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

25 or 6 to 4 is the best but this song deserves a lot more recognition

This song should be number 1 or number 2 on this list - mneilan

This along with Stairway to Heaven by Led Zeppelin are the only to legendary songs.

Really? What about comfortably numb, bohemian rhapsody, smells like teen spirit, november rain, livin' on a prayer? - Ankon

Love this song

V 6 Comments
2 25 or 6 to 4

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.

Much better song than top 2 listed, my second favorite Chicago tune

Peter Cetera and Terry Kath best moment together.Iconic song

V 6 Comments
3 You're the Inspiration

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

I loved this song! It was perfect!

Best Chicago song.

Any song is the best, as long as Peter Cetera sang it! He has a silky smooth, dreamy kind of voice! But, I’d say this one is my favorite, second being “Feeling Stronger Every Day”

V 3 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?

Top 3 for sure!

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

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.

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

The best quintessential Chicago: vocals, horns and lyrics (and of course Kath).

V 2 Comments
7 Saturday in the Park

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?

Happy day song! Always lifts my mood to fun times.

The classic sound of Chicago

V 3 Comments
8 Feelin' Stronger Every Day

Major pick me up song. A real feel good

Great all-around, toe-tapping tune.

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

Great rhythm...fantastic!

V 1 Comment
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

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

Absolutely a classic. Should have been #1.

Gotta be number 1. An oldie but a goodie.

Anything from 80s not in top 10
this should be top 5

V 3 Comments
12 (I've Been) Searchin' So Long

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.

Such a meaningful and thought provoking song.

Before Peter cetera got cheezy.

V 1 Comment
13 Will You Still Love Me?

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

You know who its for

Should be top 10

The trademark song of Jason Scheff... a great love song

14 Hard Habit to Break

Best song Chicago has ever done - Liam31idents

Best in my opinion

Should be top 10

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

15 Just You N' Me
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 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

Great, classic slow song.

Best slow dance song ever.

Best make out song ever!

20 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.

21 Along Comes a Woman

Amazing underrated song

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 Wishing You Were Here

Great song, should be much higher.

26 A Hit by Varese
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 Now
30 No Tell Lover

A good one from the early days.

31 I’m a Man

Love this song

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

32 We Can Last Forever
33 Lowdown
34 Alive Again
35 What's This World Coming To

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

36 Wake Up Sunshine!
37 You're Not Alone
38 Street Player
39 Once In a Lifetime

Great uplifting Chicago song.

40 Listen
41 Another Rainy Day in New York City
42 Little One
43 You are on My Mind
44 Free
45 Manipulation
46 Prima Donna
47 Song for You

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

48 Fancy Colours
49 Harry Truman
50 Brand New Love Affair
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List Stats

800 votes
51 listings
8 years, 9 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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