# Chicago discography

Chicago is an American rock band formed in 1967 in Chicago, Illinois. The self-described "rock and roll band with horns" began as a politically charged, sometimes experimental, rock band and later moved to a predominantly softer sound, generating several hit ballads. The group had a steady stream of hits throughout the 1970s and 1980s. Second only to The Beach Boys in Billboard singles and albums chart success among American bands, Chicago is one of the longest-running and most successful rock groups, and one of the world's best-selling groups of all time, having sold more than 100 million records.
According to Billboard, Chicago was the leading US singles charting group during the 1970s. They have sold over 40 million units in the US, with 23 gold, 18 platinum, and 8 multi-platinum albums. Over the course of their career they have had five number-one albums and 21 top-ten singles. They were inducted into the Rock and Roll Hall of Fame on April 8, 2016 at Barclays Center in Brooklyn, New York.

## Albums
### Canon albums

List of albums, with selected chart positions, sales figures and certifications :
| No. | Title | Album details | Peak chart positions | Peak chart positions | Peak chart positions | Peak chart positions | Peak chart positions | Peak chart positions | Peak chart positions | Peak chart positions | Peak chart positions | Peak chart positions | Peak chart positions | Peak chart positions | Certifications |
| No. | Title | Album details | US | AUS | CAN | FIN | FR | GER | ITA | NDL | NO | NZ | SWE | UK | Certifications |
| 1 | The Chicago Transit Authority | Released: April 28, 1969 Label: Columbia Formats: LP, cassette, CD, 8-track Cover design: Painted shingle | 17 | 23 | 10 | — | 1 | — | — | 6 | 8 | — | — | 9 | US: 2× Platinum CAN: Platinum |
| 2 | Chicago | Released: January 26, 1970 Label: Columbia Formats: LP, cassette, CD, 8-track Cover design: Silver bar | 4 | 5 | 4 | — | 13 | 20 | 8 | 2 | — | — | 7 | 6 | US: Platinum CAN: 3× Platinum |
| 3 | Chicago III | Released: January 11, 1971 Label: Columbia Formats: LP, cassette, 8-track Cover design: Tattered flag | 2 | 6 | 7 | 6 | — | 17 | 9 | 5 | 8 | — | 5 | 9 | US: Platinum CAN: Gold |
| 4 | Chicago at Carnegie Hall | Released: October 25, 1971 Label: Columbia Formats: LP, cassette, CD, 8-track Cover design: White tile | 3 | 26 | 3 | — | — | — | — | — | — | — | — | — | US: Platinum CAN: Gold |
| 5 | Chicago V | Released: July 10, 1972 Label: Columbia Formats: LP, cassette, CD, 8-track Cover design: Carved wood | 1 | 5 | 1 | 14 | — | — | 13 | 4 | 7 | — | 5 | 24 | US: 2× Platinum CAN: Platinum |
| 6 | Chicago VI | Released: June 25, 1973 Label: Columbia Formats: LP, cassette, CD, 8-track Cover design: Engraved bill | 1 | 12 | 2 | 26 | — | — | 22 | — | 13 | — | 3 | — | US: 2× Platinum CAN: Platinum |
| 7 | Chicago VII | Released: March 11, 1974 Label: Columbia Formats: LP, cassette, CD, 8-track Cover design: Embossed leather | 1 | 13 | 4 | — | — | — | — | — | 13 | — | 18 | — | US: Platinum CAN: Gold |
| 8 | Chicago VIII | Released: March 24, 1975 Label: Columbia Formats: LP, cassette, CD, 8-track Cover design: Embroidered textile | 1 | 27 | 3 | — | 17 | — | — | — | 6 | 30 | 25 | — | US: Platinum CAN: Gold |
| 9 | Chicago IX: Chicago's Greatest Hits | Released: November 10, 1975 Label: Columbia Formats: LP, cassette, CD, 8-track Cover design: Painted billboard | 1 | 16 | 1 | — | — | — | — | — | — | 7 | — | — | US: 5× Platinum CAN: 3× Platinum |
| 10 | Chicago X | Released: June 14, 1976 Label: Columbia Formats: LP, cassette, CD, 8-track Cover design: Chocolate bar | 3 | 3 | 3 | — | — | 5 | 8 | 4 | 7 | 6 | 6 | 21 | US: 2× Platinum CAN: Platinum UK: Silver |
| 11 | Chicago XI | Released: September 12, 1977 Label: Columbia Formats: LP, cassette, CD, 8-track Cover design: Regional map | 6 | 7 | 4 | — | 8 | 39 | 15 | 12 | 5 | — | 8 | — | US: Platinum CAN: Platinum |
| 12 | Hot Streets | Released: October 2, 1978 Label: Columbia Formats: LP, cassette, CD, 8-track Cover design: Photo of band | 12 | 14 | 10 | — | 25 | — | — | — | 7 | 9 | 23 | — | US: Platinum CAN: Platinum |
| 13 | Chicago 13 | Released: August 13, 1979 Label: Columbia Formats: LP, cassette, CD, 8-track Cover design: Marina City tower | 21 | 24 | 21 | — | — | — | — | — | 16 | — | 30 | — | US: Gold CAN: Gold |
| 14 | Chicago XIV | Released: July 21, 1980 Label: Columbia Formats: LP, cassette, CD, 8-track Cover design: Fingerprint | 71 | 71 | 60 | — | — | — | — | — | — | — | 46 | — | |
| 15 | Greatest Hits, Volume II | Released: November 23, 1981 Label: Columbia Formats: LP, cassette, CD, 8-track Cover design: Series of signs | 171 | — | — | — | — | — | — | — | — | — | — | — | |
| 16 | Chicago 16 | Released: June 7, 1982 Label: Full Moon Formats: LP, cassette, CD, 8-track Cover design: Computer chip | 9 | 22 | 17 | — | — | 11 | 13 | 33 | — | 24 | — | 44 | US: Platinum CAN: Gold |
| 17 | Chicago 17 | Released: May 14, 1984 Label: Full Moon Formats: LP, cassette, CD, 8-track Cover design: Brown paper package | 4 | 65 | 4 | — | 23 | 12 | — | 20 | 14 | 25 | 1 | 24 | US: 6× Platinum UK: Gold |
| 18 | Chicago 18 | Released: September 29, 1986 Label: Full Moon Formats: LP, cassette, CD, 8-track Cover design: Mosaic tiles | 35 | — | 53 | 31 | — | 49 | — | — | 12 | — | 15 | — | US: Gold |
| 19 | Chicago 19 | Released: June 20, 1988 Label: Full Moon Formats: LP, cassette, CD, 8-track Cover design: Modern painting | 37 | — | 38 | 39 | — | 42 | — | — | 5 | — | 7 | — | US: Platinum |
| 20 | Greatest Hits 1982–1989 Issued as: The Heart of Chicago in Europe. | Released: November 21, 1989 Label: Full Moon Formats: LP, cassette, CD Cover design: Masonry | 37 | 71 | 73 | — | — | 47 | 23 | — | — | — | — | 6 | US: 5× Platinum AUS: Gold CAN: Gold UK: Platinum |
| 21 | Twenty 1 | Released: January 29, 1991 Label: Full Moon Formats: LP, cassette, CD Cover design: Painted number "1" | 66 | — | 73 | 40 | — | 66 | — | 52 | 11 | — | 18 | — | |
| 22 | Night & Day: Big Band | Released: May 23, 1995 Label: Giant Formats: cassette, CD Cover design: Musical instruments | 90 | — | — | — | — | — | — | — | — | — | — | — | |
| 23 | The Heart of Chicago 1967–1997 | Released: April 22, 1997 Label: Reprise Formats: cassette, CD Cover design: Red satin | 55 | — | 47 | 8 | — | — | — | 2 | 4 | 41 | — | 21 | US: Gold AUS: Gold |
| 24 | The Heart of Chicago 1967–1998 Volume II | Released: May 12, 1998 Label: Reprise Formats: cassette, CD Cover design: Blue satin | 154 | — | — | — | — | — | — | — | — | — | — | — | |
| 25 | Chicago XXV: The Christmas Album Reissued as: What's It Gonna Be, Santa? (2003). | Released: August 25, 1998 Label: Chicago Formats: cassette, CD Cover design: Christmas wreath | 47 | — | — | — | — | — | — | — | — | — | — | — | US: Gold |
| 26 | Chicago XXVI: Live in Concert | Released: October 12, 1999 Label: Chicago Formats: CD Cover design: Billboard on highway | — | — | — | — | — | — | — | — | — | — | — | — | |
| 27 | The Very Best of Chicago: Only the Beginning Issued as: The Chicago Story: Complete Greatest Hits in Europe. | Released: July 2, 2002 Label: Rhino Formats: CD Cover design: Green grass logo | 20 | 86 | — | — | — | 25 | — | 4 | — | — | — | 11 | US: 2× Platinum AUS: Gold UK: Gold |
| 28 | The Box | Released: July 22, 2003 Label: Rhino Formats: CD Cover design: Pushed out pins | — | — | — | — | — | — | — | — | — | — | — | — | |
| 29 | Love Songs | Released: January 25, 2005 Label: Rhino Formats: CD, download Cover design: Rose petals with box of chocolates & stemmed roses | 57 | — | — | — | — | — | — | — | — | — | 5 | — | |
| 30 | Chicago XXX | Released: March 21, 2006 Label: Rhino Formats: CD, download Cover design: Granite inlay on concrete with jackhammered XXX cutouts | 41 | — | — | — | — | — | — | — | — | — | — | — | |
| 31 | The Best of Chicago: 40th Anniversary Edition | Released: October 2, 2007 Label: Rhino Formats: CD, download Cover design: Red wax seal | 100 | — | — | — | — | — | — | — | — | — | — | — | US: Gold |
| 32 | Chicago XXXII: Stone of Sisyphus | Released: June 17, 2008 Label: Rhino Formats: CD, download Cover design: Chiseled out of stone boulder | 122 | — | — | — | — | — | — | — | — | — | — | — | |
| 33 | Chicago XXXIII: O Christmas Three | Released: October 4, 2011 Label: Chicago Records II Formats: CD, download Cover design: Candy cane | 170 | — | — | — | — | — | — | — | — | — | — | — | |
| 34 | Chicago XXXIV: Live in '75 | Released: May 24, 2011 Label: Rhino Formats: CD, download Cover design: Sun and clouds special logo | — | — | — | — | — | — | — | — | — | — | — | — | |
| 35 | Chicago XXXV: The Nashville Sessions | Released: April 26, 2013 Label: Chicago Records II Formats: CD, download Cover design: Map with Nashville at top | — | — | — | — | — | — | — | — | — | — | — | — | |
| 36 | Chicago XXXVI: Now | Released: July 4, 2014 Label: Frontiers Formats: CD, download Cover design: Swirling black-and-white checkerboard | 82 | — | — | — | — | 56 | — | — | — | — | — | 181 | |
| 37 | Chicago XXXVII: Chicago Christmas | Released: October 11, 2019 Label: Rhino Formats: LP, CD, download Cover design: Green-and-white striped wrapped gift with red bow | — | — | — | — | — | — | — | — | — | — | — | — | |
| 38 | Chicago XXXVIII: Born for This Moment | Released: July 15, 2022 Label: BMG Formats: LP, CD, download Cover design: Brushed gold | — | — | — | — | — | — | — | — | — | — | — | — | |
| 39 | Chicago Greatest Christmas Hits | Released: November 3, 2023 Label: Rhino Formats: LP, CD, download Cover design: Ornaments and garland on tree | — | — | — | — | — | — | — | — | — | — | — | — | |
| 40 | Chicago At The John F. Kennedy Center For The Performing Arts, Washington D.C. (9/16/71) | Released: September 27, 2024 Label: Rhino Formats: LP, CD, download Cover design: Psychedelic pattern | — | — | — | — | — | — | — | — | — | — | — | — | |
Notes:

### Other albums

Live albums
* 1972: Live in Japan
* 2015: Chicago at Symphony Hall
* 2018: Chicago: VI Decades Live (This is What We Do) (box set)
* 2018: Chicago: Chicago II Live on Soundstage
* 2018: Chicago: Greatest Hits Live
* 2018: Chicago: Live at the Isle of Wight Festival
Compilation albums
* 1983: If You Leave Me Now
* 1984: The Ultimate Collection
* 1985: Take Me Back to Chicago
* 1991: Group Portrait
* 1995: Overtime
* 1995: 25 Years of Gold – AUS #30
* 1996: The Very Best of Chicago
* 1997: Chicago Presents the Innovative Guitar of Terry Kath
* 2013: Chicago Collectors Edition (3 CD set from Madacy Records)

## Unauthorized releases

In 1969, Chicago appeared at the Toronto Rock and Roll Revival, the same one day rock festival that produced John Lennon's Live Peace in Toronto 1969. (Also appearing at the Festival were Alice Cooper, Bo Diddley and Chuck Berry - whose performances of the event were also issued on albums.) Since 1978, there have been innumerable unauthorized LP, Cassette and CD releases of the same poor-quality recording of this performance.
There were eight songs recorded at the gig, seven from Chicago Transit Authority plus the then unreleased "25 or 6 to 4." Almost all of these releases include only seven of the songs; "Beginnings" is nearly always omitted, its title often being wrongly given to the first track "Introduction". "South California Purples" is often listed as "Purples," "Purple Song" or "South Carolina Purples", and sometimes given an incorrect writing credit—i.e., to composer Carl Michalski or "John Gunner/J.Marks".
The one song in the set not to appear previously on any official live album is "Liberation", which is frequently edited or faded early and whose correct total runtime is approximately 16:05. On some versions, all the songs are faded early. Some LP versions include talking between songs, most notably Lamm pointing out that "25 or 6 to 4" was a brand new song.
Despite its shortcomings, some reviewers have regarded the recording quite positively. For example, the 1984 LP release Chicago: Toronto Rock 'n' Roll Revival 69 by Design Records is considered by reviewer Doug Stone to be a "choice concert souvenir...captur(ing) the group in its live prime. Supporting the Chicago Transit Authority debut, before mastering wedding material, Chicago was a rock & roll force to be reckoned with." A reviewer of an earlier version of the same recording, entitled Toronto Rock 'n' Roll Revival 1969, Volume 1 (Accord, 1981) considers that "...there's certainly nothing wrong with the performance. In some ways, the at times fuzzy sound works in the album's favor, giving Chicago a garage-y edge rarely found on their studio works."

## Singles

| Year | Title | US | US AC | AUS | UK | IRE | CAN | US CB | Certification | Lead singer | Album | B-side | Label and cat# |
| July 1969 | "Questions 67 and 68" | 71 | — | — | — | — | 54 | 82 | | Peter Cetera/Robert Lamm | Chicago Transit Authority | "Listen" | Columbia 44909 |
| Oct. 1969 | "Beginnings" | — | — | — | — | — | — | — | | Lamm | Chicago Transit Authority | "Poem 58" | Columbia 45011 |
| March 1970 | "Make Me Smile" | 9 | — | 33 | — | — | 11 | 11 | | Terry Kath | Chicago | "Colour My World" | Columbia 45127 |
| June 1970 | "25 or 6 to 4" | 4 | — | 12 | 7 | 13 | 2 | 6 | | Cetera | Chicago | "Where Do We Go from Here" | Columbia 45194 |
| Oct. 1970 | "Does Anybody Really Know What Time It Is?" | 7 | 5 | 35 | — | — | 2 | 5 | | Lamm | Chicago Transit Authority | "Listen" | Columbia 45264 |
| Feb. 1971 | "Free" | 20 | — | 99 | — | — | 12 | 19 | | Kath | Chicago III | "Free Country" | Columbia 45331 |
| April 1971 | "Lowdown" | 35 | — | — | — | — | 19 | 25 | | Cetera | Chicago III | "Loneliness Is Just a Word" | Columbia 45370 |
| June 1971 | "Beginnings" (A-side) | 7 | 1 | — | — | — | 8 | 11 | | Lamm | Chicago Transit Authority | | Columbia 45417 |
| June 1971 | → "Colour My World" (B-side) | 7 | — | — | — | — | — | 75 | | Kath | Chicago | | Columbia 45417 |
| Sept. 1971 | "Questions 67 and 68" (A-side) | 24 | 34 | — | — | — | — | 13 | | Cetera/Lamm | Chicago Transit Authority | | Columbia 45467 |
| Sept. 1971 | → "I'm a Man" (B-side) | 49 | — | — | 8 | 13 | 8 | 67 | | Kath/Cetera/Lamm | Chicago Transit Authority | | Columbia 45467 |
| July 1972 | "Saturday in the Park" | 3 | 8 | 43 | — | — | 2 | 3 | RIAA: Gold | Lamm/Cetera | Chicago V | "Alma Mater" | Columbia 45657 |
| Oct. 1972 | "Dialogue (Part I & II)" | 24 | — | 91 | — | — | 26 | 17 | | Cetera/Kath | Chicago V | "Now That You've Gone" | Columbia 45717 |
| June 1973 | "Feelin' Stronger Every Day" | 10 | — | 74 | — | — | 12 | 8 | | Cetera | Chicago VI | "Jenny" | Columbia 45880 |
| Sept. 1973 | "Just You 'n' Me" | 4 | 7 | 23 | — | — | 3 | 1 | RIAA: Gold | Cetera | Chicago VI | "Critic's Choice" | Columbia 45933 |
| Feb. 1974 | "(I've Been) Searchin' So Long" | 9 | 8 | 44 | — | — | 5 | 7 | | Cetera | Chicago VII | "Byblos" | Columbia 46020 |
| June 1974 | "Call on Me" | 6 | 1 | — | — | — | 9 | 10 | | Cetera | Chicago VII | "Prelude to Aire" | Columbia 46062 |
| Oct. 1974 | "Wishing You Were Here" | 11 | 1 | 51 | 51 | — | 12 | 9 | | Kath/Cetera | Chicago VII | "Life Saver" | Columbia 10049 |
| Feb. 1975 | "Harry Truman" | 13 | 23 | — | — | — | 16 | 19 | | Lamm | Chicago VIII | "Till We Meet Again" | Columbia 10092 |
| April 1975 | "Old Days" | 5 | 3 | 80 | — | — | 6 | 6 | | Cetera | Chicago VIII | "Hideaway" | Columbia 10131 |
| Aug. 1975 | "Brand New Love Affair (Part I and II)" | 61 | 27 | — | — | — | 65 | 43 | | Kath/Cetera | Chicago VIII | "Hideaway" | Columbia 10200 |
| June 1976 | "Another Rainy Day in New York City" | 32 | 2 | — | — | — | 37 | 33 | | Cetera | Chicago X | "Hope for Love" | Columbia 10360 |
| July 1976 | "If You Leave Me Now" | 1 | 1 | 1 | 1 | 1 | 1 | 1 | RIAA: Platinum | Cetera | Chicago X | "Together Again" | Columbia 10390 |
| March 1977 | "You Are on My Mind" | 49 | 17 | — | — | — | 75 | 56 | | James Pankow | Chicago X | "Gently I'll Wake You" | Columbia 10523 |
| Sept. 1977 | "Baby, What a Big Surprise" | 4 | 8 | 14 | 41 | — | 3 | 4 | | Cetera | Chicago XI | "Takin' It on Uptown" | Columbia 10620 |
| Jan. 1978 | "Little One" | 44 | 40 | — | — | — | 49 | 59 | | Kath | Chicago XI | "Till the End of Time" | Columbia 10683 |
| May 1978 | "Take Me Back to Chicago" | 63 | 39 | — | — | — | 66 | 62 | | Lamm/Chaka Khan | Chicago XI | "Policeman" | Columbia 10737 |
| Oct. 1978 | "Alive Again" | 14 | 39 | 37 | — | — | 11 | 13 | | Cetera | Hot Streets | "Love Was New" | Columbia 10845 |
| Dec. 1978 | "No Tell Lover" | 14 | 5 | 67 | — | — | 10 | 14 | | Cetera/Donnie Dacus | Hot Streets | "Take a Chance" | Columbia 10879 |
| March 1979 | "Gone Long Gone" | 73 | — | — | — | — | 93 | 75 | | Cetera | Hot Streets | "The Greatest Love on Earth" | Columbia 10935 |
| Aug. 1979 | "Must Have Been Crazy" | 83 | — | — | — | — | — | 84 | | Dacus | Chicago 13 | "Closer to You" | Columbia 11061 |
| Oct. 1979 | "Street Player"* | — | — | — | — | — | — | — | | Cetera | Chicago 13 | "Window Dreamin'" | Columbia 11138 |
| July 1980 | "Thunder and Lightning" | 56 | 46 | — | — | — | — | 67 | | Cetera/Lamm | Chicago XIV | "I'd Rather Be Rich" | Columbia 11345 |
| Oct. 1980 | "Song for You" | — | — | — | — | — | — | — | | Cetera | Chicago XIV | "The American Dream" | Columbia 11376 |
| May 1982 | "Hard to Say I'm Sorry" | 1 | 1 | 4 | 4 | 1 | 1 | 2 | ARIA: Gold RIAA: Gold | Cetera | Chicago 16 | "Sonny Think Twice" | Full Moon/Warner 29979 |
| Sept. 1982 | "Love Me Tomorrow" | 22 | 8 | 82 | — | — | 35 | 22 | | Cetera | Chicago 16 | "Bad Advice" | Full Moon/Warner 29911 |
| Jan. 1983 | "What You're Missing" | 81 | — | — | — | — | — | — | | Cetera | Chicago 16 | "Rescue You" | Full Moon/Warner 29798 |
| April 1984 | "Stay the Night" | 16 | — | — | — | — | 47 | 15 | | Cetera | Chicago 17 | "Only You" | Full Moon/Warner 29306 |
| July 1984 | "Hard Habit to Break" | 3 | 3 | 20 | 8 | 3 | 5 | 2 | | Cetera/Bill Champlin | Chicago 17 | "Remember the Feeling" | Full Moon/Warner 29214 |
| Nov. 1984 | "You're the Inspiration" | 3 | 1 | 43 | 14 | 9 | 5 | 4 | | Cetera | Chicago 17 | "Once in a Lifetime" | Full Moon/Warner 29126 |
| Feb. 1985 | "Along Comes a Woman"** | 14 | 25 | — | 96 | — | 17 | 19 | | Cetera | Chicago 17 | "We Can Stop the Hurtin'" | Full Moon/Warner 29082 |
| Aug. 1986 | "25 or 6 to 4" (Newly re-recorded version) | 48 | — | — | — | — | 52 | 46 | | Jason Scheff | Chicago 18 | "One More Day" | Full Moon/Warner 28628 |
| Oct. 1986 | "Will You Still Love Me?" | 3 | 2 | — | — | — | 6 | 4 | | Scheff/Champlin | Chicago 18 | "25 or 6 to 4" (Newly re-recorded version) | Full Moon/Warner 28512 |
| March 1987 | "If She Would Have Been Faithful..." | 17 | 9 | — | — | — | 54 | 16 | | Scheff/Champlin | Chicago 18 | "Forever" | Full Moon/Warner 28424 |
| June 1987 | "Niagara Falls" | 91 | — | — | — | — | — | — | | Scheff/Champlin | Chicago 18 | "I Believe" | Full Moon/Warner 28283 |
| May 1988 | "I Don't Wanna Live Without Your Love" | 3 | 5 | 60 | 127 | — | 4 | 5 | | Champlin | Chicago 19 | "I Stand Up" | Full Moon/ Reprise 27855 |
| Sept. 1988 | "Look Away" | 1 | 1 | — | 77 | — | 1 | 1 | RIAA: Gold | Champlin | Chicago 19 | "Come in from the Night" | Full Moon/ Reprise 27766 |
| Jan. 1989 | "You're Not Alone" | 10 | 9 | — | — | — | 22 | 9 | | Champlin | Chicago 19 | "It's Alright" | Full Moon/ Reprise 27757 |
| April 1989 | "We Can Last Forever" | 55 | 12 | — | — | — | 74 | 53 | | Scheff | Chicago 19 | "One More Day" | Full Moon/ Reprise 22985 |
| Nov. 1989 | "What Kind of Man Would I Be?" | 5 | 2 | — | — | 14 | 4 | 5 | | Scheff | Chicago 19/Greatest Hits 1982-1989 | "25 or 6 to 4" | Full Moon/ Reprise 22741 |
| July 1990 | "Hearts in Trouble" | 75 | — | 77 | — | — | — | 57 | | Champlin | Days of Thunder soundtrack | "Car Building" | DGC 19679 |
| Jan. 1991 | "Chasin' the Wind" | 39 | 13 | — | — | — | 50 | 31 | | Champlin | Twenty 1 | "Only Time Can Heal the Wounded" | Reprise 19466 |
| Apr. 1991 | "Explain It to My Heart" | — | — | — | — | — | — | 107 | | Scheff/Champlin | Twenty 1 | "God Save the Queen" | Reprise 19449 |
| Aug. 1991 | "You Come to My Senses" | — | 11 | — | — | — | 57 | — | | Scheff | Twenty 1 | "Who Do You Love" | Reprise 19205 |
| June 1995 | "Dream a Little Dream of Me" | — | — | — | — | — | — | — | | Scheff/Jade | Night & Day Big Band | | Giant |
| April 1997 | "Here in My Heart" | 59* | 1 | — | — | — | — | — | | Champlin/Scheff | The Heart of Chicago 1967–1997 | | Reprise |
| Oct. 1997 | "The Only One" | — | 17 | — | — | — | — | — | | Lamm/Champlin/Scheff/Lenny Kravitz | The Heart of Chicago 1967–1997 | | Reprise |
| June 1998 | "All Roads Lead to You" | — | 14 | — | — | — | — | — | | Champlin/Lamm/Scheff | The Heart of Chicago 1967–1998 Volume II | | Reprise |
| Oct. 1998 | "Show Me a Sign" | — | 28 | — | — | — | — | — | | Scheff/Champlin | The Heart of Chicago 1967–1998 Volume II | | Reprise |
| Sept. 1999 | "Back to You" | — | — | — | — | — | — | — | | Scheff | Chicago XXVI: Live in Concert | | Chicago Records |
| Feb. 2006 | "Feel" | — | 19 | — | — | — | — | — | | Lamm | Chicago XXX | | Rhino |
| May 2006 | "Love Will Come Back" (featuring Rascal Flatts) | — | 21 | — | — | — | — | — | | Scheff/Rascal Flatts members/Champlin | Chicago XXX | | Rhino |
| June 2008 | "Let's Take a Lifetime" | — | — | — | — | — | — | — | | Scheff | Chicago XXXII: Stone of Sisyphus | | Rhino |
| Dec. 2011 | "My Favorite Things" | — | 9 | — | — | — | — | — | | Lamm | Chicago XXXIII: O Christmas Three | | Chicago Records II |
| Nov. 2019 | "All Over the World" | — | 28 | — | — | — | — | — | | Neil Donell | Chicago Christmas (2019) | | Rhino |
| Dec. 2019 | "Sleigh Ride 2019" | — | 15 | — | — | — | — | — | | Donell | Chicago Christmas (2019) | | Rhino |
| May 2022 | "If This Is Goodbye" | — | 16 | — | — | — | — | — | | Donell/Lamm | Chicago XXXVIII: Born For This Moment | | BMG |
* "Street Player" peaked at #91 on the US R&B chart in December 1979.
* The #59 peak of "Here in My Heart" was on the Hot 100 Airplay chart. The record was not eligible for the Hot 100 at the time, not being released as a retail single.

### Billboard and Cash Box year-end performances

| Year | Song | BB Year-End Position | CB Year-End Position |
| 1970 | "Make Me Smile" | 59 | 60 |
| 1970 | "25 or 6 to 4" | 61 | — |
| 1971 | "Beginnings" / "Colour My World" | 56 | 58 |
| 1972 | "Saturday in the Park" | 76 | 71 |
| 1973 | "Feelin' Stronger Every Day" | 54 | 82 |
| 1973 | "Just You 'N' Me" | — | 62 (1973) 60 (1974) |
| 1974 | "(I've Been) Searchin' So Long" | 73 | 65 |
| 1974 | "Call On Me" | 98 | — |
| 1976 | "If You Leave Me Now" | 48 | 14 |
| 1982 | "Hard to Say I'm Sorry" | 10 | 11 |
| 1984 | "Hard Habit to Break" | 45 | 32 |
| 1985 | "You're the Inspiration" | 37 | 35 |
| 1987 | "Will You Still Love Me?" | 50 | 23 |
| 1988 | "I Don't Wanna Live Without Your Love" | 48 | 40 |
| 1989 | "Look Away" | 1 | — |
| 1990 | "What Kind of Man Would I Be?" | 71 | — |

## Other appearances

| Year | Song | Album |
| 1985 | "Good for Nothing" | We Are the World |

## Videos
### Music videos

List of music videos, with directors, showing year released :
| Year | Video | Director |
| 1976 | "If You Leave Me Now" (Live) | |
| 1978 | "Alive Again" (Live) | |
| 1982 | "Hard To Say I'm Sorry" | |
| 1982 | "Love Me Tomorrow" | |
| 1984 | "Stay the Night" | Gilbert Bettman Jr. |
| 1984 | "Hard Habit to Break" | Leslie Libman |
| 1984 | "You're the Inspiration" | Leslie Libman |
| 1985 | "Along Comes a Woman" | Jay Dubin |
| 1986 | "25 or 6 to 4" | Andy Brenton |
| 1986 | "Will You Still Love Me?" | |
| 1988 | "I Don't Wanna Live Without Your Love" | Paul Boyington |
| 1988 | "Look Away" | |
| 1989 | "You're Not Alone" | Richard Levine |
| 1990 | "Hearts in Trouble" | Michael Bay |
| 1991 | "Chasin' the Wind" | |
| 1991 | "Explain It to My Heart" | |
| 2006 | "Feel" | |
| 2014 | "Now" | |
| 2014 | "More Will Be Revealed" | |
| 2022 | "If This is Goodbye" | |