Chicago Sweepstakes
Found 21 total
Enter to win an OG Chicago Bears Joe Thuney jersey. ERV $150.
Win $150 in value – Just Another Year Chicago: Bears Joe Thuney Jersey Giveaway - Enter Now
Enter the Cake That Chicago Cake Giveaway for a chance to win a stunning custom fondant Chanel Gift Bag Cake. This incredible prize is up for grabs until 2/8/2026. Take a free entry to win this unique cake and make your sweet dreams come true. Join the sweepstakes now and get ready to indulge in a delicious treat, courtesy of the Cake That Chicago Cake Giveaway.
Win $50 in value – Cake That Chicago Cake Giveaway - Enter Now
Get ready to win big with the Bobbles & Lace Chicago Resort Ready Vip Giveaway! Enter to win an incredible prize package valued at over $500, featuring a $100 Bobbles & Lace gift card, a Girls Night Out, a custom spray tan and press-on nails from Glow Out Salons, an 8-class pack and free grip socks from Body Bar Chicago, and a free syringe of lip filler or 25 units of Botox by Aesthetics by Alyssa NP. Don't miss your chance to win - enter by 2/7/2026 for a free entry to this amazing sweepstakes and take home these fantastic prizes!
Win $500 in value – Bobbles & Lace Chicago Resort Ready Vip Giveaway - 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
Bucky’s Got Game is rolling out a lineup of prizes centered around an unforgettable Badgers basketball experience. The grand prize includes two all‑session tickets to the Men’s Conference Basketball Championship in Chicago (March 10–15, 2026), a 3‑night hotel stay, and a $500 travel stipend. Second and third place bring perks too, from Cousins Subs for a year to gift cards for the University Book Store. Entries close February 15, 2026, at 11:59 PM CT.
Win $2,675 in value – Cousins Subs Buckys Got Game Sweepstakes - 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
Enter the Park Hyatt Chicago Parkers Play & Story Set Giveaway for a chance to win an unforgettable family experience. One lucky winner will receive the Parker's Playcation, featuring a two-night suite stay for four at Park Hyatt Chicago, along with a Parker's Play & Story Set and their choice of a tent, kitchen play set, or ball pit. To top it off, a Bed & Brunch board will be delivered to the suite. Don't miss out - enter to win this incredible prize, valued at a memorable stay, before entries close on February 15, 2026, at 11:00 AM CST, courtesy of Park Hyatt Chicago.
Win $450 in value – Park Hyatt Chicago Parkers Play & Story Set Giveaway - 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 MLB Southwest Airlines Chicago Cubs Partnership Launch Sweepstakes for a chance to win one of three unforgettable Cubs experiences, courtesy of MLB Advanced Media, L.P., valued at $2,500. You could score a VIP package at the 2026 Cubs Convention, complete with passes, front-row seating, and a private meet-and-greet. Alternatively, win a trip to Spring Training in Mesa, AZ, with airfare, tickets, and a player meet-up for you and a guest. Or, kick off the season with four tickets to Opening Day at Wrigley Field. Don't miss your free entry to win - submit yours before the deadline on February 19, 2026, at 11:59 PM EST, and you could be cheering on the Cubs in style, thanks to MLB Advanced Media, L.P. and the MLB Southwest Airlines Chicago Cubs Partnership Launch Sweepstakes.
Win $2,500 in value – MLB Southwest Airlines Chicago Cubs Partnership Launch Sweepstakes - Enter Now
