Chicago: A Retrospective (1967-2007)

Chicago A Retrospective: 1967-2007

Overview: Chicago formed in 1967. They were originally known as The Big Thing and later the Chicago Transit Authority. Thanks to Lee Loughnane, James Pankow (both still with the band today), and Walt Parazaider, the band brought a jazzy quality to rock and roll with their horn section. It defined their sound through the late ‘60s and ‘70s. However, after getting dropped by their label, they shifted to a more adult contemporary sound in the ‘80s and had a commercial resurgence. The Players This is not a complete list. The focus is just on those members who were part of the band from 1967 through 2009. Dawayne Bailey (guitar/vocals: 1986-95) Peter Cetera (vocals/bass: 1967-85) * Bill Champlin (keyboards/vocals: 1981-2009) Donnie Dacus (guitar/vocals: 1978-80) Laudir de Oliveira (percussion: 1973-81) Bruce Gaitsch (guitar: 1995) Keith Howland (guitar/backing vocals: 1995-2021) Tris Imboden (drums/harmonica: 1990-2018) Terry Kath (guitar: 1967-78) * Robert Lamm (keyboard/vocals: 1967-) * Lee Loughnane (trumpet: 1967-) * James Pankow (trombone: 1967-) * Walt Parazaider (reeds: 1967-2017) * Chris Pinnick (guitar: 1980-85) Jason Scheff (vocals: 1985-2016) Danny Seraphine (drums: 1967-90) * * inducted into the Rock and Roll Hall of Fame in 2016 as members of Chicago Links DMDB encyclopedia entry for Chicago ChicagoTheBand.com (official site) Wikipedia

Awards:

Compilations This page highlights all of the songs featured on these compilations. IX Chicago IX: Greatest Hits (1969-73, released 1975) II Greatest Hits Volume II (1969-78, released 1981) 82 Greatest Hits 1982-1989 (1982-89, released 1989) VB The Very Best of: Only the Beginning (1969-95, released 2002) H1 The Heart of Chicago 1967-1997 (1967-97, released 1997) H2 The Heart of Chicago, Volume II (1969-98, released 1998) 40 The Best of Chicago: 40th Anniversary (1969-2005, released 2007) Songs featured on any of the above anthologies are noted below chronologically under the studio albums under which they originally appeared. If the song charted, the date of the song’s release or first chart appearance and its peaks on various charts are noted in parentheses. Click for codes to charts. Spotify Playlist Check out my Spotify playlist Chicago 1969-1995 to get nearly all of the songs mentioned on this page in one big 42-song playlist.

1969-1975 Chicago released seven studio albums in this time period, generating 16 top-40 singles – 11 of which reached the top 10. Here are the tracks from those albums that are featured on the noted compilations. Chicago Transit Authority (1969) Questions 67 & 68 (8/9/69, 24 BB, 13 CB, 15 GR, 17 HR, 34 AC, 12 CL, 54 CN, 11 DF) II,VB I’m a Man (1/10/70, 49 BB, 67 CB, 17 HR, 9 CL, 8 UK, 8 CN, 10 DF) H2,VB,40 Does Anybody Really Know What Time It Is? (11/6/70, 7 BB, 5 CB, 7 GR, 6 HR, 5 AC, 5 CL, 2 CN, 35 AU, 5 DF) IX,H1,VB,40 Beginnings (6/25/71, 7 BB, 11 CB, 6 GR, 7 HR, 1 AC, 7 CL, 8 CN, 6 DF) IX,H1,BB,40 Chicago II (1970) Make Me Smile (3/28/70, 9 BB, 11 CB, 11 GR, 13 HR, 9 CL, 11 CN, 33 AU, 22 DF) IXH1,VB,40 25 or 6 to 4 (6/18/70, 4 BB, 6 CB, 5 GR, 6 HR, 3 CL, 7 UK, 2 CN, 12 AU, 1 DF) IX,H2,VB,40 Colour My World (6/26/71, 7 BB, 75 CB, 7 HR, 6 CL, 21 DF) IX,H1,VB,40 Chicago III (1971) Free (2/19/71, 20 BB, 19 CB, 27 GR, 27 HR, 27 CL, 12 CN, 99 AU, 36 DF) VB Lowdown (5/8/71, 35 BB, 25 CB, 35 GR, 25 HR, 29 CL, 19 CN) VB Chicago V (1972) Saturday in the Park (7/29/72, 3 BB, 3 CB, 2 GR, 3 HR, 8 AC, 3 CL, 2 CN, 43 AU, 1 DF) IX,H1,VB,40 Dialogue (Part I & II) (10/21/72, 24 BB, 17 CB, 24 GR, 25 HR, 26 CL, 26 CN, 91 AU, 11 DF) II,H2,VB Chicago VI (1973) Feelin’ Stronger Everyday (6/22/73, 10 BB, 8 CB, 6 GR, 11 HR, 8 CL, 12 CN, 74 AU, 16 DF) IX,H2,VB,40 Just You ‘N’ Me (9/28/73, 4 BB, 1 CB, 3 GR, 2 HR, 4 RR, 7 AC, 1 CL, 3 CN, 23 AU, 21 DF) IX,H1,VB,40 Chicago VII (1974) I’ve Been Searching So Long (3/16/74, 9 BB, 7 CB, 3 GR, 5 HR, 6 RR, 8 AC, 21 CL, 5 CN, 44 AU, 16 DF) IX,H2,VB,40 Call on Me (6/22/74, 6 BB, 10 CB, 16 GR, 11 HR, 17 RR, 1 AC, 21 CL, 9 CN, 27 DF) VB,40 Wishing You Were Here (10/12/74, 11 BB, 9 CB, 9 GR, 12 HR, 12 RR, 1 AC, 17 CL, 51 UK, 12 CN, 51 AU, 14 DF) IX,H1,VB,40 Happy ManII,VB Chicago VIII (1975) Old Days (4/25/75, 5 BB, 6 CB, 11 GR, 8 HR, 7 RR, 3 AC, 18 CL, 6 CN, 80 AU, 22 DF) II,H2,VB,40

Chicago IX: Greatest Hits Chicago

Recorded: 1969-1975 Released: November 10, 1975 Peak: 15 US, -- UK, 12 CN, 16 AU, 12 DF Sales (in millions): 5.0 US Genre: jazz rock/classic rock Rating: 4.380 out of 5.00 (average of 9 ratings)

Awards: (Click on award to learn more).

Tracks: (1) 25 or 6 to 4 (2) Does Anybody Really Know What Time It Is? (3) Colour My World (4) Just You ‘N’ Me (5) Saturday in the Park (6) Feelin’ Stronger Every Day (7) Make Me Smile (8) Wishing You Were Here (9) Call on Me (10) I’ve Been Searching So Long (11) Beginnings About the Album: In just six years, Chicago had released seven studio albums and a live album. For their ninth outing, they released this chart-topping compilation that gathered up 11 of their hits from the era.

1976-1981 Chicago released five studio albums during this period, but their commercial clout was beginning to slip. Chicago 13 (1979) became the band’s first album to miss platinum status and then Chicago XIV (1980) didn’t even go gold. Chicago X (1976) Another Rainy Day in New York City (6/25/76, 32 BB, 33 CB, 26 GR, 31 H, 36 RR, 2 AC, 25 CL, 37 CN) VB,40 If You Leave Me Now (7/30/76, 1 BB, 1 CB, 1 GR, 1 HR, 1 RR, 1 AC, 1 CL, 1 UK, 1 CN, 1 AU, 1 DF) II,H1,VB,40 Chicago XI (1977) Baby What a Big Surprise (9/23/77, 4 BB, 4 CB, 3 GR, 8 HR, 3 RR, 8 AC, 2 CL, 41 UK, 3 CN, 14 AU, 15 DF) II,H2,VB,40 Take Me Back to Chicago (5/13/78, 63 BB, 62 CB, 55 HR, 39 AC, 33 CL, 66 CN, 27 DF) II,VB Hot Streets (1978) Alive Again (10/13/78, 14 BB, 13 CB, 9 GR, 12 HR, 7 RR, 39 AC, 22 CL, 11 CN, 37 AU, 33 DF) II,VB No Tell Lover (12/23/78, 14 BB, 14 CB, 11 GR, 18 HR, 9 RR, 5 AC, 22 CL, 10 CN, 67 AU, 33 DF) II,H2,VB,40 Gone Long Gone (4/14/79, 73 BB, 75 CB, 97 HR, 42 CL, 93 CN) II

Greatest Hits Volume II Chicago

Recorded: 1969-1978 Released: November 23, 1981 Peak: 171 US, -- UK, -- CN, -- AU Sales (in millions): -- Genre: jazz rock/classic rock Rating: 3.569 out of 5.00 (average of 8 ratings)

Tracks: (1) About the Album: After the poor reception of 1980’s Chicago XIV, the band’s label, Columbia Records, dropped them. They capped the era with another greatest hits collection. The band only had two top-ten hits from this era so there wasn’t much to celebrate and the compilation fell flat. It didn’t even pull anything from the band’s most recent two albums, given their relative failure.

1982-1989 These could be called the “David Foster” years. Other than Chicago 19, Foster served as the producer and – for better or worse – reinvented the band as an adult-contemporary juggernaut. It did bring them back to commercial relevance with the #1 hits “Hard to Say I’m Sorry” and “Look Away” and two multi-platinum albums. The band did fall back a little after lead singer Peter Cetera left in 1985 for a solo career, but then roared back with an all-new band achievement – four top-10 hits from their Chicago 19 album. Chicago 16 (1982) Hardy to Say I’m Sorry (5/17/82, 1 BB, 1 CB, 1 GR, 1 RR, 1 AC, 4 UK, 1 CN, 4 AU, 4 DF) 82,H1,VB,40 Love Me Tomorrow (9/25/82, 22 BB, 22 CB, 2 GR, 4 RR, 8 AC, 35 CN, 82 AU, 21 DF) 82,H2,VB,40 Get Away (27 DF) 82,V1,VB Chicago 17 (1984) Stay the Night (5/4/84, 16 BB, 15 CB, 13 GR, 11 RR, 7 AR, 47 CN, 1 DF) 82,H2,VB Hard Habit to Break (8/3/84,3 BB, 2 CB, 1 G, 1 RR, 3 AC, 8 UK, 5 CN, 20 AU, 2 DF) 82,H1,VB,40 You’re the Inspiration (11/16/84, 3 BB, 1 BA, 4 CB, 2 GR, 1 RR, 1 AC, 14 UK, 5 CN, 43 AU, 3 DF) 82,H2,VB Along Comes a Woman (2/22/85, 14 BB, 19 CB, 5 GR, 7 RR, 25 AC, 10 AR, 96 UK, 17 CN, 5 DF) 82,VB Chicago 18 (1986) Will You Still Love Me? (11/15/86, 3 BB, 4 CB, 2 GR, 2 RR, 2 AC, 6 CN, 24 DF) 82,H1,VB,40 If She Would Have Been Faithful (3/21/87, 17 BB, 16 CB, 10 GR, 12 RR, 9 AC, 54 CN, 14 DF) 82,VB,40 Chicago 19 (1988) I Don’t Wanna Live Without Your Love (6/4/88, 3 B, 5 CB, 2 GR, 3 RR, 5 AC, 4 CN, 60 AU, 22 DF) 82,H2,VB Look Away (9/23/88, 1 BB, 1 BA, 1 CB, 1 GR, 1 RR, 1 AC, 77 UK, 1 CN, 12 DF) 82,H1,VB,40 You’re Not Alone (1/21/89, 10 BB, 9 CB, 7 GR, 9 RR, 9 AC, 22 CN, 27 DF) H2,VB,40 We Can Last Forever (5/6/89, 55 BB, 53 CB, 12 AC, 74 CN, 26 DF) 82,VB What Kind of Man Would I Be? (12/2/89, 5 BB, 5 CB, 2 GR, 4 RR, 2 AC, 4 CN, 27 DF) 82,H2,VB,40

Greatest Hits 1982-1989 Chicago

Recorded: 1982-1989 Released: November 21, 1989 Peak: 37 US, 6 UK, 73 CN, 71 AU Sales (in millions): 5.0 Genre: jazz rock/classic rock Rating: 4.413 out of 5.00 (average of 8 ratings)

Tracks: (1) Hard to Say I’m Sorry/Get Away (2) Look Away (3) Stay the Night (4) Will You Still Love Me? (5) Love Me Tomorrow (6) What Kind of Man Would I Be? (7) You’re the Inspiration (8) I Don’t Wanna Live Without Your Love (9) Hard Habit to Break (10) Along Comes a Woman (11) If She Would Have Been Faithful (12) We Can Last Forever About the Album: Producer David Foster had stripped away the jazz-meets-rock sound that made Chicago so beloved and replaced it with middle-of-the-road balladry. To be fair, they were well-constructed songs that were embraced by adult contemporary and top-40 radio, giving Chicago a career renaissance. It just wasn’t the same band. Like the previous two compilations, this one didn’t have anything new, although “What Kind of Man Would I Be?,” a song from Chicago 19, was released as a single to support this collection.

The Very Best of: Only the Beginning Chicago

Recorded: 1969-1995 Released: July 2, 2002 Peak: 20 US, 11 UK, -- CN, 86 AU Sales (in millions): 2.0 US, 0.1 UK Genre: jazz rock/classic rock Rating: 3.951 out of 5.00 (average of 7 ratings)

Awards: (Click on award to learn more).

Tracks, Disc 1: (1) Make Me Smile (2) 25 or 6 to 4 (3) Does Anybody Really Know What Time It Is? (4) Beginnings (5) Questions 67 & 68 (6) I’m a Man (7) Colour My World (8) Free (9) Lowdown (10) Saturday in the Park (11) Dialogue (Part I & II) (12) Just You ‘N’ Me (13) Feelin’ Stronger Every Day (14) I’ve Been Searching So Long (15) Wishing You Were Here (16) Call on Me (17) Happy Man (18) Another Rainy Day in New York City (19) If You Leave Me Now Tracks, Disc 2: (1) Old Days (2) Baby What a Big Surprise (3) Take Me Back to Chicago (4) Alive Again (5) No Tell Lover (6) Love Me Tomorrow (7) Hard to Say I’m Sorry/Get Away (8) Stay the Night (9) Hard Habit to Break (10) You’re the Inspiration (11) Along Comes a Woman (12) Will You Still Love Me? (13) If She Would Have Been Faithful (14) Look Away (15) What Kind of Man Would I Be? (16) I Don’t Wanna Live Without Your Love (17) We Can Last Forever (18) You’re Not Alone (19) Chasin’ the Wind (20) Sing, Sing, Sing Tracks Not on Previously Noted Albums: Chasin’ the Wind ((from 1991 album Twenty One, 1/19/91, 39 BB, 31 CB, 24 GR, 37 RR, 13 AC, 50 CN, 38 DF) VB Sing Sing Sing (from 1995 album Night & Day) VB About the Album: This is a vastly superior collection to the Heart of Chicago compilations released in 1997 and ’98. First, this set puts the songs in chronological order – although it weirdly starts off with a couple songs from the second album and then moves to material from the first album. Chicago is also a band that has amassed so many hits at this point in their career that a single-disc retrospective is bound to fail. Thankfully this collection works – although it could have stopped in 1989 and jettisoned the two forgettable songs from the ‘90s.

The Heart of Chicago 1967-1997 Chicago

Recorded: 1967-1997 Released: April 22, 1997 Peak: 55 US, 21 UK, 47 CN, -- AU Sales (in millions): 0.5 Genre: jazz rock/classic rock Rating: 4.060 out of 5.00 (average of 13 ratings)

Tracks: (1) You’re the Inspiration (2) If You Leave Me Now (3) Make Me Smile (4) Hard Habit to Break (5) Saturday in the Park (6) Wishing You Were Here (7) The Only One (8) Colour My World (9) Look Away (10) Here in My Heart (11) Just You ‘N’ Me (12) Does Anybody Really Know What Time It Is? (13) Will You Still Love Me? (14) Beginnings (15) Hard to Say I’m Sorry/Get Away Tracks Not on Previously Noted Albums: Here in My Heart (4/19/97, 59 BB, 1 AC) H1,40 The Only One (10/11/97, 17 AC) H1 About the Album: This is why I’m not a fan of non-chronological compilations. Jumping back and forth between the jazz-rock of Chicago’s early days on such songs as “Beginnings” and “Does Anybody Really Know What Time It Is?” and the David Foster-produced adult contemporary ballad of latter years like “You’re the Inspiration” and “Look Away” makes for a very disjointed listening experience. A listener is much better served by plopping down the cash for the first three compilations highlighted here.

The Heart of Chicago Volume II Chicago

Recorded: 1969-1998 Released: May 12, 1998 Peak: 154 US, -- UK, -- CN, -- AU Sales (in millions): 0.5 Genre: jazz rock/classic rock Rating: 3.559 out of 5.00 (average of 13 ratings)

Tracks: (1) Dialogue (Part I & II) (2) Old Days (3) All Roads Lead to You (4) Love Me Tomorrow (5) Baby What a Big Surprise (6) You’re Not Alone (7) What Kind of Man Would I Be? (8) No Tell Lover (9) Show me a Sign (10) I’ve Been Searching So Long (11) Call on Me (12) I Don’t Wanna Live Without Your Love (13) Feelin’ Stronger Every Day (14) Stay the Night (15) I’m a Man (16) 25 or 6 to 4 Tracks Not on Previously Noted Albums: All Roads Lead to You (6/6/98, 14 AC) H2 Show Me a Sign (4/17/99, 28 AC) H2 About the Album: This collection is even less necessary than its predecessor. Once again, the mix of old and new Chicago creates a sort of Jekyll and Hyde experience where the listener never knows which version of the band they’ll get from one song to the next. That’s bad enough, but then this collection is comprised of the songs that weren’t considered worthy for the first set. To be fair, Chicago has more than enough great songs to flesh out multiple compilations but the way these two packages were put together leaves one feeling like they already got the cream of the crop via the first set. The one glaring exception – “25 or 6 to 4.” How did that not make the first collection?

The Best of Chicago: 40th Anniversary Edition Chicago

Recorded: 1969-2005 Released: October 2, 2007 Peak: 100 US, -- UK, -- CN, -- AU Sales (in millions): 0.5 US Genre: jazz rock/classic rock Rating: 3.939 out of 5.00 (average of 11 ratings)

Tracks, Disc 1: (1) Questions 67 & 68 (2) 25 or 6 to 4 (3) Does Anybody Really Know What Time It Is? (4) Make Me Smile (5) Beginnings (6) Colour My World (7) Saturday in the Park (8) Feelin’ Stronger Every Day (9) Just You ‘N’ Me (10) I’ve Been Searching So Long (11) Call on Me (12) Wishing You Were Here (13) Old Days (14) Another Rainy Day in New York City (15) If You Leave Me Now Tracks, Disc 2: (1) Baby What a Big Surprise (2) No Tell Lover (3) Hard to Say I’m Sorry (4) Love Me Tomorrow (5) Hard Habit to Break (6) You’re the Inspiration (7) Will You Still Love Me? (8) If She Would Have Been Faithful (9) I Don’t Wanna Live Without Your Love (10) Look Away (11) What Kind of Man Would I Be? (12) You’re Not Alone (13) Here in My Heart (14) Feel (15) Love Will Come Back Tracks Not on Previously Noted Albums: Feel (from 2006 album XXX, 3/25/06, 19 AC) 40 Love Will Come Back (from 2006 album XXX, 5/13/06, 21 AC) 40 About the Album: This collection isn’t vastly different from The Very Best of: Only the Beginning, which was released just five years prior. Both collections benefit from presenting the songs chronologically and being two-disc packages. This set, however, isn’t as impressive considering they trimmed the number of songs down from 39 on the earlier set to just 30 here.

Resources and Related Links: DMDB encyclopedia entry for Chicago Dave’s Music Database: Acts’ Profile Pages and Best-of Lists First posted 7/17/2025.