Chicago Sweepstakes - Page 1

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Grand prize winners will receive the Barstool VIP Show and Game Package, which includes two meet and greet passes, two game tickets, a two-night hotel stay, and roundtrip flights for two. Two first prize winners will each receive two meet and greet passes, a one-night hotel stay in Chicago, and roundtrip flights for two. One Proper No. Twelve Proper Picks Digital Sweepstakes first prize winner will be selected around November 1, 2025, and another around January 1, 2026. Ten second prize winners will each receive a $50 Barstool merchandise e-gift card, with five winners selected around November 1, 2025, and five more around January 1, 2026.

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The promotion runs across 9 entry periods beginning August 10, 2025, and ending October 11, 2025. Each entry period includes a drawing for 10 winners to receive a $250 NFLShop.com e-Gift Card. In addition to these gift cards, select entry periods feature premium game packages. These include tickets, travel, hotel accommodations, cash stipends, and exclusive experiences for games hosted by teams such as the Washington Commanders, Philadelphia Eagles, Kansas City Chiefs, Denver Broncos (including a London trip), Cleveland Browns, Arizona Cardinals, Detroit Lions, Pittsburgh Steelers, Indianapolis Colts, Green Bay Packers, Houston Texans, San Francisco 49ers, and New England Patriots. Approximate retail values for these packages range from $3,450 to $6,385, depending on the experience. From October 18 through December 27, 2025, the Frito-Lay Epic Experiences Sweepstakes continues with weekly drawings offering ten winners a $250 NFLShop.com e-Gift Card. Each entry period also features premium game packages for matchups hosted by teams including the New York Jets, Minnesota Vikings, Los Angeles Rams, Baltimore Ravens, Las Vegas Raiders, Dallas Cowboys, Seattle Seahawks, Carolina Panthers, Los Angeles Chargers, Buffalo Bills, Jacksonville Jaguars, Chicago Bears, Tennessee Titans, New Orleans Saints, New York Giants, Miami Dolphins, Cincinnati Bengals, Tampa Bay Buccaneers, and Atlanta Falcons. These packages include tickets, travel, hotel stays, cash stipends, and exclusive experiences such as sideline access, VIP tailgates, player meet and greets, and autographed memorabilia, with values ranging from $3,450 to $6,385. The final 3 Frito-Lay Epic Experiences Sweepstakes entry periods feature grand prizes: a Pro Bowl package (ARV $5,050), a Super Bowl LX package (ARV $13,700), and autographed sports memorabilia awarded to 32 winners (ARV $200–$500 per item).

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Miller Lite Football 2025 Instant Win Game. The promotion offers a variety of prizes across several categories. For instant wins, there are 500 grand prizes of fan chain necklaces valued at $19 each and 1,500 first prizes of $10 Venmo payments. The national sweepstakes awards 100 grand prizes, each consisting of a $350 Venmo payment intended for football ticket purchases. In the Steelers keyword sweepstakes, one grand prize includes a trip for four to a 2026 Steelers road game, with airfare, lodging, game tickets, beer for a year, and spending money included. Total approximate value of $4,350. Additionally, 70 ticket prizes are available, each including two game tickets, VIP access to the Miller Lite Renegade Pub, and team swag, with a value of $400. This promotion features a variety of football-themed prizes tied to team-specific keywords. Winners could receive tickets to games for the Saints (5 prizes, ARV $300), Falcons (1 Super Suite prize, ARV $500), Cowboys (1 Party Suite prize, ARV $1,000), Packers (5 Miller Lite Deck ticket prizes, ARV $200, plus chairs, ponchos, and fan chain necklaces), Vikings (3 ticket prizes, ARV $550, plus winter hats, baseball caps, and fan flags), and Bears (5 ticket prizes, ARV $200). Additionally, under the keyword TOUCHDOWN, ten grand prizes are available in the form of $350 Venmo payments intended for football ticket purchases. One winner will receive two tickets to a Lions game (ARV $300), while the keywords CHICAGO and MIDWAY each award five winners with two Bears game tickets (ARV $200 per prize). Under TITANUP, one winner receives tickets to a Titans game (ARV $200). RAVENS offers fifty ponchos (ARV $84) and ninety blankets (ARV $12), and GOBIRDS awards seventy ponchos (ARV $82). The total approximate retail value of all Miller Lite prizes in the promotion is $128,288.

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Step up to the plate and enter the White Sox Baseball Ultimate Fan Sweepstakes! Six amazing prizes are up for grabs across different entry periods:

Entry Period 1: Win 4 tickets to the 2025 Chicago White Sox home opener (March 27, 2025), a pregame field photo, a custom jersey, and a $125 Chicago Team Store gift card. ARV: $350.

Entry Period 2: Enjoy 10 tickets to the White Sox game on June 6, 2025, with VIP access to the private Modelo tailgate, including food and non-alcoholic drinks. (Must be 21+ to enter.) ARV: $500.

Entry Period 3: Score 2 tickets to Lollapalooza, Riot Fest, and a 2025 White Sox regular season home game, plus field passes for the Flo Rida postgame concert. ARV: $500.

Entry Period 4: Take home a collection of exclusive City Connect merchandise. ARV: $400.

Entry Period 5: Win 20 tickets for you and 19 guests to a 2025 White Sox home game in September and the chance to create and name your own hamburger to be sold at the ballpark. ARV: $2,000.

Entry Period 6: Enjoy a 20-person suite for you and 19 guests at a mutually agreed-upon White Sox home game in 2026. ARV: $1,000.

Don’t miss your chance to swing for these incredible prizes—enter now!

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Proximo Spirits Cuervo sweepstakes is offering an exciting array of prizes for lucky winners. Grand Prize 1, awarded to up to two winners, includes a trip for the winner and a guest (age 21 or older) to Guadalajara, Mexico, with departure on May 1, 2025, and return on May 4, 2025. The prize, valued at approximately $4,300, includes round-trip coach airfare, a three-night stay in a standard double-occupancy hotel, a $500 gift card for transportation, meals, and incidentals, and two VIP passes to a festival in the greater Guadalajara area on May 3, 2025. Grand Prize 2, awarded to one winner, features a trip for the winner and a guest to Chicago, IL, departing on July 4, 2025, and returning on July 7, 2025, with an approximate value of $3,800. It includes airfare, a three-night hotel stay, a $200 gift card, and two 2-day VIP passes to a car racing event on July 5 and 6, 2025. Grand Prize 3, also awarded to one winner, offers a trip for the winner and a guest to Los Angeles, CA, departing on August 1, 2025, and returning on August 4, 2025, with an approximate value of $4,600. This prize includes airfare, a three-night hotel stay, a $200 gift card, and two 2-day VIP passes to a music festival on August 2 and 3, 2025. Grand Prize 4, available to one winner, includes a trip for the winner and a guest to Ocean City, MD, departing on September 25, 2025, and returning on September 29, 2025, with an approximate value of $5,150. It features airfare, a four-night hotel stay, a $200 gift card, and two 3-day VIP passes to a music festival from September 26 to 28, 2025. Additionally, up to 20 First Prize winners will receive a Cuervo prize pack consisting of a Bluetooth speaker, a tote bag, and a set of agave drink straws, each valued at $50. All merchandise, flights, and accommodations are subject to availability, and prizes are non-transferable.