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Sing out. Win prizes.

The Thousand Dollar Sing-Off is Chicago’s newest talent contest, produced by Davenport’s Piano Bar and Cabaret. The Sing-Off will consist of three 3-week competitions, and each will focus on a different genre:


  • Pop: May 1st/8th/15th

  • Musical theatre/Broadway: June 5th/12th/19th

  • Jazz: July 10th/17th/24th


Each week, three judges will award a $1000 first prize, $500 second prize, and a $250 third prize. These competitions will take place in the back room of Davenport’s, all beginning at 8:00pm. May’s competition is hosted by Daryl Nitz & George Howe with 3 judges. June and July’s competition will be hosted by Daryl Nitz & Andrew Blendermann, also with 3 judges.


Admission is $10 for both audience members and participants. Singers will receive a voucher for one drink. All other audience are encouraged to purchase drinks with their servers.


Winners are determined by audience voting, judges' ranking, and participants' talent fit for an upcoming Davenport’s Showcase. May’s winner will be cast in a June 28 show “Soul Sisters: An 80th Birthday Party for Diana Ross, Patti LaBelle, and Gladys Knight.” June’s winner will be cast in an August 25th show “When Kander Met Ebb: Celebrating 60 Years of Friendship.” July’s winner will be cast in a September 6 & 7 show “Sarah & Dinah: A Centennial Celebration.”


Of the 3 first place winners for each month’s competition, the judges will also choose one to receive their own Davenport’s backroom showcase for each genre of Pop, Broadway, and Jazz, in addition to their spotlight in the above showcases.


Submission Guidelines

Contestants should submit a video clip of one whole song, not to exceed four (4) minutes, to Singers may perform with a karaoke track, live accompaniment (including self-accompaniment), or even a cappella.

Singers should also include the following information in their submission email:

  • First and last name

  • Pronouns

  • Age

  • City

  • Performance resume or summary of performance experience

  • Genre (pop, Musical Theatre, jazz) - if submitting for multiple genres, please submit a separate video for each

  • Song title

  • File labeled with full name and song title, e.g. "Daryl Nitz - I Will Survive"


Contestants will be notified via email whether they will be participating and which day they are scheduled to perform. They should then purchase a ticket for their performance date here on Eventbrite and send their sheet music as a pdf (or karaoke track, if using) to

Contest Rules

Submissions are accepted on a rolling basis until the maximum of 20 singers have signed up for each week's competition. Winners (1st, 2nd, or 3rd place) can participate in multiple months/genres but not more than once in the same month (i.e. a first place winner in week 1 of the Pop category can participate in the Jazz category but not in week 2 of the Pop category). 


Singers who don't place 1st, 2nd, or 3rd in any given week may resubmit for future weeks (in the same month or another) as long as the 20 singer threshold has not been reached.


Each week’s competition is limited to 20 singers, and submissions will be accepted on a rolling basis until the 20 slots have been filled. Submissions for all three genres are open immediately.



Are singers required to sing the same song for the competition that they submitted via video?

No, singers may sing whatever they'd like for the live round.

Do singers need to bring sheet music to the live round of the competition?

Singers may use either sheet music for the accompanist, or they can sing from a karaoke/click track. Please make sure tracks are in the correct key and are the length of the full song.

Are winners from any week required to attend other weeks of competition for their genre?

No, winners are not required to attend. Any winner chosen to receive their own show at Davenport's, as well as a spotlight in one of the showcases, will be notified via email.

Is there a grand finale performance for winners from each genre?

No, the weekly competitions are considered single events.

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