Chicago Sweepstakes
Found 19 total
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
Enter the Breakfast House Chicago Gift Card Giveaway for a chance to win an unforgettable prize pack. Score 2 tickets to a Cubs game on either Saturday, March 28th, or Sunday, March 29th, and enjoy a $100 gift card to Breakfast House. Don't miss this opportunity to win big - enter to win by 3/24/2026 and take home this exciting prize.
Win $200 in value – Breakfast House Chicago Gift Card Giveaway - Enter Now
Get ready to rock with The Chicago Metal Factory Lamb Of God Tix Giveaway! Enter to win a pair of tickets to see Lamb of God live at the Aragon Ballroom on March 25th, with support from Kublai Kan TX, Fit For An Autopsy, and Sanguisugabogg. This epic concert experience is up for grabs, courtesy of The Chicago Metal Factory. Submit your free entry by March 23rd, 2026, at 11:09 AM CDT for a chance to win this amazing prize.
Win $100 in value – The Chicago Metal Factory Lamb Of God Tix Giveaway - 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.
Enter the Q104.3 Tickets To See Chicago & Styx Sweepstakes for a chance to win a thrilling prize. Q104.3 is giving away two tickets to see the iconic bands Chicago and Styx live at Jones Beach on July 23, 2026, valued at $160. To win this amazing prize, simply enter by July 16 at 11:59 AM ET. Don't miss out on this free entry opportunity to see these legendary bands perform live, courtesy of Q104.3.
Win $160 in value – Q104.3 Tickets To See Chicago & Styx Sweepstakes - Enter Now
