Chicago Sweepstakes
Found 28 total
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 Skydeck Chicago and Hotel Zachary A Day Off In Chicago Sweepstakes for a chance to win an unforgettable Chicago experience. One lucky winner will receive a prize package valued at $1,860, including a one-night stay at Hotel Zachary, $100 food and beverage credit, two Chicago Cubs game tickets, expedited Skydeck Chicago tickets, and a private Art Institute of Chicago tour. Don't miss out - enter to win this amazing giveaway before it ends on June 15, 2026, at 11:59 p.m. CT.
Win $1,860 in value – Skydeck Chicago and Hotel Zachary A Day Off In Chicago Sweepstakes - Enter Now
Enter to win the GoodReads (Print) When No One Else Will Book Giveaway for a chance to receive a free copy of Amanda Skenandore's novel. This gripping story follows Mimi Lukas as she navigates a private battle in her Chicago neighborhood amidst the outbreak of war in Europe. As Mimi finds her footing in a women's clinic, she must confront the moral implications of her work and decide how much she's willing to risk. With its thought-provoking themes and relatable characters, When No One Else Will is a must-read. Enter the GoodReads giveaway now for your opportunity to win this captivating book, courtesy of GoodReads.
Win $450 in value – GoodReads (Print) When No One Else Will Book Giveaway - 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 Xfinity Rewards WNBA Stars Sweepstakes for a chance to win an unforgettable prize package. The winner will receive two tickets to the WNBA All-Star Game on July 25, 2026, at the United Center in Chicago, IL, plus a three-day, two-night hotel stay and round-trip airfare for two. A $600 prepaid gift card is also included to cover incidental expenses. The total prize value is approximately $4,800. Don't miss out - enter to win this amazing prize by June 18, 2026, at 11:59 p.m. ET.
Win $4,800 in value – Xfinity Rewards WNBA Stars 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
Enter the Mike’s Dirty Lemonade The All-American Rejects Flyaway Concert Giveaway for a chance to win an unforgettable experience. To participate, simply access the official Mike's Hard Lemonade Instagram or TikTok page, follow the account if you don't already, and click on the designated button in the Giveaway post to access the entry form. Complete and submit the form with all required information, including your first name, last name, email address, phone number, state of residence, and your "dirty secret." The Giveaway begins on May 16, 2026, and ends on June 15, 2026. One lucky winner will receive tickets for themselves and up to two verified guests to attend The All-American Rejects concert in Chicago, Illinois, including a meet and greet opportunity, round-trip coach air travel, hotel accommodations, and a $500 check. Don't miss this amazing opportunity to win a prize valued at up to $4,600. Enter the Mike’s Dirty Lemonade The All-American Rejects Flyaway Concert Giveaway today and get ready to rock out with Mark Anthony Brands Inc. Quick tip: Enter once a day through either Instagram or TikTok (the form is the same). You must submit a new “dirty secret” each time.
Enter the Do312 Chicago Festival Flyaway Sweepstakes for a chance to win a prize package valued at $3,130.00, including two 4-day VIP tickets to the 2026 Lollapalooza Music Festival in Chicago. Open to US residents 21+, the sweepstakes runs from April 13, 2026, to June 30, 2026. To enter, visit https://dostuffmedia.com/giveaways/chicago-flyaway-2026 or email [email protected]. One entry per person, with a limit of one entry during the promotion period. DoStuff Media LLC sponsors this sweepstakes, and all potential winners are subject to verification. Don't miss this opportunity to win a fantastic prize - enter the Do312 Chicago Festival Flyaway Sweepstakes today, courtesy of DoStuff Media.
Win $5,300 in value – Do312 Chicago Festival Flyaway Sweepstakes - Enter Now
