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

Trevor & Patricia

V 2 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

I lo ve that wahh wahh sound

V 4 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 Make Me Smile

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).

Every time I listen to this song, I'm completely awestruck by how awesome Terry Kath's voice is.

This is one of Chicago's greatest some.I love it

6 Feelin' Stronger Every Day

Major pick me up song. A real feel good

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

Great all-around, toe-tapping tune.

7 Stay the Night
8 (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.

9 Look Away
10 What Kind of Man Would I Be?

The Contenders

11 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.

Love it

V 1 Comment
12 Just You N' Me
13 Does Anybody Really Know What Time It Is?

Terrific song

14 Colour My World

Great, classic slow song.

Best make out song ever!

15 Hard Habit to Break

Best song Chicago has ever done - Liam31idents

V 2 Comments
16 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.

#1 hands down

V 2 Comments
17 Will You Still Love Me?

Should be top 10

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

18 Love Me Tomorrow
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 Questions 67 and 68

Such great voice range

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List Stats

600 votes
49 listings
7 years, 37 days old

Top Remixes

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



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