Chicago Sweepstakes
Found 27 total
Get ready to score big with the Chicago Bears Rome Odunze Signed Brush Giveaway. Enter to win a unique Rome Odunze signed brush, valued at $100, courtesy of the Chicago Bears. This exciting sweepstakes offers a free entry for a chance to take home the prized brush. Don't miss out - enter now and take a shot at winning this exclusive prize, brought to you by the Chicago Bears.
Win $100 in value – Chicago Bears Rome Odunze Signed Brush Giveaway - 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 Chicago & Styx on The Windy Cities Tour Sweepstakes, presented by iHeartMedia + Entertainment, Inc, for a chance to win an exciting trip for two to see Chicago & Styx live in concert. The grand prize package, valued at $3,000, includes round-trip air transportation, two nights of hotel accommodations, two concert tickets, a $200 gift card for ground transportation, a signed Styx guitar, and an on-stage moment with Chicago during the encore. To enter, visit any participating station website or the iHeartRadio app and complete the entry form between May 18, 2026, and May 24, 2026. Earn bonus entries by listening to Chicago or Styx on the iHeartRadio app. Open to legal residents of the 50 United States and the District of Columbia, 18 years or older. One winner will be randomly selected on or about May 26, 2026. Don't miss this opportunity to win, courtesy of iHeartMedia + Entertainment, Inc.
Win $3,000 in value – Chicago & Styx on The Windy Cities Tour iHeartmedia Sweepstakes - Enter Now
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
Get ready to score with the Chicago History Jersey Giveaway. Enter to win a brand new Chicago Bears jersey, valued at $130, courtesy of our exciting sweepstakes. Join the giveaway for a free entry and take a chance to win this incredible prize. Enter now with Company to win big. Company brings you the Chicago History Jersey Giveaway.
Win $130 in value – Chicago History Jersey Giveaway - Enter Now
Enter the Welch's Fusions Chicago Festival Sweepstakes for a chance to win an exciting prize package. The grand prize includes two 4-day VIP tickets to Lollapalooza in Chicago, round-trip air transportation, a 5-night hotel stay, and more, valued at approximately $8,505. To enter, visit the promotion entry page and complete the entry form. You can also earn up to six bonus entries by subscribing to email offers, watching a short video, or answering a survey question. The sweepstakes is open to legal residents of the 50 United States and the District of Columbia, who are at least 18 years old. No purchase necessary, and entries will be accepted until June 30, 2026. PIM Brands, Inc., the Sponsor, and Live Nation Worldwide, Inc., the Administrator, are not responsible for lost or stolen prizes. Enter now for your chance to win, courtesy of Welch's Fusions and Live Nation.
Win $8,505 in value – Welch's Fusions Chicago Festival Sweepstakes - Enter Now
Enter to win The Chicago Cubs Grand Slam Getaway Fueled By Omaha Steaks Sweepstakes for a chance to score an unforgettable prize package. Two Grand Prizes are up for grabs, each valued at $4,900. Winners will receive a trip for two to Chicago, Illinois, including round-trip airfare, two-night hotel accommodations, and tickets to a Chicago Cubs home game on July 4, 2026, at Wrigley Field. They'll also get Chicago Cubs jerseys, a $100 Uber Gift Card, and a $100 pre-paid bank gift card. Plus, enjoy Omaha Steaks for a Year with four shipments of the Triple Crown Combo. The total prize value is $9,800. Don't miss your chance to win - enter by Sunday, June 7, 2026, at 11:59 PM CST.
Win $9,800 in value – Chicago Cubs Grand Slam Getaway Fueled By Omaha Steaks Sweepstakes - Enter Now
Enter the Lagunitas Brewing Salt Shed Sweepstakes for a chance to win a premium experience. Each winner will receive a prize package with an approximate retail value of $1,750, including two premium concert tickets at Salt Shed in Chicago, a $250 Lagunitas merchandise gift card, and a $1,000 gift card for transportation, lodging, and incidentals. Enter to win this exciting sweepstakes and get ready for an unforgettable experience with Lagunitas Brewing.
Win $5,250 in value – Lagunitas Brewing Salt Shed Sweepstakes - Enter Now
Enter to win exciting prizes in the Mountain Dew Rock The Mountain Sweepstakes, open to legal residents of IA, IL, IN, KS, MN, MO, NE, SD, and WI, 18+ (19 in NE). The promotion period runs from April 4, 2026, to October 4, 2026. Play the instant win game by scanning the code on participating retailer signage or visiting mountaindewpromos.com/rockthemountain. Limit one play per person, per email, per household per day. Win instant prizes like Mountain Dew Can Coolers, Speakers, Totes, Spotify subscriptions, and gift cards, with a total of 1,200 instant win prizes available. Additionally, be entered into the Grand Prize Drawing for a trip for two to a concert at the United Center in Chicago, IL, with five Grand Prizes available. The total ARV of all prizes is up to $64,066. Pepsi-Cola Company, the Sponsor, reserves the right to modify the promotion. Enter for free and follow the on-screen instructions to play and claim your prize if you win.
Win $63,000 in value – Mountain Dew Rock The Mountain Instant Win Game Sweepstakes - Enter Now
Get ready to escape to Chicago with the Chicago City Escape EMC2 Hotel Autograpgh Collection Sweepstakes. Enter to win a grand prize valued at $1550, featuring a 3-night stay at the EMC2 Hotel, Autograph Collection, and a $350 resort credit. Don't miss your chance to win this incredible prize, courtesy of Ecommerce Advisors. The sweepstakes ends on 6/7/2026 at 11:59 pm EDT, so submit your free entry now and take a shot at this amazing getaway with Ecommerce Advisors.
Win $1,550 in value – Chicago City Escape EMC2 Hotel Autograpgh Collection Sweepstakes - Enter Now
