Chicago Sweepstakes
Found 18 total
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 the SiriusXM Ed Sheeran Sweepstakes for a chance to win an unforgettable prize package. One grand prize winner will receive two floor tickets to see Ed Sheeran live in the city of their choice, with options including Glendale, Nashville, Chicago, and more. The prize also includes round-trip air transportation for two and a two-night hotel stay. The approximate retail value of the prize is $3,500. Don't miss out on this amazing opportunity to see Ed Sheeran perform live - enter the SiriusXM Ed Sheeran Sweepstakes today for your free entry to win.
Win $3,500 in value – SiriusXM Ed Sheeran 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
Enter the Coca‑Cola Match Day Getaway Sweepstakes for a chance to win exciting prizes. The Coca‑Cola Company is giving away a Grand Prize trip for two to a U.S Men’s National Team match in Chicago, IL, valued at $4,500. Other prizes include foosball tables, VISA Prepaid Cards, and soccer balls with tote bags. To enter, visit the Website, use a participating retail location's App, or mail in an entry. No purchase necessary. Open to legal U.S. residents 18+ in the 50 United States and D.C. Sweepstakes runs from March 16, 2026 to April 30, 2026. The Coca‑Cola Company is proud to bring you this sweepstakes, with winners selected in a random drawing on May 8, 2026. Enter now for a free chance to win.
Win $4,500 in value – Coca-Cola Match Day Getaway Sweepstakes - Enter Now
Enter the Culture Pop Noah Kahan Giveaway for a chance to win an unforgettable concert experience. Five lucky winners will receive a prize package of two tickets each to see Noah Kahan perform live at a participating venue, with tickets available at Will Call. Each winner will receive a prize valued at $798.00, with a total prize pool of $3,990.00. Don't miss this opportunity to enter to win and enjoy a free night of music with a friend, courtesy of the Culture Pop Noah Kahan Giveaway.
Participating Venues & Dates:
Boston, MA – Fenway Park 4 Jersey St, Boston, MA 02215
Queens, NY – Citi Field 41 Seaver Way, Queens, NY 11368
Washington, DC – Nationals Park 1500 South Capitol St SE, Washington, DC 20003
Chicago, IL – Wrigley Field 1060 W Addison St, Chicago, IL 60613
Denver, CO – Coors Field 2001 Blake St, Denver, CO 80205
Seattle, WA – T-Mobile Park 1250 1st Ave S, Seattle, WA 98134
San Francisco, CA – Oracle Park 24 Willie Mays Plaza, San Francisco, CA 94107
Los Angeles, CA – Rose Bowl Stadium 1001 Rose Bowl Dr, Pasadena, CA 91103
Win $3,990 in value – Culture Pop Noah Kahan Giveaway - Enter Now
93.7 The River is turning up the classics with a pair of tickets to see Chicago & Styx live at Toyota Pavilion at Concord on September 4. One lucky winner will score this $100 night of legendary rock. Entries closing August 30 at 11:59 PM.
Win $100 in value – 93.7 The River Tickets to See Chicago & Styx Sweepstakes - Enter Now
