Best Chicago Songs

Which song by this amazing band do you think deserves the top spot?

The Top Ten

1 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

V 7 Comments
2 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

Just too good!

Been to over 300 concerts over 40 years, always fans go crazy waiting for the encore...25 or 6 to 4!

V 7 Comments
3 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!

V 4 Comments
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?

V 2 Comments
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 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.

V 3 Comments
7 Feelin' Stronger Every Day

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

Great rhythm...fantastic!

Major pick me up song. A real feel good

Great all-around, toe-tapping tune.

V 1 Comment
8 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?

V 3 Comments
9 Does Anybody Really Know What Time It Is?

Magnificent metals, should be higher on the list!

Terrific song

10 Stay the Night

The Contenders

11 Beginnings

Best of the Best

Gotta be number 1. An oldie but a goodie.

This is Chicago's best song, way to low on this list

Absolutely a classic. Should have been #1.

V 4 Comments
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.

V 2 Comments
13 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

V 1 Comment
14 Hard Habit to Break

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

Best song Chicago has ever done - Liam31idents

Best in my opinion

Should be top 10

15 What Kind of Man Would I Be?

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

16 Just You N' Me

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

17 Love Me Tomorrow
18 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

19 Colour My World

Best slow dance song ever.

Great, classic slow song.

Best make out song ever!

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
24 Call on Me
25 A Hit by Varese
26 Wishing You Were Here

Great song, should be much higher.

27 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.

28 Baby, What a Big Surprise
29 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

30 Now
31 No Tell Lover

A good one from the early days.

32 We Can Last Forever
33 Alive Again

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

34 Street Player
35 Song for You

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

36 Lowdown
37 What's This World Coming To

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

38 Wake Up Sunshine!
39 You're Not Alone
40 Once In a Lifetime

Great uplifting Chicago song.

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

900 votes
52 listings
8 years, 133 days old

Top Remixes (5)

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 5

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