Best Chicago Songs

Which song by this amazing band do you think deserves the top spot?
The Top Ten
1 25 or 6 to 4

This is a great rock and roll song with the added benefit of a great guitar solo. Clearly their best song.

I've been to over 300 concerts over 40 years. Fans always go crazy waiting for the encore... 25 or 6 to 4!

Number 1. This is the best Chicago song, one of my all-time favorite songs.

2 Beginnings

You young guys don't get what that sound was all about.

Absolutely a classic. Should have been #1.

Gotta be number 1. An oldie but a goodie.

3 If You Leave Me Now
4 You're the Inspiration

Any song is the best as long as Peter Cetera sang it! He has a silky smooth, dreamy kind of voice. I'd say this one is my favorite, with "Feeling Stronger Every Day" as a close second.

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.

I loved this song! It was perfect!

5 Look Away

Even though I don't like the '80s era of the band for the most part, Chicago 19 was a virtual improvement over its predecessor. It was one of my introductions to the band as a young kid in the late '90s.

My favorite songs off that album would have to be "You're Not Alone," "Heart in Pieces," and "What Kind of Man Would I Be?" Don't forget this song as well. I also liked Chicago XXX, Stone of Sisyphus, Now, and Born for This Moment.

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 lost touch. Then he found someone. It hurt for a while, but 33 years later we have reconnected. I am happy to say he will always be my first love and my best friend.

6 Hard to Say I'm Sorry

This song should definitely be in their top 5, maybe top 3, behind If You Leave Me Now and 25 or 6 to 4.

I cannot believe this song isn't on the list. This is their best song by a longshot!

This song is the number one of the band. Why is it so low in position?

7 (I've Been) Searchin' So Long

The same album also marks the grand debut of Brazilian percussionist Laudir de Oliveira, who joined the group in 1973 as a session musician and played on both Chicago VI and VII. It's on the latter album where he makes a strong first impression. "Byblos" is one of my favorite early tracks by the group for a lot of reasons. The Latin/West African vibe is prevalent throughout this track, like something you'd hear on a bossa nova album - Antonio Carlos Jobim would have been proud.

Terry Kath gives a laid-back performance here, and it all just works. It's like walking under a moonlit tropical shore, with passion and soul oozing out of this track.

8 Feelin' Stronger Every Day

There is something unique about this song. It makes you feel so good. It's just brilliant.

This is just a great pick-me-up song! It really revs you up! Love the change in tempo!

No one can match the voice of Peter Cetera!

9 Saturday in the Park

Am I the only one who considers Robert Lamm to be my favorite member of the group? I get that Cetera and Kath (and Champlin much later) have their fans, but I kind of like how Lamm had such a way with words as a songwriter and lyricist. This song is probably a shining example of his skill.

"Darlin' Dear," "Skinny Boy," "Harry Truman," and "Take Me Back to Chicago" are a few other Lamm-penned songs I liked on the albums following Chicago V. He once described Guercio's Caribou Ranch as a "creative monastery" in a 1973 interview. I guess that claim resonates through when listening to a lot of his songs.

10 Does Anybody Really Know What Time It Is?

Magnificent melody. Should be higher on the list!

The Contenders
11 Make Me Smile

This was the peak of the band. In fact, their entire second album is magnificent, in my opinion. It is way better than the stuff they made in the '80s. It had a sort of progressive rock feel to it, and this song is a perfect example.

The album version of the song is divided into two parts, and that's what makes it special. Don't forget Terry Kath's soulful vocals. This pretty much showed their potential as a great '70s rock group.

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.

12 Just You N' Me

Perhaps my favorite Chicago song, along with Saturday in the Park.

13 Hard Habit to Break

Just incredible! So amazing! The songwriting, the arrangement, the vocals... perfect!

One of the greatest power ballads ever!

14 Wishing You Were Here

Great song. Should be much higher.

15 Ballet for a Girl in Buchannon
16 Stay the Night
17 Colour My World

The song "Colour My World" was my young late husband's and my favorite song. We were 19 and 20 at that time. He was shot and killed by a stranger nine months later. With that being said, "Colour My World" by Chicago still remains my favorite song.

18 Old Days

OK, "CBT" memes aside, this is still a vastly underappreciated tune from the band. I feel like Chicago VIII is pretty much the black sheep among their other classic releases. However, it does have some great hidden gems, such as "Brand New Love Affair," "Oh Thank You Great Spirit" (a tribute to Jimi Hendrix), "Hideaway," "Ain't It Blue?" and many others.

My favorite song as a senior in high school in 1975. The '70s were amazing years for music. I always remember good times when I hear this song. Thank you, Chicago, for never retiring.

19 Will You Still Love Me?

My favorite Chicago song, followed by Hard Habit to Break. Great band.

Greatest Chicago song. Most underrated song ever.

20 Dialogue Parts 1 & 2

Not gonna lie, this is an underrated tune from the band. The chemistry between Cetera and Kath is enough to sell it, and it never fails to make me happy. Don't forget the vocal harmonies on the final part of the song (We can make it happen, yeah!). This shows that early '70s Chicago was really ambitious with their eargasmy tunes.

This is a very important song, musically and socially. Nothing demonstrates more vividly the danger of being uninformed.

Even though 25 or 6 to 4 is my favorite song of all time, I'm adding this because it's too awesome to not be included.

21 Street Player
22 What Kind of Man Would I Be?

This is a beautiful and upbeat song. I get shivers whenever I listen to it.

23 Call on Me
24 We Can Last Forever
25 Questions 67 and 68
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