Before the rock and roll band formed as Chicago, they were called The Big Thing, and they were making covers of popular songs.

The group members, James Pankow, Walter Parazaider, Lee Loughnane, and Robert Lamm, remained together over 50 years.

They had an interesting style for naming their albums as they named every album of theirs with roman numbers (Such as Chicago I, Chicago III) besides their second album, which was simply named: Chicago. Let’s take a look at their top ten hits!

#10. Chasin’ The Wind

The rock song is about an unanswered love that feels like chasin’ the wind at the end of the day when something never begins. There can’t be an end.

#9. You’re Not Alone

The song is a touching yet emotive song that is mentioning someone who feels alone, but the group says you are not alone!

#8. If You Leave Me Now

It is one of the band’s biggest hits co-written by Terry Kath and Robert Lamm. The song brought the band a Grammy award for “Best Pop Vocal Performance By a Duo, Group Or Chorus.”

#7. Stay The Night

The song is about asking a woman to stay for a passionate night, which has fiery lyrics. At the music video, we see a woman rejecting the band member while driving her car away.

#6. I Don’t Wanna Live Without Your Love

The song was recorded for the album, Chicago IX. It is about the feelings after a break-up that the writer feels absent without her love.

#5. Will You Still Love Me?

The song directly hit the charts of the time. It was also covered by the Jazz group Urban nights. It also became a special wedding song with romantic lyrics.

#4. 25 or 6 to 4

The song was written by Lamm. The meaning of the title of the song is about the time of day: either 3:35 a.m. (25 to 4) or 3:34 a.m. (26 to 4). It was about the time that he was trying to write the song as he was watching the sky and waiting for the inspiration to come.

#3. Look Away

The song tells us a story about a woman and a man who remained friends when they break-up, however, when she had another person in her life it became hard for him as the song refers: Don’t look at me, I don’t want you to see me this way.

#2. Hard To Say I’m Sorry/Get Away

Peter Catera and producer David Foster co-wrote the song. It won an ASCAP Pop Music Award for “Most Performed Songs.” This soft-rock song became a hit of the time. There are ups and downs in every relationship. This song is about these downtimes.

#1. You’re the Inspiration

The song is a celebration of finding the right person who became an inspiration. It is mentioning a big love that meant to be forever. It was one of the biggest hits of the ’80s and ’90s.

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I am an avid Mac-user, nerd, musician, freelancer, and gamer. Ask me about my collection of M:TG cards! I've also got a horrible habit of needing the absolute newest technological wonder, whether it's stable or not. If they made a home-version of the LHC, I'd have 2. Additionally, I've been playing music for the better part of 14 years. I'm self-taught on piano, guitar, trumpet, trombone, sax, clarinet, bass, drums and other percussion, and around 10 other instruments. I also spend quite a bit of time dabbling in synthesizers, sequencers, and samplers. I'm also founder of Quotelicious where I collect and share the quotes I love.


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