Chicago Sweepstakes
Found 24 total
Goodreads (eBook) The Lion in the Colosseum Book Giveaway – enter this sweepstakes for a chance to win a free eBook copy of Daniel Amory’s captivating new novel.
Jordan Moore, a young journalist from Chicago, heads to Coastal Point, a small Gulf‑Coast town, to rebuild his career and his life. He’s assigned to uncover the mystery behind the aloof Dale Bowen, but his investigation spirals when he meets Kinsley Hayes, who offers a crucial favor in exchange for an introduction to Bowen. The story blends humor, vulnerability, and intrigue, delivering a perfect mix of laughs and heartfelt moments.
Now also available as an audiobook, this title promises an adventure of a lifetime.
Enter to win, enjoy the free entry, and experience the humor and depth of “The Lion in the Colosseum.”
Win $300 in value – Goodreads (eBook) The Lion in the Colosseum Book Giveaway - Enter Now
Pristine Auction presents the Pristine Auction Bears Gameday Giveaway – a chance to win a coveted NFL collectible.
- One (1) Full‑Size Signed Jaylon Johnson Chicago Bears Helmet – prize is unlocked and awarded only if the Chicago Bears record 3 or more sacks and force at least 1 turnover against the Tennessee Titans.
Ending Date: Saturday at game kickoff. Winner announced August 31, 2026.
Win $350 in value – Pristine Auction Bears Gameday Giveaway - Enter Now
TH Foods Crunchmaster x Chicago Fire Giveaway – enter for a free entry and a chance to win an exciting soccer prize pack. This sweepstakes lets you win premium Chicago Fire experiences and exclusive Crunchmaster swag.
- 2 premium field‑level Chicago Fire tickets
- 2 Chicago Fire jerseys
- 1 Chicago Fire autographed soccer ball
- Bundle of Crunchmaster products & swag
Enter to win before the end date of September 9, 2026.
Don’t miss this giveaway – TH Foods brings you the ultimate fan experience.
Win $1,600 in value – TH Foods Crunchmaster x Chicago Fire Giveaway - Enter Now
Visit Sun Prairie Ultimate Packers Weekend Getaway – Enter for a chance to win an unforgettable football experience. The sweepstakes prize package includes:
- 2 tickets to the Green Bay Packers vs. Chicago Bears game at Lambeau Field
- 1-night stay at the Hilton Garden Inn Sun Prairie
- $100 Buck & Honey’s Sun Prairie gift card
The giveaway ends on August 31, 2026 at 11:59 PM. Free entry, no purchase necessary. Open to eligible participants as specified by the sponsor. Don’t miss your chance to win this ultimate Packers weekend getaway. Visit Sun Prairie.
Win $500 in value – Visit Sun Prairie Ultimate Packers Weekend Getaway - Enter Now
Chicago Bears present the 2026 Chicago Bears Kids Club Gameday Ticket Sweepstakes – a free entry giveaway where you can win an exciting fan‑experience package.
- 4 tickets to one Chicago Bears home game
- 1 parking pass
- $100 Bears Balance
- $100 Pro Shop gift certificate
- 1 Chicago Bears hat
Eight winners will be selected. The sweepstakes ends on September 8, 2026 at 11:59 PM CT. Enter now for your chance to win with the Chicago Bears.
The Ultimate Chicago Weekend Giveaway lets one lucky winner and their crew enjoy a full weekend in the Windy City. Enter by September 3, 2026 for a chance to win a 2‑night stay at The Godfrey Hotel, four tickets to The Color Factory, four Wendella boat tour tickets, four Cycleboat cruise tickets, and a $200 Sweetwater Tavern & Grille gift card (estimated total value $1,000). Open to participants 18+ in the United States who can travel to Chicago. To enter, like, save, follow Sweetwater Chi and tagged partners, and tag a friend in the comments (each tag counts as one entry). This sweepstakes ends on September 3, 2026.
Win $1,000 in value – Sweetwater Tavern & Grille The Ultimate Chicago Weekend Giveaway - Enter Now
College Avenue Student Loans presents the College Avenue Student Loans Ultimate Chicago Fire Experience Sweepstakes – a free entry giveaway where you can win an Ultimate Prize Pack.
- Customized team gear
- Pre‑match experience
- Two (2) field‑level tickets
- $1,000 Visa Gift Card
Enter to win before the sweepstakes ends on August 31, 2026 at 11:59:59 p.m. EDT.
Enter the Giveaway Time from Windy City Chicago for a chance to win a Glow Revival facial treatment at The Spa at Palmer House plus a Dermaflash device. One lucky winner will be announced on August 30, 2026. The prize bundle is valued at approximately $270. To enter, like the post, follow @windy_citychicago and @thespaatpalmerhouse, and tag a friend in the comments. Open to participants 18+ in the United States. This sweepstakes is a great way to refresh your skin and enjoy a premium spa experience. This sweepstakes ends on August 30, 2026.
Win $270 in value – Windy City Chicago Giveaway Time - Enter Now
Enter the Yardbird Picnic Kit Giveaway for a chance to win a $150 Yardbird gift card plus the ultimate picnic kit—insulated cooler pack, blanket, tote bag, T‑shirt, hat and bottle opener. To enter, follow @yardbirdrestaurants and @keninchicago, like the post, tag two friends, and share to your story for a bonus entry. The giveaway ends August 31, 2026. Winners must be 21+ US residents with a public Instagram account. One winner will be announced on Instagram Stories. Good luck!
Win $150 in value – Yardbird Restaurants Picnic Kit Giveaway - Enter Now
Enter to win the Kempersports Frequent Fairways Chicagoland Program Private Course Round Contest for a chance to score a coveted golfing experience. Two lucky winners will be randomly selected from eligible entries received by October 31, 2026. Each winner will receive a prize package worth $800, consisting of one round of golf (greens fees and cart) for up to four players at either The Royal Melbourne Country Club or Hawthorn Woods Country Club, as chosen by the Sponsor. With a total prize value of $1,600, this giveaway is a hole-in-one for golf enthusiasts. Submit your free entry now and take a swing at winning a fantastic golfing prize, courtesy of Kempersports. Free postal mail AMOE in rules.
