It was Elling's first live album, recorded over two nights in 1999 at Chicago's Green Mill jazz club.

[3] Vocalist and composer Jon Hendricks appears on two tracks, "Don't Get Scared" and "Goin' to Chicago."

"The Rent Party" features Elling's interplay with three tenor saxophonists, Von Freeman, Ed Petersen and Eddie Johnson.

Live in Chicago received a Grammy Award for Best Jazz Vocal Album, the fourth nomination in a row since Elling's debut.

[4] Out Takes Album (2000) This 2000s jazz album-related article is a stub.