Chicago Sweepstakes
Found 19 total
Enter to win the Fanduel Anthony Rizzo Signed Jersey Giveaway, featuring a Chicago Cubs jersey signed by former MLB player Anthony Rizzo, valued at $500. This exciting sweepstakes offers a unique chance to take home a prized piece of sports memorabilia. The giveaway ends at 11:59 PM ET on March 31, 2026, so be sure to submit your free entry before time runs out.
Win $500 in value – Fanduel Anthony Rizzo Signed Jersey Giveaway - Enter Now
Get ready to score big with Windy City Sports Cards Cubs Jersey Giveaway. Enter to win a valuable Chicago Cubs jacket, with an estimated retail value of $180, courtesy of Windy City Sports Cards. This exciting sweepstakes offers a free entry for a chance to take home the prize. Windy City Sports Cards brings you this amazing opportunity to win, so don't miss out - enter now with Windy City Sports Cards.
Win $180 in value – Windy City Sports Cards Cubs Jersey Giveaway - 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
Majic 105.7 is giving away two tickets to see Chicago and Styx live at Blossom Music Center on August 5, 2026. One winner will enjoy a night of timeless hits and classic rock energy under the summer sky. Entries close July 26, 2026, at 11:59 PM.
WTAM 1100 is giving away two tickets to see Chicago and Styx live at Blossom Music Center on August 5, 2026. One winner will score a night of legendary rock, unforgettable hits, and summer concert magic. Entries close July 26, 2026, at 11:59 PM.
