Chicago Sweepstakes - Page 2

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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.

Win $7,560 in value – Keebler Spookie Find The Stripes Sweepstakes - 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

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Enter the Margaritaville at Sea + Zac Brown Band National Contest for a chance to win exciting prizes. Up to 27 Market Winners will receive a pair of tickets to see Zac Brown Band live in various cities, including Pittsburgh, New York, Philadelphia, Kansas City, Miami, Greenville, Greensboro, Denver, and Chicago, with ticket values ranging from approximately $339.04 to $694.18. One Grand Prize Winner will receive a prize valued at up to $3,000.00. The contest is open through approximately 12:59 am (ET) on Monday, November 2, 2026. Don't miss this opportunity to win a free prize and experience the thrill of a live concert, courtesy of Margaritaville at Sea. Enter to win now and take a chance at an unforgettable experience with Margaritaville at Sea.

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Enter to win exciting prizes in the Mountain Dew Rock The Mountain Sweepstakes, open to legal residents of IA, IL, IN, KS, MN, MO, NE, SD, and WI, 18+ (19 in NE). The promotion period runs from April 4, 2026, to October 4, 2026. Play the instant win game by scanning the code on participating retailer signage or visiting mountaindewpromos.com/rockthemountain. Limit one play per person, per email, per household per day. Win instant prizes like Mountain Dew Can Coolers, Speakers, Totes, Spotify subscriptions, and gift cards, with a total of 1,200 instant win prizes available. Additionally, be entered into the Grand Prize Drawing for a trip for two to a concert at the United Center in Chicago, IL, with five Grand Prizes available. The total ARV of all prizes is up to $64,066. Pepsi-Cola Company, the Sponsor, reserves the right to modify the promotion. Enter for free and follow the on-screen instructions to play and claim your prize if you win.

Win $63,000 in value – Mountain Dew Rock The Mountain Instant Win Game Sweepstakes - Enter Now