Grammy Awards:

• Best Jazz Vocal Album: Dedicated to You
  

Grammy Nominations:

• Best Jazz Vocal Album: Nightmoves
  
• Best Jazz Vocal Album: Man in the Air
  
• Best Jazz Vocal Album: Flirting With Twilight
  
• Best Jazz Vocal Album: Live in Chicago
  
• Best Jazz Vocal Performance: This Time It's Love
  
• Best Jazz Vocal Performance: The Messenger
  
• Best Jazz Vocal Performance: Close Your Eyes

• Best Instrumental Arrangement Accompanying a Vocalist
  "Dedicated to You" from Dedicated to You
  (Arrangement by Laurence Hobgood)
  
• Best Instrumental Arrangement Accompanying a Vocalist
  "Easy Living" from Flirting With Twilight
  (Arrangement by Kurt Elling and Laurence Hobgood)

DownBeat :

• Critics Poll Winner: Male Vocalist of the Year -- 2000, 2001, 2002, 2003, 2004, 2005, 2006, 2007, 2008, 2009, 2010
  
• Critics Poll Winner: Talent Deserving Wider Recognition -- 1997, 1998, 1999, 2000
  
• Readers Poll Winner: Male Vocalist of the Year -- 2002, 2004, 2006, 2008, 2009

JazzTimes :

• Readers Poll: Male Vocalist of the Year -- 1998, 2000, 2001, 2002, 2008

Jazz Journalists Association :

• Male Singer of the Year -- 2000, 2002, 2006, 2007, 2009, 2010

JazzWeek :

• Vocalist of the Year -- 2006

Académie du Jazz de Paris :

• Prix Billie Holiday: The Messenger

Nightlife Awards:

• Outstanding Jazz Vocalist in a Major Engagement -- 2010

Chicago Music Awards :

• Jazz Record of the Year -- 1997

Rockford Area Music Awards :

• Hall Of Fame Induction -- 2000

Chicago Tribune :

• A Chicagoan of The Year (Arts) -- 1995

Crain's Chicago Business :

• Inductee: 40 under 40 (Who Make a Difference in Chicago Business) -- 1998