Chicago Sweepstakes
Found 21 total
Get ready to win big with the T-Mobile Tuesdays Sweepstakes. Enter now for a chance to take home an epic prize: a 5-night trip to Chicago, IL, to attend the 2026 Lollapalooza Music Festival. The Grand Prize package includes 4-day VIP Tickets, round-trip air travel, accommodations, and a $2,888.45 check for expenses, with a total ARV of $9,631.43. To attend the Festival, winner and guest must travel between July 29, 2026, and August 3, 2026. Don't miss this opportunity to win big - enter the T-Mobile Tuesdays Sweepstakes for free and make your music festival dreams come true with T-Mobile.
Win $9,631 in value – T-Mobile Tuesdays Sweepstakes - Enter Now
Get ready to score big with the CF Montreal VIP Experience (Tanguay Lounge) Contest. Enter to win two (2) exclusive VIP tickets to the Tanguay Lounge at Saputo Stadium for the exciting match between CF Montreal and Chicago. Don't miss this opportunity to win a prize and experience the thrill of the game in style. Free entry is available until April 30, 2026, at 11:59 PM (ET), so enter now for your chance to win this amazing prize.
Win $1,000 in value – CF Montreal VIP Experience Tanguay Lounge Contest - Enter Now
Enter to win the V&v Supremo® Chicagoland “The Biggest Soccer Event Of The Year” Sweepstakes for a chance to score amazing prizes. Ten lucky winners will receive prizes totaling approximately $8,533.80. Two First Prize winners will get tickets to see Argentina vs. Algeria, worth $2,791.90, plus $200 in V&V Supremo® food coupons. Three Second Prize winners will receive a YETI® cooler and $150 in coupons, while five Third Prize winners will get an authentic official jersey and $100 in coupons. Sweepstakes ends at 11:59 p.m. CT on May 24, 2026. Enter now for a free chance to win with V&V Supremo®.
Enter the Kroger Superfan Sweepstakes for a chance to win exciting prizes. Twenty lucky winners will receive two tickets to a 2026 Texas Rangers MLB regular season home game, with eligible games including matchups against the Athletics, Chicago Cubs, Kansas City Royals, and more. Each prize has an Approximate Retail Value of $595, with a total ARV of $11,900. Don't miss this opportunity to win free tickets to a thrilling baseball game - enter to win today and become a part of the action with the Kroger Superfan Sweepstakes.
Win $11,900 in value – Kroger Superfan Sweepstakes - Enter Now
Enter to win the GoodReads (Print) Strangers Behind Closed Doors Book Giveaway and discover a thrilling mystery. Catherine Adel West's novel follows Giovanni Mason, a determined concierge at the luxurious Ivory Hotel in Chicago, as she reunites with her former best friend, only to become the prime suspect in her disappearance. With the help of beleaguered Detective Redding Stark, Giovanni must navigate a complex web of power and privilege to clear her name. Enter this free giveaway for a chance to win a print copy of this gripping book.
Win $19 in value – GoodReads (Print) Strangers Behind Closed Doors Book Giveaway - Enter Now
Enter the Snooze Eatery SnoozeFest Pancake Flight Sweepstakes for a chance to win a trip for two to Lollapalooza 2026 in Chicago, IL. The grand prize includes a private jet flight, luxury hotel accommodations, general admission tickets, and access to the Tito's VIP experience. No purchase necessary to enter or win. The sweepstakes is open to legal residents of the US, excluding FL and NY, who are 21 or older. Enter by uploading a purchase receipt from Snooze Eatery or through the free, alternate method of entry. Limit one entry per person per day. Sweepstakes runs from April 15, 2026 to June 30, 2026. Sponsored by Snooze Import Export LLC.
Win $31,350 in value – Snooze Eatery SnoozeFest Pancake Flight Sweepstakes - Enter Now
Enter the One Country Windy City Smokeout Flyaway Experience Sweepstakes for a chance to win a prize package valued at $4,500. The sweepstakes is open to U.S. and Canadian residents, excluding Quebec, who are at least 18 years old. No purchase is necessary to enter or win. One winner will receive a flyaway experience to the Windy City Smokeout in Chicago, including round-trip airfare, a five-night hotel stay, VIP experience tickets, meet and greets, and a merchandise bundle. To enter, visit www.onecountry.com or use the free methid linked in the rules portion. The sweepstakes runs from March 17, 2026, to June 15, 2026, and the winner will be announced around June 30, 2026. One Country is the sponsor and prize provider of this exciting giveaway.
Win $4,500 in value – One Country Windy City Smokeout Flyaway Experience Sweepstakes - Enter Now
Enter the Corona The Music Festivals Sweepstakes for a chance to win exciting prizes. The sweepstakes offers multiple prizes, including a pair of VIP admission tickets to the 2026 Suenos Chicago Music Festival and a $1,000 e-check, with an approximate retail value of $2,798. Other prizes include general admission tickets to the festival and Corona-branded merchandise. To enter, visit CBISweeps.com/CoronaMusicFestChi by 11:59 PM ET on the entry deadlines of 5/11/26 or 6/1/26. Random drawings will take place on 5/12/26 and 6/2/26. Don't miss this free entry opportunity to win big with Corona.
Win $2,798 in value – Corona The Music Festivals Sweepstakes - Enter Now
Enter to win the Sippers By 99 Festival Sweepstakes, a thrilling giveaway that could send you and a guest to a 2026 Live Nation-produced festival of your choice. The prize package, valued at approximately $4,000, includes two 2-day VIP tickets, round-trip air transportation, a double occupancy hotel room, and a $200 pre-paid cash card. Choose from participating festivals like Beyond Wonderland in Chicago, Day Trip in Long Beach, or Lost in Dreams in Los Angeles. To be eligible, you and your guest must be at least 21 years old and comply with all festival and travel requirements. Travel must take place by July 12, 2026. Enter now for a chance to win this unforgettable experience, courtesy of Live Nation.
Win $4,000 in value – Sippers By 99 Festival Sweepstakes - Enter Now
Get ready to win big with Cheyenne Cigars' exciting Cheyenne Cigars Windy City Sweepstakes. As a valued member of the Cheyenne Cigars website, you can enter to win a fantastic Chicago, IL Trip Package worth $3,500.00. To participate, simply log into your account at https://www.cheyennecigars.com, follow the instructions, and click the "Enter" button to submit your entry. You can also enter by emailing [email protected] with your required information. The sweepstakes is open to legal residents of the 50 United States (excluding CA, MA, MI, and VA) and DC, who are at least 21 years old. The entry period runs from March 20, 2026, to May 18, 2026. One lucky winner will be selected through a random drawing on or about May 25, 2026. Don't miss your chance to win - enter the Cheyenne Cigars Windy City Sweepstakes today and you could be headed to Chicago courtesy of Cheyenne Cigars.
Win $3,500 in value – Cheyenne Cigars Windy City Sweepstakes - Enter Now
