Chicago Sweepstakes
Found 21 total
Enter the Chicago and Styx Tour SiriusXM Sweepstakes for a chance to win an unforgettable prize package. One grand prize winner will receive round-trip coach air transportation for two to Los Angeles, CA, a two-night hotel accommodation, and two VIP tickets to see Chicago and Styx on the Windy City Tour. The VIP packages include exclusive merchandise, backstage access, and premium tickets. The approximate retail value of the prize is $3,500. Sweepstakes ends at 11:00 PM ET on July 24, 2026. Enter to win this amazing giveaway and get ready to rock with Chicago and Styx.
Win $3,500 in value – Chicago and Styx Tour SiriusXM Sweepstakes - Enter Now
Enter the Motorola Chicago Festival x razr Sweepstakes for a chance to win an exciting Prize Package. The sweepstakes is open to legal residents of the 50 United States and DC, 18 years or older. To enter, register via the designated link on Motorola's Instagram (@motorolaus), marketing communications, or website (https://www.motorola.com) from July 20, 2026, at 10:00 AM CT to July 27, 2026, at 11:59 PM CT. One entry per person is allowed. Two winners will be randomly selected to receive a Prize Package, including two Saturday VIP tickets to Lollapalooza festival (ARV $370) and a 2026 motorola razr ultra (ARV $1,499). Motorola Mobility LLC is the sponsor of this sweepstakes, and by entering, you agree to the official rules. Winners will be notified via email on or about July 29, 2026. Enter now for a free chance to win with Motorola.
Win $4,478 in value – Motorola Chicago Festival x razr Sweepstakes - 2 Winners - Enter Now
Enter to win the Fever Basketball, LLC The Ultimate Road Trip Sweepstakes 2026 for a chance to score an unforgettable prize package. The lucky winner will receive two courtside tickets to the Indiana Fever vs. Chicago Sky game, a team store gift certificate, a Visa gift card, an Albanese prize pack, and a tour of the Albanese Candy Factory. Plus, get roundtrip transportation to the factory and the game. The total prize value is $3,789.88. Free entry is available until July 29th, 2026, at 4:00 PM Indianapolis time. Don't miss this opportunity to win big with Fever Basketball, LLC.
Win $3,789 in value – Fever Basketball, LLC The Ultimate Road Trip Sweepstakes 2026 - Enter Now
Enter the Flyyeg Night At The Races Contest for a chance to win an exciting travel prize. One lucky winner will receive a flight certificate redeemable at Paull Travel for two non-stop economy class round-trip flights to a destination of their choice, including Chicago, Houston, San Francisco, Las Vegas, Cancun, Puerto Vallarta, Reykjavik, or Montego Bay, with a maximum value of $4,500. Don't miss out - enter to win this amazing prize before the contest ends on September 14, 2026.
Win $4,500 in value – Flyyeg Night At The Races Contest - 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 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 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
