Chicago Sweepstakes
Found 26 total
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
Old Chicago is spreading the excitement with a Pizza Party prize: three large specialty pizzas of your choice, two Cookizzas, and a garden or Caesar salad. The contest ends on Wednesday, February 4, at 11:59 pm.
Win $55 in value – Old Chicago Super Bowl Party 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 Bucky’s Got Game Sweepstakes - Enter Now
Enter the Kaylee Jo Flores Valentines Day Giveaway for a chance to win a $200 gift card courtesy of Kaylee Jo Flores and Offshore Spa Chicago. This exciting sweepstakes offers a free entry to win a valuable prize. The winner will be announced on Tuesday, February 3, 2026. Don't miss this opportunity to win with Kaylee Jo Flores and Offshore Spa Chicago.
Win $200 in value – Kaylee Jo Flores Valentines Day Giveaway - Enter Now
Katie O’ Weddings & Events is partnering with Offshore Spa Chicago to give away a $100 Primark gift card as part of the Galentine’s celebration benefiting Girls Inc. The winner will be announced on Monday, February 2, 2026, at 7 PM.
Win $100 in value – Katie OWeddings & Events Galentines Day Giveaway - Enter Now
Enter Jewel-Osco's Elevate Every MOMent Sweepstakes - Indiana for a chance to win exciting prizes. Each lucky winner will receive two tickets to Jewel-Osco's exclusive Elevate Every MOMent event on February 12, 2026, at The Peninsula Chicago, with a prize value of $400. Jewel-Osco is giving away this amazing opportunity to elevate your experience, so enter to win and make unforgettable memories, courtesy of Jewel-Osco.
Win $8,800 in value – Jewel-Osco’s Elevate Every MOMent Sweepstakes - Indiana - Enter Now
Enter to win exciting prizes in Jewel-Osco's Elevate Every MOMent Sweepstakes - Illinois. Jewel-Osco is giving away tickets to its exclusive event, where winners will receive two tickets to Elevate Every MOMent on February 12, 2026, at The Peninsula Chicago, with each prize valued at $400. Join Jewel-Osco for a chance to win this incredible prize, courtesy of Jewel-Osco.
Win $8,800 in value – Jewel-Osco’s Elevate Every MOMent Sweepstakes - Illinois - Enter Now
Enter to win exciting prizes in Jewel-Osco's Elevate Every MOMent Sweepstakes - Iowa. By participating, you could win a fantastic prize package, courtesy of Jewel-Osco, consisting of two tickets to the exclusive Elevate Every MOMent event on February 12, 2026, at The Peninsula Chicago, valued at $400. Join Jewel-Osco's sweepstakes for a free entry to win this incredible prize.
Win $8,800 in value – Jewel-Osco’s Elevate Every MOMent Sweepstakes - Iowa - Enter Now
Enter the Credit Union 1 UIC Basketball Fan Experience Sweepstakes for a chance to win an unforgettable experience, courtesy of Credit Union 1, the Official Banking Partner of the University of Illinois at Chicago. Two exciting prizes are up for grabs: Prize 1, valued at $300, includes tickets to the UIC vs. Belmont men's basketball game, and Prize 2, valued at $175, offers tickets to the UIC vs. Evansville women's basketball game. With a total prize value of $475, two lucky winners will enjoy the ultimate game experience at Credit Union 1 Arena. Don't miss this free entry opportunity to win big with Credit Union 1.
Win $475 in value – Credit Union 1 UIC Basketball Fan Experience 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
