Chicago Sweepstakes
Found 18 total
Enter the Chicago’s About Get Loud Giveaway from Insta360 for a chance to win two cutting‑edge cameras – a Luna Ultra (≈$300) and an Insta360 Ace Pro (≈$199) – a total prize value of $499. Two winners will be randomly selected, one per prize, and the contest ends August 10, 2026. Open to U.S. residents 18+, entry requires following @insta360_usa, liking, reposting, commenting with a festival moment and tagging friends, plus a bonus entry using #FestivalWithInsta360. No purchase necessary.
Win $499 in value – Insta360 Chicago’s About Get Loud Giveaway - 2 Winners - Enter Now
Enter the Xfinity Rewards Zac Brown Band live in Chicago Sweepstakes for a chance to win an unforgettable experience. The prize package includes VIP tickets to a "Love & Fear Tour" show at Allstate Arena, three-day hotel accommodations, round-trip airfare, and VIP perks like priority check-in and a dedicated "fast lane" for merch shopping. Additionally, you'll receive a $600 prepaid gift card to cover extra expenses. The total prize value is approximately $3,350. Don't miss out - enter to win this amazing prize before the contest ends on August 16, 2026, at 11:59:59 p.m. ET.
Win $3,350 in value – Xfinity Rewards Zac Brown Band live in Chicago Sweepstakes - Enter Now
Enter the Bobbles & Lace Chicago Gift Card Giveaway for a chance to win a $1,000 shopping spree and personal styling experience! This exciting sweepstakes is open until August 2 at 7:00 PM, allowing you to score the ultimate Bobbles & Lace Chicago prize. Enter to win this amazing giveaway and get ready to elevate your style with Bobbles & Lace Chicago.
Win $1,000 in value – Bobbles & Lace Chicago $1000 Giveaway - 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
