Chicago Sweepstakes
Found 26 total
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
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
Enter the Lollapalooza 2026 SiriusXM Sweepstakes for a chance to win an epic prize package. One Grand Prize winner will receive a 5-night trip to Chicago, IL, including round-trip air transportation for two, hotel accommodations, and two VIP 4-day tickets to the 2026 Lollapalooza Festival. The prize package is valued at approximately $3,500. To be eligible, participants must enter by 11:59 pm ET on June 29, 2026. Don't miss this opportunity to win a free trip and experience the ultimate music festival with SiriusXM.
Win $3,500 in value – Lollapalooza 2026 SiriusXM Sweepstakes - Enter Now
Enter the Corona MLB at Field of Dreams Sweepstakes for a chance to win a pair of tickets to the 2026 MLB at Field of Dreams game, hotel accommodations, and $250 towards travel. The sweepstakes is open to legal U.S. residents of IA, IL, MN, MO, NE, SD, and WI, 21 years or older. No purchase necessary. To enter, scan the QR code on display at participating Corona retailers and text CORONA to 20102, or mail a 3x5 paper with your contact information to the provided address. Three grand prizes are available, each with an approximate retail value of $860. The sweepstakes begins on May 11, 2026, and ends on July 26, 2026. Crown Imports LLC, the sponsor, is not responsible for lost or damaged prizes. By participating, you agree to the official rules and release the Released Parties from liability. Relax responsibly with Corona Extra Beer, imported by Crown Imports LLC, Chicago, IL.
Win $2,580 in value – Corona MLB at Field of Dreams Sweepstakes - Enter Now
