Chicago Sweepstakes
Found 23 total
Get ready to win big with the DoubleTree by Hilton Chicago-Alsip Family Fun Giveaway! Enter to win an exciting prize package valued at over $500, featuring a one-night double-bed stay at DoubleTree by Hilton Chicago-Alsip on July 31, 2026. The fun continues with breakfast for four at Spotlight Lounge & Restaurant, four tickets to the thrilling Windy City Thunderbolts game on July 31st, and four passes to the interactive Oak Lawn Children's Museum. Don't miss your chance to win this amazing family getaway - enter the DoubleTree by Hilton Chicago-Alsip Family Fun Giveaway before the deadline on July 23, 2026, at 11:59 pm.
Win $500 in value – DoubleTree by Hilton Chicago-Alsip Family Fun Giveaway - Enter Now
Enter the Dawn McKenna Group Gift Card Giveaway for a chance to win a $250 gift card to Dimmi, perfect for your next Italian dinner in Chicago's Lincoln Park. The lucky winner will be announced on Friday, July 17, so enter to win this amazing prize today with a free entry in our exciting sweepstakes and giveaway.
Win $250 in value – Dawn McKenna Group Gift Card Giveaway - Enter Now
Enter the C4 Energy x Chicago Fire Tickets Sweepstakes for a chance to win an exciting prize package. Score big with four tickets to the Chicago Fire FC® game on September 14, 2026, plus four custom Chicago Fire FC® jerseys and a Visa® gift card. The total prize value is $1,060.00 USD. Don't miss out - enter to win this amazing giveaway before it ends on August 31, 2026, at 11:59 PM CT.
Win $1,060 in value – C4 Energy x Chicago Fire Tickets Sweepstakes - Enter Now
Enter the Margaritaville at Sea + Zac Brown Band National Contest for a chance to win exciting prizes. Up to 27 Market Winners will receive a pair of tickets to see Zac Brown Band live in various cities, including Pittsburgh, New York, Philadelphia, Kansas City, Miami, Greenville, Greensboro, Denver, and Chicago, with ticket values ranging from approximately $339.04 to $694.18. One Grand Prize Winner will receive a prize valued at up to $3,000.00. The contest is open through approximately 12:59 am (ET) on Monday, November 2, 2026. Don't miss this opportunity to win a free prize and experience the thrill of a live concert, courtesy of Margaritaville at Sea. Enter to win now and take a chance at an unforgettable experience with Margaritaville at Sea.
Win $3,000 in value – Margaritaville at Sea + Zac Brown Band National Contest - Enter Now
Enter the BeatBox Beverages Chicago Festival Sweepstakes for a chance to win a prize package worth $8,996.00, including two 4-day VIP tickets to Lollapalooza and a $2,000 travel credit. Sweepstakes runs from July 1, 2026, to July 18, 2026. Enter online at https://gleam.io/Qhyue/beatbox-beverages-chicago-festival-2026-sweepstakes or by scanning the QR code on promotional materials. Limit 16 additional entries per person per day. Winner will be selected in a random drawing on July 19, 2026. BeatBox Beverages is giving away this amazing prize, so don't miss your chance to win. Enter now and you could be rocking out at Lollapalooza with a friend, courtesy of BeatBox Beverages.
Win $8,996 in value – BeatBox Beverages Chicago Festival Sweepstakes - Enter Now
Enter the Southwest Airlines Runway to Wrigley Sweepstakes for a chance to win an unforgettable prize package. The winner and their guest will receive a thrilling experience, including two tickets to a 2026 Chicago Cubs home game, a Wrigley Field Scoreboard viewing experience, 50,000 Southwest Airlines Rapid Rewards bonus points, a one-night hotel stay, and exclusive autographed memorabilia. The approximate retail value of the prize is $3,052.41. Don't miss this opportunity to win big with Southwest Airlines.
Win $3,052 in value – Southwest Airlines Runway to Wrigley 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 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
