• Wind Creek Chicago Southland will host the popular singing competition, Sing Your Way to $100K
• Roger Kuehn, Wind Creek Chicago Southland's Executive Vice President and General Manager, speaks about Chicago's artistic legacy
• Open for pre-registration, the singing competition invites vocalists from the Chicagoland area and promises a top prize of $100,000

The premium gaming, hospitality and entertainment resort in Chicago Southland, Wind Creek Chicago Southland, announced that a live, multi-phase singing competition, awarding a top prize of $100,000, is open for pre-registration.

The venue is bringing the famous Sing Your Way to $100K competition, calling all vocalists across the Chicagoland area.

Sing Your Way to $100K arrives at Wind Creek Chicago Southland

Wind Creek Casino's decision to host the exciting music competition comes after Sing Your Way to $100K launched successfully at Magic City Casino in Miami, Florida, earlier this year.

At the time, Albert Pedroso emerged as the big winner, taking home the competition's grand prize of $100,000.

The arrival of Sing Your Way to $100K to Wind Creek Chicago Southland represents the first regional installment of the popular competition.

It complements the venue's list of entertainment activities, promising exceptional experiences with its grand final planned near the end of August.

John Enriquez, Magic City Casino's Executive Vice President and General Manager, commented on the topic, Casino Guru News learned from a press release.

"We knew from the start that Sing Your Way to $100K had the potential to become something much bigger than a one-time event," he explained.

Finally, Enriquez said: "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."

Roger Kuehn, Wind Creek Chicago Southland's Executive Vice President and General Manager, added: "Chicago's artistic legacy runs deep—from its music and theater to the everyday voices that shape its neighborhoods."

He explained that the new live singing competition will give local talent a chance to win a huge prize and shine.

In conclusion, Kuehn added that the hotel and casino resort is excited to grow its entertainment offering while helping local communities.

The popular singing competition is already open for pre-registration

The multi-phase singing competition is already open for pre-registration.

Interested contestants are encouraged to join Sing Your Way to $100K by signing up at singyourwaychicago.com. It's important to note that contestants need to be aged 21 and older to enter the competition.

Besides in-person, video auditions are also going to be held.

Moreover, contestants will be performing in front of live audiences and a panel consisting of media personalities and powerhouse Chicago radio hosts.

Sing Your Way to $100K consists of Qualifying Round, Preliminary Round, Quarterfinals, Semifinals and a Finale that will see the top six finalists perform live.

The exciting Finale will be held on Saturday, August 23, 2025, at Wind Creek and the winner of the competition will take home the grand prize of $100,000.

A prize of $25,000 and $15,000 would be collected by the contestants who take second and third place.

The contestant who comes fourth will win $10,000, while the ones in fifth and sixth place will win $7,500 each.

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