Wind Creek Casino & Hotel Brings $100K Singing Competition to Chicagoland This Summer

Multi-phase music competition invites local talent to compete live for $165,000 in prizes at newly opened resort and casino

EAST HAZEL CREST, Ill., July 2, 2025 /PRNewswire/ -- Wind Creek Casino & Hotel, located in the Chicago Southland, is calling all vocalists to the stage with Sing Your Way to $100K, a live, multi-phase singing competition offering a $100,000 cash grand prize and more than $165,000 in total cash rewards. Pre-registration is open now, and interested contestants are encouraged to sign up now at singyourwaychicago.com to secure their spot. The competition kicks off this month with in-person and video auditions and culminates in a high-energy finale on Saturday, August 23, 2025.

Open to solo vocalists aged 21 and older, the competition is free to enter and offers a major platform for undiscovered and emerging talent across the Chicagoland area. Contestants will perform live before audiences and a panel of powerhouse Chicago radio and media personalities, including WGCI's Leon Rogers, Tone Kapone, Zach Boog, and Keke Hampton; KISS FM's Paulina Roe; B96 and 104.3 Jams' Moug; 104.3 Jams hosts Jen BT and Sean "Sonic" Leckie; Qué Buena's Johnny "Perro" Orta; and Amor 106.7's Vicky Aguilera.

"Chicago's artistic legacy runs deep—from its music and theater to the everyday voices that shape its neighborhoods," said Roger Kuehn, Executive Vice President and General Manager of Wind Creek Chicago Southland. "Sing Your Way to $100K is our way of honoring that spirit—by giving local talent a stage and a moment to shine. As the newest resort in the region, we're proud to build a home for entertainment that feels both elevated and rooted in the community we serve."

Competition Overview

Pre-registration: Contestants can now pre-register for live or video auditions at singyourwaychicago.com. Priority will be given to those who register in advance. Walk-up participants may be allowed to audition if space permits.

Contest Rounds: To qualify, contestants must audition either in person or by submitting a video online. Live auditions will be held on-site at Wind Creek Chicago Southland and judged by a panel of Chicago media personalities and influencers. Contestants who advance from the Qualifying Round will move through the Preliminary Round, Quarterfinals, Semifinals, and Finale.

Grand Finale: The top six finalists will perform live at Wind Creek Chicago Southland on Saturday, August 23, 2025, with winners announced that evening.

Grand Prize: $100,000 cash will be awarded to the first-place winner, with additional cash prizes of $25,000 for second place, $15,000 for third, $10,000 for fourth, and $7,500 each for fifth and sixth place.

Fan Favorite Competition: Contestants may also enter separate fan-favorite contests by uploading performances and encouraging engagement via social media and on-site at the resort. The top-voted performers of these competitions have the ability to be awarded additional prizes. For more information on the Fan Favorite Competitions, please visit singyourwaychicago.com.

Following its successful premiere earlier this year at Magic City Casino in Miami, where, Albert Pedroso was awarded the $100,000 grand prize, Sing Your Way to $100K is now expanding to the Midwest—bringing its high-stakes energy, star-powered judges, and community celebration to Wind Creek Hospitality's newly opened property just south of downtown Chicago. The competition marks the first regional installment of what is quickly becoming one of Wind Creek's most exciting entertainment initiatives.

"We knew from the start that Sing Your Way to $100K had the potential to become something much bigger than a one-time event," said John Enriquez, Executive Vice President and General Manager of Magic City Casino. "The talent, the energy, and the community response in Miami far exceeded our expectations—and it's incredibly exciting to see that momentum carry into the Chicago market. We're proud to see Wind Creek Chicago Southland take the stage next and continue building this into a signature experience for Wind Creek properties nationwide."

To register, view full rules, or submit an audition video, visit singyourwaychicago.com.

About Wind Creek Hospitality
Wind Creek Hospitality is an authority of the Poarch Band of Creek Indians, the only federally recognized Indian Tribe in the state of Alabama. Wind Creek Hospitality manages the Tribe's gaming facilities including: Wind Creek Aruba, Wind Creek Atmore, Wind Creek Bethlehem, Wind Creek Chicago Southland, Wind Creek Curacao, Wind Creek Montgomery, Wind Creek Wetumpka, Casinoverse, Magic City Casino in FL, as well as racetracks in Alabama and Florida. Visit www.windcreek.com for more information.

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SOURCE Wind Creek Hospitality