CHICAGO Popular Song Rankings [2026]

Colour my worldCHICAGO11rank/position

Colour My World (2002 Remaster)

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)

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

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

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.

Hard habit to breakCHICAGO15rank/position

Hard Habit to Break

Chicago is a long-running American rock band from Chicago that has been active for many years.

Their 1984 song “Hard Habit to Break” is known in Japan as “Wasurenu Kimi ni.” It is included on their album Chicago 17.