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The Best Chicago Albums of All Time 

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Updated October 13, 2018 2.8k votes 741 voters 23.5k views

List Rules This list includes studio albums only, so if you add an album make sure it's a proper studio release.

Veteran rock band Chicago is one of the best rock bands and best jazz rock bands of all time. List of the best Chicago albums, including pictures of the album covers when available. This Chicago discography is ranked from best to worst, so the top Chicago albums can be found at the top of the list. The band hails from the city of Chicago, and has been together in various formations since 1967. Over time, the group's sound has evolved from rock to soft rock to pop. 

To make it easy for you, we haven't included Chicago singles, EPs, or compilations, so everything you see here should only be studio albums. If you think the greatest Chicago album isn't high enough on the list, then be sure to vote for it so it receives the credit it deserves. Make sure you don't just vote for critically acclaimed albums; if you have a favorite Chicago album, then vote it up, even if it's not necessarily the most popular.

If you want to know the Best Chicago album of all time, this list will answer your questions. It has a variety of albums in it, from Chicago II to The Chicago Transit Authority. This list of popular Chicago CDs has been voted on by music fans around the world, so the order of this list isn't just one person's opinion. 

list ordered by
1
Chicago II is listed (or ranked) 1 on the list The Best Chicago Albums of All Time
By Chicago (1970); Tracks: Now More Than Ever, West Virginia Fantasies & 25 or 6 to 4

Label: Columbia

Genres (Music): Progressive rock, Rock music, Classical music, Jazz, Jazz fusion

2
Chicago Transit Authorit... is listed (or ranked) 2 on the list The Best Chicago Albums of All Time
By Chicago (1969); Tracks: Someday (August 29, 1968) & Introduction

Label: Columbia

Genres (Music): Progressive rock, Rock music, Hard rock, Jazz fusion

More Chicago Transit Authority 

#1,478 of 3,542 The Greatest Albums of All-Time #112 of 623 The Greatest Guitar Rock Albums of All Time #62 of 284 The Best Debut Albums of All Time, Ranked

3
Chicago V is listed (or ranked) 3 on the list The Best Chicago Albums of All Time
By Chicago (1972); Tracks: All Is Well, A Hit by Varèse & Now That You've Gone

Producer: James William Guercio

Length (mins): 00:44:41

Label: Columbia

Genres (Music): Rock music

4
Chicago VII is listed (or ranked) 4 on the list The Best Chicago Albums of All Time
By Chicago (1974); Tracks: Mongonucleosis, Devil's Sweet & Skinny Boy

Producer: James William Guercio

Length (mins): 01:12:34

Label: Columbia

Genres (Music): Rock music, Jazz fusion

5
Chicago VI is listed (or ranked) 5 on the list The Best Chicago Albums of All Time
By Chicago (1973); Tracks: In Terms of Two, Something in This City Changes People & Jenny

Producer: James William Guercio

Length (mins): 00:38:23

Label: Columbia

Genres (Music): Rock music

6
Chicago III is listed (or ranked) 6 on the list The Best Chicago Albums of All Time
By Chicago (1971); Tracks: Once Upon a Time, Man Vs. Man: The End & Sing a Mean Tune Kid

Label: Columbia

Genres (Music): Rock music, Rock and roll, Jazz fusion

7
Chicago X is listed (or ranked) 7 on the list The Best Chicago Albums of All Time
By Chicago (1976); Tracks: You Are on My Mind, Hope for Love & Together Again

Producer: James William Guercio

Label: Columbia

Genres (Music): Rock music, Rock and roll

8
Chicago 17 is listed (or ranked) 8 on the list The Best Chicago Albums of All Time
By Chicago (1984); Tracks: Once in a Lifetime, Remember the Feeling & Prima Donna

Producer: David Foster

Length (mins): 00:41:51

Genres (Music): Rock music, Adult contemporary music, Soft rock

9
Chicago VIII is listed (or ranked) 9 on the list The Best Chicago Albums of All Time
By Chicago (1975); Tracks: Oh, Thank You Great Spirit & Never Been in Love Before

Length (mins): 00:39:35

Label: Columbia

Genres (Music): Rock music, Rock and roll

10
Chicago XI is listed (or ranked) 10 on the list The Best Chicago Albums of All Time
By Chicago (1977); Tracks: The Inner Struggles of a Man, Prelude (Little One) & Baby

Producer: James William Guercio

Length (mins): 00:44:39

Label: Columbia

Genres (Music): Rock music

11
Chicago 16 is listed (or ranked) 11 on the list The Best Chicago Albums of All Time
By Chicago (1982); Tracks: Rescue You, Waiting for You to Decide & Follow Me

Producer: David Foster

Length (mins): 00:41:53

Genres (Music): Rock music, Adult contemporary music

12
Hot Streets is listed (or ranked) 12 on the list The Best Chicago Albums of All Time
By Chicago (1978); Tracks: Ain't It Time, The Greatest Love on Earth & Love Was New

Producer: Phil Ramone

Length (mins): 00:41:48

Genres (Music): Rock music, Rock and roll, Jazz fusion

13
Chicago 18 is listed (or ranked) 13 on the list The Best Chicago Albums of All Time
By Chicago (1986); Tracks: Will You Still Love Me?, One More Day & 25 or 6 to 4

Producer: David Foster

Genres (Music): Rock music, Adult contemporary music

14
Chicago 19 is listed (or ranked) 14 on the list The Best Chicago Albums of All Time
By Chicago (1988); Tracks: What Kind of Man Would I Be?, You're Not Alone & Look Away

Length (mins): 00:44:26

Genres (Music): Rock music, Adult contemporary music

15
Chicago XXXII: Stone of ... is listed (or ranked) 15 on the list The Best Chicago Albums of All Time
By Chicago (2008); Tracks: Stone of Sisyphus (No Rhythm Loop), All the Years & Sleeping in the Middle of the Bed

Genres (Music): Rock music, Adult contemporary music

16
Chicago 13 is listed (or ranked) 16 on the list The Best Chicago Albums of All Time
By Chicago (1979); Tracks: Run Away, Window Dreamin' & Mama Take

Producer: Phil Ramone

Length (mins): 00:47:10

Label: Columbia

Genres (Music): Rock music, Rock and roll, Disco

17
Now Chicago XXXVI is listed (or ranked) 17 on the list The Best Chicago Albums of All Time
18
Night and Day: Big-Band ... is listed (or ranked) 18 on the list The Best Chicago Albums of All Time
By Chicago (1995); Tracks: Take the "A" Train, Sophisticated Lady & Goody Goody

Producer: Bruce Fairbairn

Length (mins): 00:51:29

Genres (Music): Big Band

19
Chicago XIV is listed (or ranked) 19 on the list The Best Chicago Albums of All Time
By Chicago (1980); Tracks: Birthday Boy, Hold On & Overnight Cafe

Producer: Thomas J. Dowd

Length (mins): 00:38:35

Genres (Music): Rock music, Rock and roll

20
Twenty 1 is listed (or ranked) 20 on the list The Best Chicago Albums of All Time
By Chicago (1991); Tracks: You Come to my Senses, What Does It Take & Only Time Can Heal the Wounded

Producer: Humberto Gatica

Length (mins): 00:52:03

Genres (Music): Rock music, Adult contemporary music

21
Chicago XXX is listed (or ranked) 21 on the list The Best Chicago Albums of All Time
By Chicago (2006); Tracks: Already Gone, Where Were You & 90 Degrees and Freezing

Genres (Music): Rock music, Adult contemporary music, Rock and roll

22
Live is listed (or ranked) 22 on the list The Best Chicago Albums of All Time
23
Chicago 25: the Christma... is listed (or ranked) 23 on the list The Best Chicago Albums of All Time
24
The Nashville Sessions ... is listed (or ranked) 24 on the list The Best Chicago Albums of All Time
By Leftover Salmon (1999); Tracks: Midnight Blues, Nobody's Fault But Mine & On the Other Side

Length (mins): 00:58:45

25
O Christmas Three is listed (or ranked) 25 on the list The Best Chicago Albums of All Time
By Chicago (2011); Tracks: What Are You Doing New Years Eve?, O Christmas Tree & I Saw Three Ships

Genres (Music): Rock music, Adult contemporary music, Christmas music