CHICAGO Popular Song Rankings [2026]

Hard To Say I’m SorryCHICAGO1rank/position

Chicago – Hard To Say I’m Sorry (Official Music Video)

This is a signature work by Chicago, the American brass rock band, depicting the pain of heartbreak alongside an elegant piano melody.

Released in September 1982 and produced by David Foster, the piece elevates the rich musicality of the brass section into a pop-oriented arrangement, spending two consecutive weeks at No.

1 on the U.S.

singles chart.

It was used as the ending theme for the film “Summer Lovers” and became familiar in Japan as a commercial song for Osaka Gas and Toyota.

The lyrics portray a man who, after being told goodbye by his girlfriend, regrets his past behavior—feelings many listeners can surely relate to.

You’re the InspirationCHICAGO2rank/position

Chicago – You’re the Inspiration (Official Music Video)

Chicago, the rock band known to all, delivers a gem of a ballad tenderly wrapped in everlasting love and gratitude.

Its refreshing piano tones and warmly resonant melody line stir emotions that bring a lump to your throat.

Released in October 1984 and reaching No.

3 on the U.S.

Billboard chart the following January, this major hit appears on the album Chicago 17.

It gracefully weaves deep feelings and appreciation for a loved one, celebrating the wonder of fateful love.

Perfect for making life’s important moments even more memorable, it’s a popular choice for special occasions—such as a first dance at a wedding.

Saturday in the ParkCHICAGO3rank/position

Chicago – Saturday in the Park (Official Audio)

This song, used in a 2001 Toyota Brevis commercial, is by the American rock band Chicago.

Speaking of Chicago, they’re a rock band known for incorporating a horn section into their lineup.

In this track, you can enjoy a bright brass sound right from the intro, and the clean vocals add to it, making it a song that lifts your spirits as you listen.

It’s included on their 1972 album Chicago V.

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Hane Keisuke

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Will You Still Love Me?CHICAGO4rank/position

Chicago- Will You Still Love Me? (Music Video)

Included on the 1986 album “Chicago 18.” A rock band from Chicago formed in 1967.

This is a single cut from the first album released after Peter Cetera’s departure.

The sweet vocals singing of his love for her are wonderful, and the ensemble with the chorus is beautiful as well.

Does Anybody Really Know What Time It Is?CHICAGO5rank/position

Chicago Transit Authority – Does Anybody Really Know What Time It Is?

“Does Anybody Really Know What Time It Is?” is a song by the American rock band Chicago.

Even among Chicago’s catalog—as a band emblematic of brass rock and AOR—this track is a bit unusual.

In the uncut album version, it starts with a piano solo featuring mysterious harmonies, then the band comes in and shifts into an intro with an irregular time signature.

Once the vocals enter, you can enjoy the quintessential Chicago sound.

It’s a curious track, but definitely give it a listen!

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Hamada Takuya

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If You Leave Me NowCHICAGO6rank/position

Chicago – If You Leave Me Now (Official Audio)

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 windCHICAGO7rank/position

Chasing the wind by Chicago LYRICS

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.