Chicago Sweepstakes
Found 29 total
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
Get ready to rock with the PEPPERMAYO Summer Giveaway. Enter to win an epic Lollapalooza Chicago experience, including 4 tickets and $500 to cover your weekend fun. The prize package is valued at $1240, with travel costs not included. Don't miss your chance to win and share the excitement with your three best friends. A winner will be announced on Monday, so be sure to enter the PEPPERMAYO Summer Giveaway for a free entry to this amazing sweepstakes.
Win $1,240 in value – PEPPERMAYO Summer Giveaway - Enter Now
Glasgow Airport's USA Trip Giveaway is live. Win return flights for two to the United States, choosing from Chicago, Los Angeles, Newark/New York, San Francisco, or Orlando. One winner will be selected. Enter by commenting with your preferred city and following Glasgow Airport. Competition ends June 26, 2026. Winner will be contacted via this account. No payment details will be requested to claim the prize.
Win $1,000 in value – Glasgow Airport USA Trip Giveaway - 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 Liquid I.V. Chicago VIP Festival Sweepstakes for a chance to win a grand prize valued at $8,500. The Liquid I.V. Chicago VIP Festival Sweepstakes, sponsored by The LIV Group, Inc., dba Liquid I.V., offers a Festival Rock Flight package, including 4-day VIP tickets to Lollapalooza in Chicago, round-trip air transportation, a 5-night hotel stay, and a $500 pre-paid cash card. To enter, visit the promotion entry page and complete the entry form between May 27, 2026, and June 30, 2026. You can submit one entry per day, with a maximum of 38 entries, including up to three bonus entries for subscribing to receive email offers from Liquid I.V. One grand prize winner will be randomly selected on or around July 1, 2026. Enter now for a free chance to win with Liquid I.V.
Win $8,500 in value – Liquid I.V. Chicago VIP Festival Sweepstakes - Enter Now
The Grand Prize winner will receive a 3-day/2-night trip for two to AT&T WNBA All-Star Game 2026 in Chicago, IL between 7/24/26 and 7/26/26 consisting of round-trip coach air transportation from major airport nearest to winner’s residence in the U.S., standard occupancy hotel accommodations, and two tickets to the following events: AT&T WNBA All-Star Game 2026 on 7/25/26, Friday Night 3-Point Contest and Skills Competition. ARV of the Grand Prize package not to exceed $5,000.
How to Play: Vote for your WNBA All-Stars. Tap the cards to select up to 10 players. Login with your free WNBA ID to submit your ballot and re-populate your selections each day. *Vote each day until Saturday, June 27.
Win $15,000 in value – WNBA 2026 All-Star Voting Sweepstakes - Enter Now
Enter to win the Peet’s Coffee Chief Playlist Officer Contest for a chance to score an epic grand prize package valued at up to $6,800. This amazing sweepstakes giveaway includes a 4-night trip to Chicago, IL, with roundtrip airfare, hotel stay, and access to a music festival and exclusive media event. The winner and their guest will also receive VIP entry passes, a merchandise pack, and a $600 gift card. Don't miss out on this incredible opportunity to win big with Peet’s Coffee. The grand prize award is subject to certain terms and conditions, and travel dates are scheduled for 7/30/2026 – 8/3/2026. Enter now for your free chance to win with Peet’s Coffee.
Win $6,800 in value – Peet’s Coffee Chief Playlist Officer Contest - Enter Now
Get ready to win with the Giuliana Prosecco Windy City Smokeout Giveaway. Enter to win two 4-Day GA passes to Windy City Smokeout in Chicago, featuring live music, iconic barbecue, and plenty of Giuliana Prosecco. For a free entry, simply follow @giulianaprosecco, like this post, and comment "PROSECCO" below. Courtesy of Giuliana Prosecco, this sweepstakes offers an unforgettable weekend experience.
Win $599 in value – Giuliana Prosecco Windy City Smokeout Giveaway - Enter Now
