Best Chicago Songs

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

The Top Ten

1 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

Just too good!

V 5 Comments
2 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

25 or 6 to 4 would be the cliche pick for number 1 so I’m pleasantly surprised that this beautiful timeless piece of music is number 1

V 3 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.

I got my girlfriend with this song,Great song

V 1 Comment
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 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
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 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...

8 Stay the Night
9 Feelin' Stronger Every Day

Major pick me up song. A real feel good

Great all-around, toe-tapping tune.

#2, such an energetic song, great rock, great tune

10 Does Anybody Really Know What Time It Is?

Terrific song

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 Will You Still Love Me?

Should be top 10

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

13 (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.

14 Hard Habit to Break

Best song Chicago has ever done - Liam31idents

V 2 Comments
15 Just You N' Me
16 What Kind of Man Would I Be?
17 Colour My World

Great, classic slow song.

Best make out song ever!

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 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.

20 Questions 67 and 68

Such great voice range

21 Love Me Tomorrow
22 Call on Me
23 Ballet for a Girl in Buchannon
24 Wishing You Were Here

Great song, should be much higher.

25 A Hit by Varese
26 Now
27 No Tell Lover

A good one from the early days.

28 Baby, What a Big Surprise
29 I Don't Wanna Live Without Your Love
30 We Can Last Forever
31 Lowdown
32 Alive Again
33 Wake Up Sunshine!
34 You're Not Alone
35 Street Player
36 Once In a Lifetime

Great uplifting Chicago song.

37 Listen
38 Little One
39 What's This World Coming To
40 Free
41 Manipulation
42 Along Comes a Woman

Amazing underrated song

43 Prima Donna
44 Song for You

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

45 Fancy Colours
46 I’m a Man
47 Harry Truman
48 Another Rainy Day in New York City
49 Brand New Love Affair
50 Take Me Back to Chicago
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List Stats

600 votes
51 listings
7 years, 105 days old

Top Remixes (5)

1. You're the Inspiration
2. If You Leave Me Now
3. Stay the Night
Yaya2010
1. Look Away
2. Hard to Say I'm Sorry
3. Will You Still Love Me?
bigbubba2001
1. Feelin' Stronger Every Day
2. (I've Been) Searchin' So Long
3. 25 or 6 to 4
Billyv

WRemix
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