| | | |
| (I've Been) Searchin' So Long | Chicago VII | | 1974 |
| (I've Been) Searchin' So Long | The Heart of Chicago: 1967-1981 | | 2000 |
| 25 or 6 to 4 | The Hit Years - Live | | 2002 |
| 25 or 6 to 4 | Rhino Hi-Five: Chicago | | 2005 |
| 25 or 6 to 4 | Chicago 18 | | 1986 |
| 25 or 6 to 4 | Live in Japan | | 1972 |
| 25 or 6 to 4 | The Heart of Chicago: 1967-1981 | | 2000 |
| 90 Degrees and Freezing | Chicago XXX | | 2006 |
| A Hit by Varese | Live in Japan | | 1972 |
| A Hit By Varese | Chicago V | | 1972 |
| Ain't It Blue? | Chicago VIII | | 1975 |
| Ain't It Time | Hot Streets | | 1978 |
| Aire | Chicago VII | | 1974 |
| Alive Again | The Heart of Chicago: 1967-1981 | | 2000 |
| Alive Again | Hot Streets | | 1978 |
| All Is Well | Chicago V | | 1972 |
| All the Years [#] | Stone of Sisyphus: XXXII | | 2008 |
| Alma Mater | Chicago V | | 1972 |
| Aloha Mama | Chicago 13 | | 1979 |
| Along Comes a Woman | Chicago 17 | | 1984 |
| Already Gone | Chicago XXX | | 2006 |
| Another Rainy Day in New York City | Chicago X | | 1976 |
| Anxiety's Moment [Instrumental] | Live in Japan | | 1972 |
| Anyway You Want | Chicago VIII | | 1975 |
| A Song for Richard and His Friends | Live in Japan | | 1972 |
| Baby, What a Big Surprise | The Heart of Chicago: 1967-1981 | | 2000 |
| Baby, What a Big Surprise | Chicago XI | | 1977 |
| Bad Advice | Chicago 16 | | 1982 |
| Beginnings | The Hit Years - Live | | 2002 |
| Beginnings | Live in Japan | | 1972 |
| Beginnings | The Heart of Chicago: 1967-1981 | | 2000 |
| Beginnings | Chicago Transit Authority | | 1969 |
| Better | Chicago XXX | | 2006 |
| Bigger Than Elvis [#] | Stone of Sisyphus: XXXII | | 2008 |
| Birthday Boy | Chicago XIV | | 1980 |
| Blues in the Night | Night & Day: Big Band | | 1995 |
| Byblos | Chicago VII | | 1974 |
| Call on Me | Chicago VII | | 1974 |
| Caravan | Night & Day: Big Band | | 1995 |
| Caroline | Chicago XXX | | 2006 |
| Chains | Chicago 16 | | 1982 |
| Chasin' the Wind | Chicago Twenty 1 |  | 1991 |
| Chicago | Night & Day: Big Band | | 1995 |
| Child's Prayer | Christmas: What's It Gonna Be, Santa? | | 2003 |
| Child's Prayer | Chicago's First Christmas | | 1998 |
| Christmas Time Is Here | Christmas: What's It Gonna Be, Santa? | | 2003 |
| Christmas Time Is Here | Chicago's First Christmas | | 1998 |
| Colour My World | Rhino Hi-Five: Chicago | | 2005 |
| Colour My World | Live in Japan | | 1972 |
| Come in from the Night | Chicago 19 | | 1988 |
| Come to Me, Do | Chicago XXX | | 2006 |
| Critics' Choice | Chicago VI | | 1973 |
| Cry for the Lost [#] | Stone of Sisyphus: XXXII | | 2008 |
| Darlin' Dear | Chicago VI | | 1973 |
| Devil's Sweet | Chicago VII | | 1974 |
| Does Anybody Really Know What Time It Is? | Live in Japan | | 1972 |
| Does Anybody Really Know What Time It Is? | The Heart of Chicago: 1967-1981 | | 2000 |
| Does Anybody Really Know What Time It Is? | Chicago Transit Authority | | 1969 |
| Does Anybody Really Know What Time It Is? [Free Form Intro] | Live in Japan | | 1972 |
| Don't Get Around Much Anymore | Night & Day: Big Band | | 1995 |
| Dream a Little Dream of Me | Night & Day: Big Band | | 1995 |
| Explain It to My Heart | Chicago Twenty 1 | | 1991 |
| Feel [Horn Section] | Chicago XXX | | 2006 |
| Feel [Hot Single Mix] | Chicago XXX | | 2006 |
| Feelin' Stronger Every Day | Chicago VI | | 1973 |
| Feliz Navidad | Christmas: What's It Gonna Be, Santa? | | 2003 |
| Feliz Navidad | Chicago's First Christmas | | 1998 |
| Follow Me | Chicago 16 | | 1982 |
| Forever | Chicago 18 | | 1986 |
| Free | Live in Japan | | 1972 |
| Free | The Heart of Chicago: 1967-1981 | | 2000 |
| Free Form Guitar | Chicago Transit Authority | | 1969 |
| Gently I'll Wake You | Chicago X | | 1976 |
| God Rest Ye Merry Gentlemen | Christmas: What's It Gonna Be, Santa? | | 2003 |
| God Rest Ye Merry Gentlemen | Chicago's First Christmas | | 1998 |
| God Save the Queen | Chicago Twenty 1 | | 1991 |
| Gone Long Gone | Hot Streets | | 1978 |
| Goodbye | Chicago V | | 1972 |
| Goody Goody | Night & Day: Big Band | | 1995 |
| Hanky Panky | Chicago VII | | 1974 |
| Happy Man | Chicago VII | | 1974 |
| Hard Habit to Break | Chicago 17 | | 1984 |
| Hard to Say I'm Sorry/Get Away | Chicago 16 | | 1982 |
| Harry Truman | Chicago VIII | | 1975 |
| Have Yourself a Merry Little Christmas | Christmas: What's It Gonna Be, Santa? | | 2003 |
| Have Yourself a Merry Little Christmas | Chicago's First Christmas | | 1998 |
| Heart in Pieces | Chicago 19 | | 1988 |
| Here with Me (A Candle for the Dark) [#] | Stone of Sisyphus: XXXII | | 2008 |
| Hideaway | Chicago VIII | | 1975 |
| Holdin' On | Chicago Twenty 1 | | 1991 |
| Hold On | Chicago XIV | | 1980 |
| Hollywood | Chicago VI | | 1973 |
| Hope for Love | Chicago X | | 1976 |
| Hot Streets | Hot Streets | | 1978 |
| I'd Rather Be Rich | Chicago XIV | | 1980 |
| I'm a Man | Chicago Transit Authority | | 1969 |
| I'm a Man | The Hit Years - Live | | 2002 |
| I'm a Man | Live in Japan | | 1972 |
| I Believe | Chicago 18 | | 1986 |
| I Don't Wanna Live Without Your Love | Chicago 19 | | 1988 |
| I Don't Want Your Money | Chicago III | | 1971 |
| If It Were You | Chicago Twenty 1 | | 1991 |
| If She Would Have Been Faithful... | Chicago 18 | | 1986 |
| If You Leave Me Now | Rhino Hi-Five: Chicago | | 2005 |
| If You Leave Me Now | Chicago X | | 1976 |
| If You Leave Me Now | The Heart of Chicago: 1967-1981 | | 2000 |
| In Terms of Two | Chicago VI | | 1973 |
| In the Country | Chicago II | | 1970 |
| In the Mood | Night & Day: Big Band | | 1995 |
| Introduction | Chicago Transit Authority | | 1969 |
| I Stand Up | Chicago 19 | | 1988 |
| It's Alright | Chicago 18 | | 1986 |
| Italian from New York | Chicago VII | | 1974 |
| It Better End Soon: 1st Movement | Chicago II | | 1970 |
| It Better End Soon: 2nd Movement | Chicago II | | 1970 |
| It Better End Soon: 3rd Movement | Chicago II | | 1970 |
| It Better End Soon: 4th Movement | Chicago II | | 1970 |
| Jenny | Chicago VI | | 1973 |
| Jolly Old St. Nicholas [#] | Christmas: What's It Gonna Be, Santa? | | 2003 |
| Just You 'N' Me | Chicago VI | | 1973 |
| Just You 'N' Me | The Heart of Chicago: 1967-1981 | | 2000 |
| King of Might Have Been | Chicago XXX | | 2006 |
| Let's Take a Lifetime [#] | Stone of Sisyphus: XXXII | | 2008 |
| Let's Take a Lifetime [#][*][Demo Version] | Stone of Sisyphus: XXXII | | 2008 |
| Let It Snow! Let It Snow! Let It Snow! | Christmas: What's It Gonna Be, Santa? | | 2003 |
| Let It Snow! Let It Snow! Let It Snow! | Chicago's First Christmas | | 1998 |
| Liberation | Chicago Transit Authority | | 1969 |
| Liberation | The Hit Years - Live | | 2002 |
| Life Is What It Is | Chicago 13 | | 1979 |
| Life Saver | Chicago VII | | 1974 |
| Listen | Chicago Transit Authority | | 1969 |
| Little Miss Lovin' | Hot Streets | | 1978 |
| Little One | Chicago XI | | 1977 |
| Loneliness Is Just a Word | Chicago III | | 1971 |
| Long Lost Friend | Chicago XXX | | 2006 |
| Long Time No See | Chicago VIII | | 1975 |
| Look Away | Chicago 19 | | 1988 |
| Loser With a Broken Heart | Chicago 13 | | 1979 |
| Love Me Tomorrow | Chicago 16 | | 1982 |
| Love Was New | Hot Streets | | 1978 |
| Love Will Come Back | Chicago XXX | | 2006 |
| Lovin' Chains | Chicago XXX | | 2006 |
| Lowdown | Chicago III | | 1971 |
| Lowdown | The Heart of Chicago: 1967-1981 | | 2000 |
| Lowdown [Japanese Version] | Live in Japan | | 1972 |
| Mah-Jong [#] | Stone of Sisyphus: XXXII | | 2008 |
| Mah-Jong [#][*][Demo Version] | Stone of Sisyphus: XXXII | | 2008 |
| Make Me Smile | Rhino Hi-Five: Chicago | | 2005 |
| Make Me Smile | Live in Japan | | 1972 |
| Make Me Smile | The Heart of Chicago: 1967-1981 | | 2000 |
| Mama Mama | Chicago X | | 1976 |
| Mama Take | Chicago 13 | | 1979 |
| Manipulation | Chicago XIV | | 1980 |
| Man to Woman | Chicago Twenty 1 | | 1991 |
| Man vs. Man: The End | Chicago III | | 1971 |
| Mississippi Delta City Blues | Chicago XI | | 1977 |
| Mississippi Delta City Blues | Live in Japan | | 1972 |
| Mongonucleosis | Chicago VII | | 1974 |
| Moonlight Serenade | Night & Day: Big Band | | 1995 |
| Mother | Chicago III | | 1971 |
| Must Have Been Crazy | Chicago 13 | | 1979 |
| Never Been in Love Before | Chicago VIII | | 1975 |
| Niagara Falls | Chicago 18 | | 1986 |
| Night and Day | Night & Day: Big Band | | 1995 |
| No Tell Lover | Hot Streets | | 1978 |
| Nothin's Gonna Stop Us Now | Chicago 18 | | 1986 |
| Now More Than Ever | Live in Japan | | 1972 |
| Now That You've Gone | Chicago V | | 1972 |
| O Come All Ye Faithful | Christmas: What's It Gonna Be, Santa? | | 2003 |
| O Come All Ye Faithful | Chicago's First Christmas | | 1998 |
| Oh, Thank You Great Spirit | Chicago VIII | | 1975 |
| Old Days | Chicago VIII | | 1975 |
| Old Days | The Heart of Chicago: 1967-1981 | | 2000 |
| Once in a Lifetime | Chicago 17 | | 1984 |
| Once or Twice | Chicago X | | 1976 |
| One from the Heart | Chicago Twenty 1 | | 1991 |
| One Little Candle | Christmas: What's It Gonna Be, Santa? | | 2003 |
| One Little Candle | Chicago's First Christmas | | 1998 |
| One More Day | Chicago 18 | | 1986 |
| Only Time Can Heal the Wounded | Chicago Twenty 1 | | 1991 |
| Only You | Chicago 17 | | 1984 |
| Over and Over | Chicago 18 | | 1986 |
| Overnight Cafe | Chicago XIV | | 1980 |
| Paradise Alley | Chicago 13 | | 1979 |
| Plaid [#] | Stone of Sisyphus: XXXII | | 2008 |
| Please Hold On | Chicago 17 | | 1984 |
| Poem 58 | Chicago Transit Authority | | 1969 |
| Poem for the People | Chicago II | | 1970 |
| Policeman | Chicago XI | | 1977 |
| Prelude | Chicago II | | 1970 |
| Prelude (Little One) | Chicago XI | | 1977 |
| Prelude to Aire | Chicago VII | | 1974 |
| Prima Donna | Chicago 17 | | 1984 |
| Prologue, August 29, 1968 | Chicago Transit Authority | | 1969 |
| Questions 67 & 68 | The Hit Years - Live | | 2002 |
| Questions 67 & 68 [Japanese Version] | Live in Japan | | 1972 |
| Questions 67 and 68 | The Heart of Chicago: 1967-1981 | | 2000 |
| Questions 67 and 68 | Chicago Transit Authority | | 1969 |
| Rediscovery | Chicago VI | | 1973 |
| Remember the Feeling | Chicago 17 | | 1984 |
| Reruns | Chicago 13 | | 1979 |
| Rescue You | Chicago 16 | | 1982 |
| Runaround | Chicago 19 | | 1988 |
| Run Away | Chicago 13 | | 1979 |
| Santa Claus Is Coming to Town | Christmas: What's It Gonna Be, Santa? | | 2003 |
| Santa Claus Is Coming to Town | Chicago's First Christmas | | 1998 |
| Saturday in the Park | Chicago V | | 1972 |
| Saturday in the Park | Rhino Hi-Five: Chicago | | 2005 |
| Saturday in the Park | Live in Japan | | 1972 |
| Saturday in the Park | The Heart of Chicago: 1967-1981 | | 2000 |
| Scrapbook | Chicago X | | 1976 |
| Show Me the Way | Hot Streets | | 1978 |
| Silent Night | Christmas: What's It Gonna Be, Santa? | | 2003 |
| Silent Night | Chicago's First Christmas | | 1998 |
| Sing, Sing, Sing | Night & Day: Big Band | | 1995 |
| Sing a Mean Tune Kid | Chicago III | | 1971 |
| Skinny Boy | Chicago VII | | 1974 |
| Skin Tight | Chicago X | | 1976 |
| Sleeping in the Middle of the Bed [#] | Stone of Sisyphus: XXXII | | 2008 |
| Somebody Somewhere | Chicago Twenty 1 | | 1991 |
| Someday (August 29, 1968) | Chicago Transit Authority | | 1969 |
| Something in This City Changes People | Chicago VI | | 1973 |
| So Much to Say, So Much to Give | Live in Japan | | 1972 |
| Song for You | Chicago XIV | | 1980 |
| Song of the Evergreens | Chicago VII | | 1974 |
| Sonny Think Twice | Chicago 16 | | 1982 |
| Sophisticated Lady | Night & Day: Big Band | | 1995 |
| South California Purple | The Hit Years - Live | | 2002 |
| South California Purples | Chicago Transit Authority | | 1969 |
| State of the Union | Chicago V | | 1972 |
| State of the Union | Live in Japan | | 1972 |
| Stay the Night | Chicago 17 | | 1984 |
| Stone of Sisyphus [#] | Stone of Sisyphus: XXXII | | 2008 |
| Stone of Sisyphus [No Rhythm Loop][Alternate Take][#][*] | Stone of Sisyphus: XXXII | | 2008 |
| Street Player | Chicago 13 | | 1979 |
| Take a Chance | Hot Streets | | 1978 |
| Take Me Back to Chicago | Chicago XI | | 1977 |
| Take the "A" Train | Night & Day: Big Band | | 1995 |
| Takin' It on Uptown | Chicago XI | | 1977 |
| The American Dream | Chicago XIV | | 1980 |
| The Christmas Song | Christmas: What's It Gonna Be, Santa? | | 2003 |
| The Christmas Song | Chicago's First Christmas | | 1998 |
| The Greatest Love on Earth | Hot Streets | | 1978 |
| The Inner Struggles of a Man | Chicago XI | | 1977 |
| The Pull [#] | Stone of Sisyphus: XXXII | | 2008 |
| The Road | Chicago II | | 1970 |
| The Show Must Go On [#] | Stone of Sisyphus: XXXII | | 2008 |
| This Christmas [#] | Christmas: What's It Gonna Be, Santa? | | 2003 |
| This Time | Chicago XI | | 1977 |
| Thunder and Lightning | Chicago XIV | | 1980 |
| Till the End of Time | Chicago XI | | 1977 |
| Till We Meet Again | Chicago VIII | | 1975 |
| To Be Free [Instrumental] | Live in Japan | | 1972 |
| Together Again | Chicago X | | 1976 |
| Upon Arrival | Chicago XIV | | 1980 |
| Victorious | Chicago 19 | | 1988 |
| Vote for Me | Chicago XI | | 1977 |
| Waiting for You to Decide | Chicago 16 | | 1982 |
| Wake Up Sunshine | Chicago II | | 1970 |
| We Can Last Forever | Chicago 19 | | 1988 |
| We Can Stop the Hurtin' | Chicago 17 | | 1984 |
| West Virginia Fantasies [Instrumental] | Live in Japan | | 1972 |
| What Can I Say | Chicago 16 | | 1982 |
| What Child Is This? | Christmas: What's It Gonna Be, Santa? | | 2003 |
| What Child Is This? | Chicago's First Christmas | | 1998 |
| What Does It Take | Chicago Twenty 1 | | 1991 |
| What Else Can I Say | Chicago III | | 1971 |
| What Kind of Man Would I Be? | Chicago 19 | | 1988 |
| What You're Missing | Chicago 16 | | 1982 |
| Where Did the Lovin' Go | Chicago XIV | | 1980 |
| Where Were You | Chicago XXX | | 2006 |
| While the City Sleeps | Chicago V | | 1972 |
| White Christmas | Christmas: What's It Gonna Be, Santa? | | 2003 |
| White Christmas | Chicago's First Christmas | | 1998 |
| Who Do You Love | Chicago Twenty 1 | | 1991 |
| Why Can't We | Chicago XXX | | 2006 |
| Will You Still Love Me? | Chicago 18 | | 1986 |
| Window Dreamin' | Chicago 13 | | 1979 |
| Wishing You Were Here | Chicago VII | | 1974 |
| Wishing You Were Here | The Heart of Chicago: 1967-1981 | | 2000 |
| Woman Don't Want to Love Me | Chicago VII | | 1974 |
| You're Not Alone | Chicago 19 | | 1988 |
| You're the Inspiration | Chicago 17 | | 1984 |
| You Are on My Mind | Chicago X | | 1976 |
| You Come to My Senses | Chicago Twenty 1 | | 1991 |
| You Get It Up | Chicago X | | 1976 |
