Chicago Sweepstakes
Found 16 total
Enter to win the Coastal-Carolina Con Exclusive Higher End Door Prizes Giveaway! To celebrate a major milestone, we're giving away 2 VIP Tickets valued at over $100 to the April 4th & 5th show. The prize package includes 2 Exclusive T-Shirts, VIP line access with 1 hour early entry, Exclusive Higher End Door Prizes, 1 FREE Authentication with MAS Chicago, and more. The winner will be announced on February 28th, so enter now for your chance to win this amazing prize.
Win $225 in value – Coastal-Carolina Con Exclusive Higher End Door Prizes Giveaway - Enter Now
Enter to win the Barstool Sports The 2026 St. Patrick’s Day Sweepstakes for a chance to receive an exciting prize package. One lucky winner will be selected to travel to Chicago, IL with two guests and visit the Barstool Sports HQ Office, plus receive a $2,000 stipend for travel. Barstool Sports will determine all aspects of the prize, valued at a unique experience and $2,000. Join Barstool Sports for this incredible giveaway and take a shot at winning the Chicago HQ Prize, courtesy of Barstool Sports.
Win $2,000 in value – Barstool Sports The 2026 St. Patrick’s Day Sweepstakes - Enter Now
Enter to win the GoodReads (Print) Wake Now in the Fire Book Giveaway and discover a thrilling story of resistance against authoritarian power. When a certain book is banned from all Chicago public schools, students rise to challenge the order, organizing walkouts, sit-ins, and social media campaigns. Inspired by the banned book, Persepolis by Marjane Satrapi, they take a stand against oppression. Win a free copy of Wake Now in the Fire by Jarrett Dapier in this exciting GoodReads giveaway and join the conversation about freedom of expression and the power of literature.
Win $25 in value – GoodReads (Print) Wake Now in the Fire Book Giveaway - Enter Now
93.7 The River is turning up the classics with a pair of tickets to see Chicago & Styx live at Toyota Pavilion at Concord on September 4. One lucky winner will score this $100 night of legendary rock. Entries closing August 30 at 11:59 PM.
Win $100 in value – 93.7 The River Tickets to See Chicago & Styx Sweepstakes - Enter Now
Majic 105.7 is giving away two tickets to see Chicago and Styx live at Blossom Music Center on August 5, 2026. One winner will enjoy a night of timeless hits and classic rock energy under the summer sky. Entries close July 26, 2026, at 11:59 PM.
WTAM 1100 is giving away two tickets to see Chicago and Styx live at Blossom Music Center on August 5, 2026. One winner will score a night of legendary rock, unforgettable hits, and summer concert magic. Entries close July 26, 2026, at 11:59 PM.
Enter the Q104.3 Tickets To See Chicago & Styx Sweepstakes for a chance to win a thrilling prize. Q104.3 is giving away two tickets to see the iconic bands Chicago and Styx live at Jones Beach on July 23, 2026, valued at $160. To win this amazing prize, simply enter by July 16 at 11:59 AM ET. Don't miss out on this free entry opportunity to see these legendary bands perform live, courtesy of Q104.3.
Win $160 in value – Q104.3 Tickets To See Chicago & Styx Sweepstakes - Enter Now
Enter the Q104.3 Passes To Welcome To Rockville Sweepstakes for a chance to win a thrilling prize. Q104.3 is giving away two tickets to see Chicago & Styx at Jones Beach on July 23, 2026, valued at $160. Don't miss this opportunity to win - submit your free entry before the deadline on July 16 at 11:59 AM ET. With Q104.3, you could be rocking out to your favorite bands, courtesy of Q104.3.
Win $890 in value – Q104.3 Passes To Welcome To Rockville Sweepstakes - Enter Now
Enter the 93.9 Lite FM Melissa Forman Wants To Send Chicagoland Teachers To Universal Orlando Resort Sweepstakes for a chance to win big. Each month, four qualifying winners will score prizes worth $250, and one lucky grand prize winner will receive a $2,000 Florida getaway, courtesy of Visit Florida. Don't miss your free entry to win - submit yours before the deadline on May 29, 2026, at 11:59 PM CST with 93.9 Lite FM, your gateway to exciting sweepstakes and giveaways from Visit Florida.
Enter the WhiteClaw Chicago Music Venue Tickets Sweepstakes to win an exciting prize package. Twelve lucky winners will each receive a prize package, courtesy of WhiteClaw, including up to two VIP tickets to a 2026 concert or event of their choice at The Salt Shed in Chicago, valued at up to $125 per ticket, plus a WhiteClaw branded item worth up to $100. With a total prize value of up to $350 each and $4,200 overall, this sweepstakes is a must-enter for music fans. Winners must provide 10 business days' notice for event selection, subject to sponsor approval and availability. Don't miss this chance to win with WhiteClaw.
Win $4,200 in value – WhiteClaw Chicago Music Venue Tickets Sweepstakes - Enter Now
