Chicago Sweepstakes
Found 24 total
Enter The Secret Fan Club x AT&T WNBA-All Star 2026 Sweepstakes for a chance to win an unforgettable trip to Chicago, IL. The Grand Prize includes a 2-day/1-night getaway for you and a guest to attend the WNBA All-Star Game on July 25, 2026, with round-trip airfare, hotel accommodations, two Game tickets, a $200 gift card for ground transportation, and $1,320 to help with prize taxes. The total prize value is $5,720.
Win $5,720 in value – Secret Fan Club x AT&T WNBA-All Star 2026 Sweepstakes - Enter Now
Get ready to win big with the Jewel-Osco Party the USA Sweepstakes, celebrating 250 years in style. Enter to win an incredible prize package worth over $3,800, featuring a two-night hotel stay at the Sable Hotel Navy Pier, a dinner cruise experience, Navy Pier Passport, Centennial Wheel Ride access, 360 Chicago Observation deck tickets, a family-sized tin of Garrett Popcorn, and a $250 Jewel-Osco Gift Card. Plus, every entry supports Operation Support Our Troops. Jewel-Osco is giving away this amazing prize package to lucky winners, so enter now for your chance to win and support a great cause with Jewel-Osco.
Win $3,800 in value – Jewel-Osco Party the USA Sweepstakes - 5 Winners - Enter Now
Enter the Carvana 2026 Ultimate All-Star Soccer Experience Giveaway for a chance to win an unforgettable prize package. Score four VIP tickets to the Major League Soccer All-Star Game, plus round-trip airfare, hotel accommodations, rental car booking, and gift cards to cover gas and meals. You'll also receive Chicago Fire and Carvana swag, with a total estimated retail value of $5,000. Don't miss this opportunity to win big with Carvana.
Win $5,000 in value – Carvana 2026 Ultimate All-Star Soccer Experience Giveaway - Enter Now
Enter to win The Open Water Chicago Festival Flyaway Sweepstakes, an epic giveaway where you can score a Festival Rock Flight® prize package. This amazing prize includes 2 4-day General Admission tickets to Lollapalooza® at Grant Park in Chicago, IL, from July 30, 2026 to August 2, 2026. You'll also get round-trip air transportation for 2, a 5-night hotel stay, and a $500 pre-paid cash card for ground transportation. With a prize like this, you'll be rocking out in style, courtesy of Live Nation.
Win $7,200 in value – Open Water Chicago Festival Flyaway Sweepstakes - Enter Now
Enter the Farmers Chicago Cubs VIP Experience Sweepstakes for a chance to win an unforgettable trip to Chicago. Six grand prizes are up for grabs, each valued at $7,550. Winners will receive a trip for two to attend the Chicago Cubs game on August 15, 2026, including roundtrip airfare, 2 nights' hotel accommodations, a $250 prepaid card, suite tickets, and exclusive experiences like a Wrigley Field Press Box tour and Cubs Alumni Ambassador Meet & Greet. Plus, winners will get an autographed baseball and a $100 Cubs Store gift card. The total prize value is $45,300. Don't miss this opportunity to win a prize package and experience the ultimate Cubs game day with Farmers.
Enter the Farmers Chicago Cubs VIP Experience Sweepstakes for a chance to win an unforgettable trip to Chicago, Illinois. The prize package includes roundtrip air transportation for two, a 2-night hotel stay, a $250 prepaid card, and two suite tickets to the August 15, 2026 Chicago Cubs game. Winners will also get to experience the Wrigley Field Press Box, take pregame field photos, and meet a Cubs Alumni Ambassador. Additionally, they'll receive an autographed baseball and a $100 Cubs Store gift card. The approximate retail value of each grand prize is $7,550, with a total ARV of all prizes being $45,300. Don't miss this opportunity to win big - enter the Farmers Chicago Cubs VIP Experience Sweepstakes today for a free entry and a chance to take home an amazing prize.
Win $45,300 in value – Farmers Chicago Cubs VIP Experience Sweepstakes - Enter Now
Get ready to rock with AMI Entertainment's Riot Fest Sweepstakes. Enter to win an epic prize package, featuring two 3-Day Deluxe Passes to Riot Fest, held September 18-20, 2026, at Douglass Park in Chicago, Illinois, with a total approximate retail value of $1,919.96. To enter, download the AMI Play app and play any song from the Riot Fest Giveaway playlist on a participating AMI jukebox in Illinois, Indiana, Wisconsin, Michigan, Ohio, Missouri, or Iowa. Each song play equals one entry into the sweepstakes. Alternatively, complete the online entry form at for a free entry. Open to legal residents of the 50 United States or District of Columbia, 18 years or older, from June 25, 2026, to July 9, 2026. AMI Entertainment is a proud sponsor of Riot Fest, and we can't wait to see you there. Enter now for your chance to win with AMI Entertainment's Riot Fest Sweepstakes.
Win $1,919 in value – AMI Entertainment Riot Fest Sweepstakes - Enter Now
Enter to win the GoodReads (eBook) Chicago On Fire Book Giveaway and get ready for a thrilling ride. In "Chicago On Fire" by Ezz Abdel, a wave of calculated homicides pushes the city to the brink, prompting a joint task force of the FBI and the Chicago Police Department to take action. Led by FBI Special Agent Blake Sankey, the team must navigate a sinister conspiracy threatening to consume Chicago. With the body count rising, they must expose the truth before it's too late. Enter this free giveaway for a chance to win and dive into the gripping world of "Chicago On Fire".
Win $500 in value – GoodReads (eBook) Chicago On Fire Book Giveaway - Enter Now
Enter the Crate & Barrel The Bear Sweepstakes for a chance to win an exciting prize package. No purchase necessary to enter or win. The sweepstakes starts on 6/16/2026 and closes on 8/11/2026. To enter, fill out the online form or mail a 3x5 inch paper with your contact information to the address provided. One entry per person. The grand prize includes round-trip flights to Chicago, a 3-night stay, dinner, and tickets to a Chicago experience, $1,000 spending money, a $1,000 Crate & Barrel Gift Card, and more. Enter now for a free chance to win. Sponsored by Euromarket Designs, Inc. d/b/a Crate & Barrel, and Crate & Barrel Canada, Inc., the Crate & Barrel The Bear Sweepstakes is a giveaway you won't want to miss.
Win $6,800 in value – Crate & Barrel The Bear Sweepstakes - Enter Now
Enter the Chicago White Sox Ultimate Fan Sweepstakes, presented by Chicago White Sox, Ltd., for a chance to win exciting prizes. Employees of Chicago White Sox, Ltd., MLB Entities, and their immediate family members are not eligible. To enter, visit whitesox.com/sweepstakes and complete the online entry form during one of the six entry periods, which run from March 14, 2026, to August 30, 2026. Limit one entry per person/email address. Six prizes will be awarded, including tickets to Chicago White Sox games, VIP access, and more, with a total approximate retail value of $13,000. Enter now for your chance to win and become the ultimate Chicago White Sox fan, courtesy of Chicago White Sox, Ltd.
Win $13,000 in value – Chicago White Sox Ultimate Fan Sweepstakes - 6 Winners - Enter Now
