Chicago Southland
Sing Your Way to $100K Winners Announced
Wind Creek Chicago Southland
The moment we've all been waiting for is finally here. After an incredible competition filled with passion, talent, and show-stopping performances, we are thrilled to announce the winners of the Sing Your Way to $100K competition.
Congratulations to Our Grand Prize Winner!
1st Place: Jason Warrior – $100,000 Prize
Meet the Rest of Our Top Finalists!
2nd Place: Jadon Smith – $25,000 Prize
3rd Place: James Reed – $15,000 Prize
4th Place: Joslyn Robinson – $10,000 Prize
5th Place: Kristen Lowe – $7,500 Prize
6th Place: Marian Edwards – $7,500 Prize
A huge THANK YOU to all the talented vocal artists that poured their hearts into this competition and to everyone who supported their favorite singer. This was truly a celebration of Chicago’s music, culture, passion, and talent.
Stay tuned for more exciting opportunities at Wind Creek Casino, and once again, congratulations to the winners for the Sing Your Way to $100K competition.
Congratulations to Our Fan Favorite (Video Audition) Winners!
We are thrilled to announce the winners of the Fan Favorite Competition for Video Auditions — a special segment of the Sing Your Way to $100K singing competition! After an incredible showcase of talent and overwhelming support from fans, the results of the online voting are in.
1st Place: Dion Williams – $5,000 Prize
2nd Place: Marshé Whaley – $2,500 Prize
3rd Place: Afolasade Aina – $1000 Prize
Congratulations to Our Fan Favorite (Live Performance) Winners!
We are thrilled to announce the winners of the Fan Favorite Competition for Live Performance — a special segment of the Sing Your Way to $100K singing competition! After an incredible showcase of talent and overwhelming support from fans, the results of the online voting are in.
1st Place: James Reed – $5,000 Prize
2nd Place: Jason Warrior – $2,500 Prize
3rd Place: Tremel Hoover – $1,000 Prize
Frequently Asked Questions
- Competitors must be members of the Wind Creek Rewards program. Membership is free.
- To enter the Sing Your Way Competition, participants must be 21 years of age or older on or before July 1st, 2025.
- Third parties will judge all rounds of the competition.
- Local personalities, online/social media influencers and/or others will judge the Open Auditions, Preliminary, and Competition Rounds.
- There will be three (3) judges evaluating the competitors and determining who will advance in the competition.
- The judges will remain consistent during each phase of the competition, if possible. Some judges may judge multiple rounds, if necessary.
- The Live Auditions and Video Auditions will be solo performances presented a cappella only (i.e., without other singers, music, or musical instruments). The Preliminary Phase will also be conducted the same way (i.e., solo performances without music or instruments).
- The Competition Rounds will allow background music (tracks only).
- Live Auditions and Video Auditions should last for approximately 2 minutes. (Note: If a video audition exceeds 2 minutes, the judges will not evaluate the additional content.)
- Please remember, the live and video auditions are solo performances that should be conducted without additional singers, music, or musical instruments. The performances should be a cappella only.
- Video submissions should be uploaded to YouTube. Once the upload is completed, the contestant should submit the link to via the online submission tool or via email for posting on the Sing Your Way landing page.
- The bonus vote window for the Fan Favorite Competition will be open from Tuesday, August 5th until Friday, August 8th.
- If voters want to “earn and get” bonus votes to support their competitor of choices, the may activate a Quest received from the Casinoverse app.
- Once received, the voters must earn 25 tier points by playing at Wind Creek Casino Chicago Southland. By earning 25 tier points, the voters will get 5 bonus votes to provide to the competitor of their choice.
- The voters may activate one quest per day during the bonus vote window. The maximum number of bonus votes that may be received is 20.