Chicago Sweepstakes
Found 23 total
Enter to win the QR Calgary (770 AM) Your Swing at an All-Star Experience in Chicago Giveaway.
This giveaway offers a trip for two to Chicago, including MLB All-Star Week tickets.
- One winner will receive the prize.
- The approximate retail value of the prize is $15,000 CAD.
- The giveaway ends on October 23, 2026.
Enter to win the WLS-AM King’s X House of Blues Chicago Ticket Giveaway.
This giveaway provides tickets to see King’s X live at the House of Blues in Chicago, valued at $100 USD. The giveaway ends on October 16, 2026.
Win $100 in value – WLS-AM King’s X House of Blues Chicago Ticket Giveaway - Enter Now
Enter to win the Just Another Year Chicago: Blackhawks Connor Bedard Jersey Giveaway.
Offers a single prize. - 1 Connor Bedard Chicago Blackhawks jersey (#98) with an approximate retail value of $150 USD. There will be one winner.
To enter on X, follow the account, like the post, and reply or retweet as directed; bonus actions earn extra entries.
Eligibility is not stated in the available post or rules. Ends October 16, 2026 at 11:59 PM EDT.
Win $150 in value – Just Another Year Chicago: Blackhawks Connor Bedard Jersey Giveaway - Enter Now
Enter to win the Alta Rehab at Fairmont Da Bears Giveaway.
One winner receives a Chicago Bears package worth $200: team flag, cap, beanie, gloves, tumbler, beer glasses, coasters, blanket and more.
To enter on Facebook, like the post and follow the page, share the post publicly, and comment your favorite Bears player while tagging a friend.
The winner will be announced Friday, October 16, 2026.
Win $200 in value – Alta Rehab at Fairmont Da Bears Giveaway - Enter Now
Enter to win the WOR Tickets To See Chicago Sweepstakes. IHeartMedia + Entertainment, Inc. Tickets To See Chicago Sweepstakes offers one winner the chance to receive two tickets to see Chicago at Flagstar at Westbury Music Fair on November 13, 2026. - 2 tickets to see Chicago at Flagstar at Westbury Music Fair on November 13, 2026 (ARV $120 USD). The sweepstakes will have one winner.
Win $120 in value – WOR Tickets To See Chicago Sweepstakes - Enter Now
Enter to win the Never Without Childcare Postpartum Services Giveaway.
The winner receives one featured service: a 1-hour postpartum massage, a 1-hour IV hydration session or 4 hours of date night childcare.
To enter on Facebook, follow Never Without Childcare on Instagram, Facebook and TikTok, repost and share the post, comment MOM and tag another mom.
Open to Chicago-area residents who gave birth within the last 6 months. Winners are announced October 16, 2026.
Win $350 in value – Never Without Childcare Postpartum Services Giveaway - Enter Now
Enter to win the Circa Sports Illinois Bet The Blitz Football Promotion - 7 Winners.
Circa Sports Illinois Bet The Blitz Football Promotion offers a total of seven prizes across two drawing dates and ends on Thursday, October 15, 2026. - Regular Prizes (6 Winners): A Las Vegas sports weekend consisting of a 2‑night stay (Wednesday and Thursday nights up to Week 17 of the NFL season) for the winner and a guest at Circa Resort & Casino, plus a VIP Football experience with two reserved pod spots at the Circa Sportsbook (ARV: $1,000.00 USD each). - Grand Prize (1 Winner): Two tickets to the New Orleans Saints vs. Chicago Bears game on Sunday, November 22 at Soldier Field in Chicago, IL (ARV: $1,000.00 USD).
The winner is picked at random.
Win $7,000 in value – Circa Sports Illinois Bet The Blitz Football Promotion - 7 Winners - Enter Now
Enter to win the Windy City Sports Cards Chicago Bears Rivalry Hoodie Giveaway - 3 Winners.
Three winners each receive a Chicago Bears Rivalry hoodie.
To enter on X, like and repost the post and follow @312SportsCards1.
Winners are announced October 15, 2026.
Enter to win the Chicago Blackhawks Bank on the Blackhawks Sweepstakes.
One winner receives four Chicago Blackhawks jerseys (ARV $750) and four tickets to the Blackhawks home game vs. the Seattle Kraken at the United Center on April 10, 2027 (ARV $1,100); total ARV $1,850. Transportation is not included.
To enter, fill out the entry form on the Bank on the Blackhawks page with your name, email, phone number and date of birth. Limit 1 entry per person. No purchase necessary.
Sponsored by Byline Bank. Open to US residents 18+ who live within 75 miles of the United Center in Chicago. The sweepstakes runs October 6, 2026 through March 30, 2027 at 11:59 PM CT; one winner is drawn at random and notified by email about one business day later.
Win $1,850 in value – Chicago Blackhawks Bank on the Blackhawks Sweepstakes - Enter Now
Enter to win the Takis® KATSEYE Concert Ticket Sweepstakes - 5 Winners.
Five winners (one per Concert Drawing) each receive a VIP concert ticket package with two tickets to the KATSEYE concert in Atlanta, New York, Chicago, Dallas or Los Angeles (ARV up to $800 each; tickets only, no travel).
To enter, submit the online entry form at takiskatseyegiveaway.com and pick one concert city drawing; get up to two extra entries by adding your Instagram and/or TikTok handle and following @takisusa (max 3 entries per person).
Open to legal residents of the 50 US and DC, 18+. Drawings close Oct 7, Oct 15, Oct 28, Nov 2 and Nov 12, 2026 at 11:59 PM ET.
Win $4,000 in value – Takis® KATSEYE Concert Ticket Sweepstakes - 5 Winners - Enter Now
