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| Award | Artist | Title | Label | Format | Certification Date
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DRAKE | CHICAGO FREESTYLE (FT. GIVEON) | OVO SOUND / REPUBLIC RECORDS | SINGLE | October 24, 2025 |
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SUFJAN STEVENS | CHICAGO | ASTHMATIC KITTY RECORDS | SINGLE | June 14, 2024 |
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CHICAGO | CHICAGO CHRISTMAS: WHAT'S IT GONNA BE SANTA? | RHINO | ALBUM | August 29, 2023 |
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POLO G | WISHING FOR A HERO (FEAT. BJ THE CHICAGO KID) | COLUMBIA | SINGLE | August 17, 2021 |
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CHARLES JENKINS & FELLOWSHIP CHICAGO | AWESOME | INSPIRED PEOPLE | SINGLE | June 29, 2020 |
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MUDDY WATERS / THE ROLLING STONES | LIVE AT THE CHECKERBOARD LOUNGE CHICAGO 1981 | EAGLE VISION | VIDEO LONGFORM | June 11, 2013 |
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CHICAGO | THE BEST OF CHICAGO: 40TH ANNIVERSARY EDITION | RHINO | ALBUM | January 11, 2010 |
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CHICAGO | LIVE IN CONCERT | E1 ENTERTAINMENT | VIDEO LONGFORM | May 15, 2009 |
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STEVE MILLER BAND | LIVE FROM CHICAGO | KOCH | VIDEO LONGFORM | July 24, 2008 |
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MONTEZ DE DURANGO | EN VIVO DESDE CHICAGO | DISA | ALBUM | August 21, 2007 |
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CHICAGO & EARTH, WIND & FIRE | LIVE AT THE GREEK THEATRE | IMAGE ENTERTAINMENT | VIDEO LONGFORM | August 5, 2005 |
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CHICAGO | THE VERY BEST OF: ONLY THE BEGINNING | RHINO | ALBUM | May 18, 2005 |
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GRUPO MONTEZ DE DURANGO | DE DURANGO A CHICAGO | DISA | ALBUM | February 22, 2005 |
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SHANIA TWAIN | UP! LIVE IN CHICAGO | MERCURY NASHVILLE | VIDEO LONGFORM | March 9, 2004 |
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SOUNDTRACK | CHICAGO - THE MUSICAL | VICTOR | ALBUM | February 12, 2004 |
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SOUNDTRACK | CHICAGO | EPIC | ALBUM | October 2, 2003 |
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DAVE MATTHEWS BAND | LIVE IN CHICAGO 12.19.98 | RCA | ALBUM | January 8, 2002 |
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CHICAGO | IF YOU LEAVE ME NOW | COLUMBIA | SINGLE | September 4, 2001 |
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DAVE HOLLISTER | CHICAGO '85...THE MOVIE | DREAMWORKS | ALBUM | February 14, 2001 |
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CHICAGO | CHICAGO XXV (THE CHRISTMAS ALBUM) | CHICAGO RECORDS | ALBUM | December 16, 1999 |
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CHICAGO | HEART OF CHICAGO 1967-1997 | REPRISE | ALBUM | October 16, 1997 |
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CHICAGO | CHICAGO 17 | FULL MOON | ALBUM | May 29, 1997 |
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CHICAGO | GREATEST HITS 1982-1989 | REPRISE | ALBUM | May 13, 1997 |
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CHICAGO | CHICAGO II | COLUMBIA | ALBUM | August 9, 1991 |
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CHICAGO | CHICAGO IX - CHICAGO'S GREATEST HITS | COLUMBIA | ALBUM | August 9, 1991 |
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CHICAGO | IF YOU LEAVE ME NOW | COLUMBIA | ALBUM | August 9, 1991 |
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CHICAGO | 19 | REPRISE | ALBUM | February 1, 1989 |
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CHICAGO | LOOK AWAY (COME IN FROM THE NIGHT) | REPRISE | SINGLE | January 18, 1989 |
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CHICAGO | CHICAGO 18 | FULL MOON | ALBUM | December 1, 1986 |
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CHICAGO | CHICAGO III | COLUMBIA | ALBUM | November 21, 1986 |
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