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rock The Best Chicago Songs of All Time  

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1.6k votes 222 voters 3.4k views

List Rules Vote for your favorite Chicago songs, not just singles and hits.

List of the best Chicago songs, ranked by fans like you. After first finding success in the late-'60s, this best-selling soft rock outfit went on to have decades of staying-power. They differentiated themselves from their peers by relying heavily on horn arrangements. This list includes every major Chicago single, from "If You Leave Me Now" to "25 or 6 to 4," but true fans know there are other great songs to vote on besides the radio hits. Music videos and lyric videos are included next to each song name, so if you haven't heard a track you can listen to it right here on this page.

Is one of your favorite Chicago songs missing from this poll? Add it to the list so it has a chance to rise to the top. If the order of this list bothers you, then stand up and do something about it by creating your own version and re-ranking it. Simply click the "Rerank List" button and you can put the songs in whatever order you like.

1
59 14
Ranker Video

2
47 12
Ranker Video

3
55 21
Ranker Video

4
50 21
Ranker Video
Hard Habit to Break Chicago 17, The Ultimate Chicago: Australian Tour Edition

5
35 11
Ranker Video
Love Me Tomorrow Chicago 16

6
39 15
Ranker Video

7
36 13
Ranker Video
Along Comes a Woman Chicago 17

8
34 13
Ranker Video
Colour My World Chicago II

9
57 34
Ranker Video
25 or 6 to 4 Chicago II

10
34 16
Ranker Video

11
29 12
Ranker Video
Just You 'N' Me Chicago VI

12
32 15
Ranker Video
Stay the Night Chicago 17

13
33 17
Ranker Video
Old Days Chicago VIII

14
41 24
Ranker Video

The Sexiest Women in Rock History, Ranked

15
27 12
Ranker Video
(I've Been) Searchin' So Long Chicago VII, The Ultimate Chicago: Australian Tour Edition

16
43 27
Ranker Video
Does Anybody Really Know What Time It Is? Chicago Transit Authority

17
20 7
Ranker Video
Poem 58 Chicago Transit Authority

18
30 17
Ranker Video
Beginnings Chicago Transit Authority

19
27 15
Ranker Video
Questions 67 and 68 Chicago Transit Authority

20
39 26
Ranker Video
Saturday In The Park Chicago V, The Ultimate Chicago: Australian Tour Edition

21
13 3
Ranker Video
Happy Man Chicago VII

The Best Rock Vocalists

22
29 18
Ranker Video
Make Me Smile Chicago II

23
26 16
Ranker Video
Look Away Chicago 19

24
22 13
Ranker Video
I'm a Man Chicago Transit Authority

25
25 16
Ranker Video

26
12 4
Ranker Video
Call on Me Chicago VII

27
13 5
Ranker Video
Listen Chicago Transit Authority

28
11 4
Ranker Video
No Tell Lover Hot Streets

18 Pictures of Taylor Swift Not Wearing Makeup

29
9 3
Ranker Video
Fancy Colours Chicago II

30
10 4
Ranker Video
Wake Up Sunshine Chicago II

31
14 8
Ranker Video

32
15 9
Ranker Video

33
9 4
Ranker Video
Free Chicago III

34
9 5
Ranker Video

35
8 4
Ranker Video
Alive Again Hot Streets, The Ultimate Chicago: Australian Tour Edition

The Greatest Songs by One-Hit Wonders

36
5 1
Ranker Video
Movin In' Chicago II

37
9 6
Ranker Video

38
8 5
Ranker Video
Free Form Guitar Chicago Transit Authority

39
8 5
Ranker Video
Street Player Chicago 13

40
7 4
Ranker Video
Southern California Purples Chicago Transit Authority

41
6 3
Ranker Video
Liberation Chicago Transit Authority

42
8 6
Ranker Video
We Can Last Forever Chicago 19

List of Famous Astronauts

43
7 5
Ranker Video

44
4 2
Ranker Video
Lowdown Chicago III

45
5 4
Ranker Video
In the Country Chicago II

46
5 4
Ranker Video
The Road Chicago II

47
4 3
Ranker Video
Poem for the People Chicago II

48
1 0
Ranker Video
1yoohoo added Dialogue Part 1 & 2 Chicago V

49
1 0
Ranker Video

50
1 0
Ranker Video
1yoohoo added Harry Truman Chicago VIII