Chicago Sweepstakes

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880 Ched All-Star Experience in Chicago: One (1) Grand Prize trip for two (winner and guest) to the 2027 MLB® All-Star Week in Chicago, Illinois (July 12–13, 2027). - Grand Prize includes round‑trip airfare to a Chicago, IL area airport, three (3) nights hotel accommodations in Chicago, two (2) tickets to the Home Run Derby (July 12) and the All-Star Game (July 13), and spending money (amount TBD). Entry period ends October 23, 2026, at 3:48 PM MST.

Win $15,000 in value – 880 Ched All-star Experience In Chicago - Enter Now

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WTTW 2026 Be a Winner Sweepstakes offers approximately 74 prizes, including:

- Grand Prize: 2027 Subaru Crosstrek Hybrid — $36,000

- Road Scholar Kenya & Tanzania Safari for 2 — $21,800

- Oscar Isberian Rugs hand‑woven rug — $6,500

- The Barn on North private event for up to 50 guests — $5,000

- Fitness Formula Clubs 1‑year Signature Membership + 3 personal‑training sessions — $2,718

- Carnivale Chicago private party — 2 prizes, $2,500 each

- Home Carpet One cabinet gift certificate — $2,500

- Grand Hotel Mackinac Island stay — $900

- Edgewater Candles private candle‑making class — 4 prizes, $700 each

- Fleet Feet Chicago gift certificate + training voucher — $650

- Skydeck Chicago private Pie in the Sky dinner — $600

- Garrett Popcorn Family Tin + $500 eGift Card — $562

- Numerous additional restaurant, entertainment, fitness, travel, home, membership and gift‑card prizes

- Spring Early Bird prizes (2): Walla Walla Deluxe Wine Touring Package for 2 — $3,899 each

- Fall Early Bird prize: Weber Summit Smart Gas Grill — $5,299

- Bonus Prize: $10,000 gift card + in‑home design consultation — $10,100

ARV: $121,752 USD.

Ending Date: October 26, 2026.

*Free AMOE by postal mail. 

Win $121,752 in value – WTTW 2026 Be a Winner Sweepstakes - Enter Now

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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.

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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

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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

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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. 

Win $1,600 in value – Kempersports Chicagoland Program Private Course Round Contest - $1600 Value - Enter Now