Chicago Sweepstakes
Found 27 total
Enter the Old Chicago Gift Card Giveaway for a chance to win a $100 prize and treat a deserving loved one. This exciting sweepstakes is open until Monday, May 10, so be sure to enter to win your gift card from Old Chicago.
Win $100 in value – Old Chicago Gift Card Giveaway - Enter Now
Enter to win The Chicago Cubs Grand Slam Getaway Fueled By Omaha Steaks Sweepstakes for a chance to score an unforgettable prize package. Two Grand Prizes are up for grabs, each valued at $4,900. Winners will receive a trip for two to Chicago, Illinois, including round-trip airfare, two-night hotel accommodations, and tickets to a Chicago Cubs home game on July 4, 2026, at Wrigley Field. They'll also get Chicago Cubs jerseys, a $100 Uber Gift Card, and a $100 pre-paid bank gift card. Plus, enjoy Omaha Steaks for a Year with four shipments of the Triple Crown Combo. The total prize value is $9,800. Don't miss your chance to win - enter by Sunday, June 7, 2026, at 11:59 PM CST.
Win $9,800 in value – Chicago Cubs Grand Slam Getaway Fueled By Omaha Steaks Sweepstakes - Enter Now
Enter to win the Chicago Makeup Artist Makeup Products / Hair Products / Parfumes Giveaway for a chance to take home amazing prizes. This exciting sweepstakes offers a wide range of goodies, including makeup products, hair products, and perfumes. The giveaway is open until 5/9/2026, so be sure to enter for your free chance to win.
Enter the Lagunitas Brewing Salt Shed Sweepstakes for a chance to win a premium experience. Each winner will receive a prize package with an approximate retail value of $1,750, including two premium concert tickets at Salt Shed in Chicago, a $250 Lagunitas merchandise gift card, and a $1,000 gift card for transportation, lodging, and incidentals. Enter to win this exciting sweepstakes and get ready for an unforgettable experience with Lagunitas Brewing.
Win $5,250 in value – Lagunitas Brewing Salt Shed Sweepstakes - Enter Now
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
Get ready to escape to Chicago with the Chicago City Escape EMC2 Hotel Autograpgh Collection Sweepstakes. Enter to win a grand prize valued at $1550, featuring a 3-night stay at the EMC2 Hotel, Autograph Collection, and a $350 resort credit. Don't miss your chance to win this incredible prize, courtesy of Ecommerce Advisors. The sweepstakes ends on 6/7/2026 at 11:59 pm EDT, so submit your free entry now and take a shot at this amazing getaway with Ecommerce Advisors.
Win $1,550 in value – Chicago City Escape EMC2 Hotel Autograpgh Collection Sweepstakes - Enter Now
Enter the iHeartRadio Trip to see Zac Brown Band on the Love & Fear Tour Sweepstakes for a chance to win an unforgettable trip for two to see Zac Brown Band live in concert. The grand prize package includes round-trip air transportation, two nights of hotel accommodations, two tickets to the show on November 21, 2026, in Chicago, Illinois, a $200 gift card for ground transportation, and a Keep Me in Mind VIP Package with exclusive merchandise and perks. Don't miss out on this amazing opportunity to win a prize valued at over $[not specified]. Enter to win before the sweepstakes ends on May 10, 2026, at 11:59:59 p.m. ET.
Enter the Campbell's Pokémon Instant Win Game for a chance to win exciting prizes. No purchase necessary to enter or win. The promotion is open to legal residents of the 50 United States, including DC, who are at least 18 years old. Employees of Campbell Snacks, the sponsor, and its affiliates are not eligible. The promotion period runs from May 1, 2026, to September 13, 2026. To enter, visit the website and submit an official entry form with required information. Limit one entry per person per day. Three Grand Prizes will be awarded, each consisting of a Pokémon Family Adventure package with a trip to the Chicago Field Museum, worth $6,650. Additionally, there are Instant Win Game prizes, including Pokémon backpacks, plush dolls, and free Goldfish Crackers. Total ARV of all prizes is $42,669.50. Enter now for a chance to win. Campbell's is the sponsor of this promotion, and all prizes will be awarded and fulfilled by them.
Win $42,669 in value – Campbell’s Pokemon Instant Win Game Sweepstakes - Enter Now
Enter the Verizon x FIFA Flyaway from Chicago to FIFA World Cup 2026 Sweepstakes for a chance to win an exciting prize package. Seven lucky winners will receive a round-trip flight from Chicago to attend a FIFA World Cup 2026 match, along with a guest, plus two match tickets, a two-night hotel stay, and $750 in rideshare gift cards. The approximate retail value of each prize is up to $7,950, with a total value of all prizes reaching up to $55,650. Winners will be assigned a match based on the random drawing order and will travel to the match city a day prior to the event and depart a day after.
Enter the Blue Moon White Sox Batting Practice Sweepstakes for a chance to win an exclusive experience. The sweepstakes, sponsored by Molson Coors Beverage Company USA LLC, begins on April 27, 2026, and ends on July 12, 2026. To enter, visit bluemoonbrewingcompany.com/whitesox, submit your date of birth and ZIP Code, and complete the registration form. You could be one of 55 grand prize winners to receive an invitation for yourself and a guest to attend a Chicago White Sox batting practice at Guaranteed Rate Field on September 23, 2026, valued at $100. Open to legal residents of Illinois and selected ZIP codes in Indiana, 21 years or older. See official rules for details. Molson Coors Beverage Company USA LLC is the sponsor of this sweepstakes, and Merkle Inc. is the administrator.
Win $5,500 in value – Blue Moon White Sox Batting Practice Sweepstakes - Enter Now
