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 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.

Peter Cetera and Terry Kath best moment together.Iconic song

Been to over 300 concerts over 40 years, always fans 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 If You Leave Me Now If You Leave Me Now

Great song - Camaro6

Love this song

Peter Cetera the best singer of all time

Peter Cetera vocals and writing need I say more

3 You're the Inspiration You're the Inspiration


Peter Cetera is all anyone needs

25 or 6 to 4 is my favorite, but this has got to be second best!

I loved this song! It was perfect!

4 Hard to Say I'm Sorry

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

I gave it a vote just so I could say YUK, stupid, vapid lyrics...

This Song is the number one of band, Why so below position?

This song is the number 1 how come is in the 17th?

5 Look Away

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...

6 Saturday in the Park

The classic sound of Chicago

This is one the best songs I've ever heard, amazing tune!

How is this song not in at least the top 5?! It's an amazing song ahead of its time very modern sounding but at the same time a classic!

How can anything from the good old jazz-fusion era not be #1, especially this ode to good times in the summertime?

7 Make Me Smile

# 1 no contest

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.

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.

Absolutely Chicago's best all time hit. Kath was completely remarkable on vocals and guitar.

8 Feelin' Stronger Every Day

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

No one can match the voice of Peter Cetera!

Don Barnes/38 Special does a great cover of this song - Jukeboxhero

Major pick me up song. A real feel good

9 Does Anybody Really Know What Time It Is?

Chicago: Does anybody really know what time it is?
Me: 25 or 6 to 4 - scienceLover10

Magnificent metals, should be higher on the list!

Terrific song

10 Stay the Night

So Slow, yet so powerful!

The Contenders

11 Beginnings

First and Best Chicago Song I ever heard, Brings back the memories

Best song ever!

Best of the Best

Gotta be number 1. An oldie but a goodie.

12 (I've Been) Searchin' So Long

The most beautiful song from Chicago.

This song should easily be in the top 3.

Before Peter cetera got cheezy.

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.

13 Hard Habit to Break

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

One of the greatest power ballads ever!

Catchy n one of their best songs with hard to say I'm sorry

Best song Chicago has ever done - Liam31idents

14 Will You Still Love Me?

Greatest Chicago's song. Most underrated song ever.

You know who its for

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

Should be top 10

1 Comment
15 Just You N' Me

Their best song ever,

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

16 What Kind of Man Would I Be?

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

17 Love Me Tomorrow
18 Colour My World

Best slow dance song ever.

Great, classic slow song.

Best make out song ever!

19 Old Days

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.

Magnificent composition

20 Along Comes a Woman

Great song.

Amazing underrated song

21 Dialogue Parts 1 & 2

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.

22 Questions 67 and 68

Peter Cetera, what a voice

Such great voice range

23 Ballet for a Girl in Buchannon

Terry Kath
That's all there is to say

24 Call on Me
25 Wishing You Were Here

Great song, should be much higher.

26 A Hit by Varese
27 I’m a Man

Amazing. One of my top 3 Chicago songs along with Feelin' Stronger and 25 or 6 to 4.

Love this song

Terry Kath doesn’t stop in this! Rip the best

28 I Don't Wanna Live Without Your Love

Haunting simplicity of a perfectly constructed classic rock song, around a familiar theme - the angst of the heart.

29 Baby, What a Big Surprise
30 Now

Love the rhythm of this song and Jason does an awesome job! One of my favorites!

31 No Tell Lover

A good one from the early days.

32 Street Player
33 We Can Last Forever
34 Brand New Love Affair
35 Alive Again

Brings back such happy memories. Love the melody of the chorus line.

36 Prima Donna
37 Song for You

I can't believe this song isn't on the list..

38 Lowdown
39 What's This World Coming To

Fantastic song, for many reasons. Fun to play drums to.

Fantastic upbeat song! This HAS to be up on the list!

40 Wake Up Sunshine!
41 You're Not Alone
42 Once In a Lifetime

Great uplifting Chicago song.

43 Listen
44 Another Rainy Day in New York City
45 Little One
46 You are on My Mind
47 Free
48 Manipulation
49 Fancy Colours
50 Harry Truman
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List Stats

1,000 votes
52 listings
8 years, 314 days old

Top Remixes (6)

1. You're the Inspiration
2. If You Leave Me Now
3. Stay the Night
1. Look Away
2. Hard to Say I'm Sorry
3. You're the Inspiration
1. Feelin' Stronger Every Day
2. (I've Been) Searchin' So Long
3. 25 or 6 to 4

View All 6

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