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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 Song Rankings [2026] (11–20)

Hard habit to breakCHICAGO15rank/position

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.

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Look AwayCHICAGO16rank/position

Chicago is an American band with a long and proud history.

This work was their most commercially successful single.

Released as a single in 1988, it was also included on that year’s album Chicago 19.

The lyrics portray the narrator’s honest feelings upon hearing from a former lover that they have found someone new.

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Saturday in the ParkCHICAGO17rank/position

Chicago – Saturday In The Park (1973)
Saturday in the ParkCHICAGO

Chicago’s 1972 hit is still often heard on TV and radio in Japan.

When it comes to Chicago, I think “Hard to Say I’m Sorry” is the famous one, but for karaoke, “Saturday in the Park” is easier to sing.

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Street PlayerCHICAGO18rank/position

Street Player (2003 Remaster)
Street PlayerCHICAGO

Chicago’s “Street Player,” often heard in DJ sets and covers, has all the most satisfying elements of disco: a tightly chopped guitar riff and quick, driving beats.

The tonal palette and soaring vocals lend it a distinctly urban feel.

It’s an exceptional dance track you can lose yourself in.

Itō Yūta
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Questions 67 And 68CHICAGO19rank/position

Questions 67 and 68 (2002 Remaster)
Questions 67 And 68CHICAGO

Included on the 1969 album “Chicago Transit Authority.” An 11-member rock band formed in 1967 from Chicago.

This single is from their debut album, released during the period when they were performing under the name Chicago Transit Authority.

You can hear the horns that later became characteristic of their so-called “brass rock” sound.

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