Chicago Sweepstakes
Found 19 total
Enter the Keebler Spookie Find The Stripes Sweepstakes for a chance to win the grand prize and additional prizes. This official Keebler promotion is open only to legal residents of the 50 United States and Washington, DC who are 18 years or older and have a valid email address. Participants may submit up to six entries per household, with each entry counted toward a random drawing. No purchase is required. See the official rules for full details.
The promotion awards prizes totaling an Approximate Retail Value (ARV) of $7,560. The Grand Prize is a 3-day VIP Experience to the Nashville Zoo for four guests. It includes airfare, a two-night hotel stay, a backstage tour, adventure passes, and a $1,000 check, totaling an ARV of $4,260. Six secondary winners receive a one-year family zoo membership and a behind-the-scenes experience. These $550 local prizes apply to zoos in Nashville, Kansas City, Phoenix, Minnesota, Houston, and Chicago.
Win $7,560 in value – Keebler Spookie Find The Stripes Sweepstakes - Enter Now
Goodreads (Print) When No One Else Will Book Giveaway – Enter now for a free entry to win a copy of Amanda Skenandore’s powerful novel When No One Else Will.
In the fall of 1939, while Europe grapples with the outbreak of war, Mimi Lukas wages a private battle in her Chicago neighborhood. Her husband, Stan, once a promising White Sox player, has been sidelined by a broken leg. His hopes of returning to baseball are dwindling along with their savings. As Stan sinks into inertia, Mimi resolves to go back to nursing.
When a friend tells her of a women’s clinic in need of a nurse, Mimi hesitates. Such places are illegal and clash with her religious upbringing. But Dr. Gabler’s office isn’t the dingy establishment Mimi envisioned. The space is clean, bright, and welcoming; the staff is skillful, and patients are treated with dignity and compassion, even as they are sworn to secrecy about what happens within its walls.
Don’t miss this chance to add a thought‑provoking, historically rich story to your bookshelf. Enter the Goodreads giveaway today and discover why Mimi’s courage shines when no one else will.
Win $90 in value – Goodreads (Print) When No One Else Will Book Giveaway - Enter Now
Yelp Chicago presents the Hotel‑Stay Giveaway, giving one lucky winner a complimentary night at the historic Brewhouse Inn & Suites in Milwaukee, WI, plus an invitation to Yelp Wisconsin’s annual Beer Hunt event on September 16. The prize, valued at approximately $200, offers a cozy overnight stay and a fun brewery experience. To enter, follow @yelpchicago, @yelpwisconsin and @brewhouseinn, like the post, and tag a friend in the comments before 11:59 PM CST on September 1, 2026. The winner will be randomly selected on September 2 and notified via DM. Open to U.S. residents aged 18 and older. No purchase necessary. Enter now for a chance to win this unique Milwaukee getaway!. This sweepstakes ends on September 1, 2026.
Win $200 in value – Yelp Chicago Hotel-Stay Giveaway - Enter Now
Enter the Crunchmaster Crackers Giveaway Time for a chance to win four tickets to a Chicago Fire FC October home game and an exclusive on‑field warm‑up experience. One winner will be randomly selected on September 10, 2026. The prize value is estimated at $200. Open to legal U.S. residents aged 18 or older. To enter, follow Crunchmaster Crackers, share the post to your Stories, and comment who you’d bring. Enter now for your shot at this exciting soccer giveaway!. This sweepstakes ends on September 10, 2026.
Win $200 in value – Crunchmaster Crackers Giveaway - Enter Now
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
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
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
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.
Enter to win the Goodreads (Print) The Responsible Party Book Giveaway and discover a captivating tale of resilience and survival. Claire Carusillo's novel follows the legend of the Unsinkable Mounsey Women, from a Liverpudlian poorhouse in WWI to a Lake Michigan lighthouse in 1971 and present-day Chicagoland. With a rich history of improbable survivals, vaudeville success, and complicated women, this book is a must-read. Enter the Goodreads giveaway for a free chance to win and dive into the story of Claire and her descendants as they navigate love, loss, and family secrets. Goodreads brings you this exciting book giveaway, so enter now and take a chance to win The Responsible Party by Claire Carusillo.
Win $675 in value – Goodreads (Print) The Responsible Party Book Giveaway - Enter Now
