RAG MusicWorld Ranking
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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.

Chicago Popular Songs Ranking [2026] (1–10)

You are everything.CHICAGO8rank/position

Chicago – You’re The Inspiration (Lyrics)
You are everything.CHICAGO

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.

CELL BLOCK TANGOChicago (2002 film)9rank/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.

Still Love MeCHICAGO10rank/position

Chicago – Will You Still Love Me? (Official Music Video)
Still Love MeCHICAGO

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.”

Chicago Popular Song Rankings [2026] (11–20)

Colour my worldCHICAGO11rank/position

Colour My World (2002 Remaster)
Colour my worldCHICAGO

A song written by Chicago trombone player James Pankow in honor of his first love.

The band’s saxophonist, Walter Parazaider, plays flute on this track.

It is one of their most popular songs.

I can’t be honestCHICAGO12rank/position

Chicago – Hard To Say I’m Sorry (Official Music Video)
I can’t be honestCHICAGO

Chicago, which was often played by request on wired broadcasting.

When I hear this song, it reminds me of the streets of Tokyo in the 80s.

I suppose that’s because stylish, urban songs were popular back then.

If you try singing it all the way through while reminiscing about those days, you might feel like you’ve time-traveled.

If She Would Have Been FaithfulCHICAGO13rank/position

Lyrics to If She Would Have Been Faithful by Chicago
If She Would Have Been FaithfulCHICAGO

A venerable American rock band formed in 1967.

Realizing that the woman he loved had betrayed him, he still shrugs it off, saying he’s glad he could know true love—an anthem that captures a man’s pure-heartedness and pride.

The transparent, shimmering sound and harmonies are refreshingly crisp.

Sophisticated LadyCHICAGO14rank/position

Chicago–“Sophisticated Lady”.flv
Sophisticated LadyCHICAGO

When it comes to Chicago, it’s really frustrating that “Hard to Say I’m Sorry” is so famous that their other songs get buried.

I’m sure I’m not the only Chicago fan who wishes more of their stylish tracks would get the spotlight.