rank/position
Chicago is a long-lasting group that has been active for over 40 years since their debut in 1969.
They have close to 50 hit songs, and in 2016 they were inducted into the Rock and Roll Hall of Fame.
This song is one of Chicago’s signature ballads—a sweet love song—that reached No.
3 in 1985.
If You Leave Me NowCHICAGO7rank/position
A gem of a love ballad that sings of a sweet yet heartrending farewell.
Dialing back the brass sound synonymous with Chicago, it features a warm, memorable blend of acoustic guitar and strings.
It gently wraps feelings of anxiety and regret over losing someone precious, the desire to hold on, and the inability to let go, in a delicate melody.
Released in July 1976, it topped the charts in countries around the world, including the United States and the United Kingdom, and won two categories at the 1977 Grammy Awards.
Timelessly beloved—featured, for example, on the soundtrack of the video game Grand Theft Auto V—it continues to soothe the hearts of many music fans as a song that stays close in times of parting or romantic turmoil.
Chasing the windCHICAGO8rank/position
Included on the 1991 album “Twenty 1.” An 11-member rock band from Chicago formed in 1967.
Set to a mid-tempo rhythm that conveys a solid rock beat and a softly resonant pop melody, this track features sweet, deeply emotive vocals that are captivating to the ear.
Still Love MeCHICAGO9rank/position
The kings of love songs, Chicago, are absolutely indispensable for wedding songs.
“Will you still love me for the rest of my life?” If a woman is asked, “Will you love me for the rest of my life?” the answer will surely be “Of course.”
CELL BLOCK TANGOChicago (2002 film)10rank/position
Female inmates who killed men for various reasons tell their stories to a tango melody in “Cell Block Tango.” It’s one of the most popular songs in Chicago.
Once you hear those powerful, gritty vocals, this number is guaranteed to stick in your head.