Chicago Songs Ranked
Chicago is an American rock band formed in 1967 in Chicago, Illinois, calling themselves the Chicago Transit Authority in 1968 before shortening the name in 1969. The self-described “rock and roll band with horns” blended elements of classical music, jazz, R&B, and pop music. They began writing songs with politically charged lyrics, and later moved to a softer sound, generating several hit ballads. The group had a steady stream of hits throughout the 1970s and 1980s. In September 2008, Billboard ranked Chicago at number thirteen in a list of the top 100 artists of all time for Hot 100 singles chart success and ranked them at number fifteen on the same list produced in October 2015. Billboard also ranked Chicago ninth on the list of the 100 greatest artists of all time in terms of Billboard 200 album chart success in October 2015. Chicago is one of the longest-running and most successful rock groups, and one of the world’s best-selling groups of all time, having sold more than 100 million records. In 1971, Chicago was the first rock act to sell out Carnegie Hall for a week. o date, Chicago has sold over 40 million units in the U.S., with 23 gold, 18 platinum, and eight multi-platinum albums. They have had five consecutive number-one albums on the Billboard 200 and 20 top-ten singles on the Billboard Hot 100. In 1974 the group had seven albums, its entire catalog at the time, on the Billboard 200 simultaneously. The group has received ten Grammy Award nominations, winning one for the song, “If You Leave Me Now.”The group’s first album, Chicago Transit Authority, released in 1969, was inducted into the Grammy Hall of Fame in 2014. Chicago was inducted into the Rock and Roll Hall of Fame in 2016. In 2017, Peter Cetera, Robert Lamm, and James Pankow were elected to the Songwriters Hall of Fame for their songwriting efforts as members of the music group. Chicago will receive a Grammy Lifetime Achievement Award in 2020. Here are all of Chicago songs ranked.
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20. Ballet for a Girl in Buchannon (The Box, 2003)
“My favorite song as a senior in high school in 1975. The 70’s were amazing years and for music too. I always remember good times when I hear this song. Thank you Chicago for never retiring.”
19. Colour My World (Chicago, 1970)
“This song is the most inspirational out there to everyone in some many ways: The lyrics, the guitar riffs and chords, the tune and beat, the rhythm, the tempo, the drums, bass, the voice and many other more.”
18. We Can Last Forever (Chicago 19 (Expanded Edition), 1988)
“My favorite song of all time. This song brings up so many memories, I get goosebumps every time I listen to it. It’s the only song I can keep on repeat all day/all night and never get bored of it.”
17. Dialogue Parts 1 & 2 (Call on Me (Live), 2019)
“This is a very important song, musically and socially. Nothing demonstrates more vividly the danger of being uninformed. Just incredible! So amazing! The songwriting, the arrangement, the vocals… perfect!”
16. Hard Habit to Break (Chicago 17, 1984)
“My favorite song of all time… Whenever I listen to this song; I must stop doing whatever I am doing because it takes me away to a better place. A song whose vocals and instrumentals will hit anyone with a heart deep in their soul.”
See more: Chicago Albums Ranked
15. What Kind of Man Would I Be? (Chicago 19 (Expanded Edition), 1988)
“This is a beautiful and upbeat song. I get shivers whenever I listen to it. Just incredible! So amazing! The songwriting, the arrangement, the vocals… perfect! Best song Chicago has ever done.”
14. Will You Still Love Me? (Chicago 18 (Expanded Edition), 1986)
“My favorite Chicago song, followed by Hard Habit to Break. Great band. Greatest Chicago’s song. Most underrated song ever. The trademark song of Jason Scheff… a great love song”
13. Just You N’ Me (Chicago VI, 1973)
“Extremely catchy. The bass line is so pretty, and the song rocks up at the end. Such a meaningful and thought-provoking song. Perhaps my favorite Chicago song (along with Saturday in the Park).”
12. Stay the Night (Chicago 17, 1984)
“This song’s lyrics are so powerful and heartfelt. It doesn’t get better than this as far as I’m concerned. I could sit and listen to this song all day because it really speaks to me and almost everyone can relate to it in one way or another.”
11. (I’ve Been) Searchin’ So Long (Chicago VII, 1974)
“This song deserves to be WAY at the top of this list. This song and melody are one of rock’s all-time greats–way better than their later stuff that was too sweet or just boring or dumb lyrics. Extremely catchy. The bass line is so pretty, and the song rocks up at the end.”
10. Does Anybody Really Know What Time It Is? (The Chicago Transit Authority, 1969)
“Absolutely Chicago’s best all-time hit. Kath was completely remarkable on vocals and guitar. Every time I listen to this song, I’m completely awestruck by how awesome Terry Kath’s voice is. Magnificent metals should be higher on the list!”
9. Make Me Smile (Chicago, 1970)
“If someone came to me and asked, “what was the big deal about Chicago? ,” I’d refer them to this song. I almost can’t believe a human-composed this. It’s truly remarkable. Love the ending climax and has to be at least #2 no question. What a combination of harmonic vocals, and crashing horns, and percussion…Damn this is so good.”
8. Feelin’ Stronger Every Day (Chicago VI, 1973)
“There is something unique about this song. It makes you feel so good. It’s just brilliant. Major pick me up song. A real feel-good Great all-around, toe-tapping tune. Great rhythm…fantastic!”
7. Saturday in the Park (Chicago V, 1972)
“It’s an amazing song ahead of its time very modern sounding but at the same time a classic! This is one of the best songs I’ve ever heard, amazing tune! Happy day song! Always lifts my mood to fun times. The classic sound of Chicago”
See more: Dokken Albums Ranked
6. Look Away (Chicago 19, 1988)
“I love this song it always brings me back to my high school love. We tried to stay friends but as it goes after high school we lose touch and then he found someone. It hurt for a while but 33 years later we have reconnected and I am happy to say he will always be my first love and my best friend.”
5. Hard to Say I’m Sorry (Chicago 16, 1982)
“Catchy song, and I love how fast paced it is. Great guitar intro, nice bass intro, and the drumming is so fast, it gives me an actual punk vibe. The lyrics are pretty fun, usually when this band makes love songs, they make them meaningful and relatable.”
4. Beginnings (Chicago Transit Authority, 1969)
“This song’s lyrics are so powerful and heartfelt. It doesn’t get better than this as far as I’m concerned. I could sit and listen to this song all day because it really speaks to me and almost everyone can relate to it in one way or another.”
3. You’re the Inspiration (Chicago 17, 2012)
“True song of the 80s best car ride song, best shower song, and in all best song to listen to no matter what. It’s a true classic Peter Cetera is all anyone needs. Any song is the best, as long as Peter Cetera sang it! He has a silky smooth, dreamy kind of voice!”
2. 25 or 6 to 4 (Chicago, 1970)
“This is a great rock and roll song with the added benefit of a great guitar solo. Clearly their best song. Peter Cetera and Terry Kath best moment together.Iconic song. This is a great rock and roll song with the added benefit of a great guitar solo. Clearly their best song.”
1. If You Leave Me Now (Chicago X, 1976)
“My favorite song of all time. This song brings up so many memories, I get goosebumps every time I listen to it. It’s the only song I can keep on repeat all day/all night and never get bored of it.”
