Chicago & Styx on The Windy Cities Tour iHeartmedia Sweepstakes

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Enter the Chicago & Styx on The Windy Cities Tour Sweepstakes, presented by iHeartMedia + Entertainment, Inc, for a chance to win an exciting trip for two to see Chicago & Styx live in concert. The grand prize package, valued at $3,000, includes round-trip air transportation, two nights of hotel accommodations, two concert tickets, a $200 gift card for ground transportation, a signed Styx guitar, and an on-stage moment with Chicago during the encore. To enter, visit any participating station website or the iHeartRadio app and complete the entry form between May 18, 2026, and May 24, 2026. Earn bonus entries by listening to Chicago or Styx on the iHeartRadio app. Open to legal residents of the 50 United States and the District of Columbia, 18 years or older. One winner will be randomly selected on or about May 26, 2026. Don't miss this opportunity to win, courtesy of iHeartMedia + Entertainment, Inc.

Win $3,000 in value – Chicago & Styx on The Windy Cities Tour iHeartmedia Sweepstakes - Enter Now