Chicago Sweepstakes
Found 21 total
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 Manhattan Vintage Show The Goods Giveaway.
Prize package includes two VIP All-Access Passes to Manhattan Vintage's first Chicago show, shopping credits at Hachi Archive ($250), molimo fine jewelry ($250), Well Worn Art ($200), Monique Gatillon ($100), $50 food/beverage credit, and a 1930s Chicago-related bonus (listed total about $1,100).
To enter: follow the steps on the Manhattan Vintage Show Facebook post.
Local Chicago show promo. Ends October 12, 2026 at 11:59 PM CDT.
Win $1,100 in value – Manhattan Vintage Show The Goods Giveaway - Enter Now
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
Enter to win the Hubbard Radio Chicago Harry Styles at Soldier Field Giveaway. Hubbard Radio Chicago, LLC's Harry Styles at Soldier Field Giveaway offers a chance to win tickets to see Harry Styles live at Soldier Field in Chicago, Illinois, on May 28, 2027. - 2 tickets to Harry Styles at Soldier Field, Chicago, IL — May 28, 2027. There will be one winner. The approximate retail value per winner is $400 USD, and the total approximate retail value is $400 USD. The giveaway ends on October 23, 2026.
Win $400 in value – Hubbard Radio Chicago Harry Styles at Soldier Field Giveaway - Enter Now
Enter to win the Fanta Build Your Alebrije Sweepstakes and Instant Win Game - 101 Winners.
Grand Prize (1): a 4-day/3-night trip for two to the Day of the Dead Ball in Chicago in November 2027, with round-trip airfare, three nights' hotel, two event tickets, a guided Día de Muertos exhibition tour, a $250 transportation gift card and a $500 check (ARV $4,600).
Instant win Game Prizes (100): a Day of the Dead altar prize kit (ARV $79.61 each).
How to win: visit the Fanta Alebrije promotion website (or scan the QR code on specially marked materials), create an Alebrije, then log in or create a free Coca-Cola account to receive one sweepstakes entry (limit one entry per day). Complete a five-question survey for your game play (limit one game play for the entire promotion); a win or non-win message appears instantly. The Grand Prize winner is drawn on or about November 9, 2026. The promotion runs October 1, 2026 (10:00 AM ET) through November 6, 2026, at 11:59 PM ET. Open to 21+ residents of the 50 U.S. and D.C. No purchase necessary.
Enter to win the Goodreads (eBook) Dina Gets Lucky Book Giveaway. Invites readers to enter for a chance to win the eBook “Dina Gets Lucky” by Uzma Jalaluddin. Toronto attorney Dina Haq is looking forward to her influencer sister’s lavish South Asian wedding, but she does not want to overshadow the event of the season by revealing her own carefully guarded secret. Her marriage has gone bust, and she must also keep her odious ex from speaking out. Complications arise when she discovers that the groom’s best man is Luqman “Lucky” Latif, a law‑school crush who ghosted her six years ago. Lucky abandoned his lawyerly ambitions to help his struggling family in Chicago, rebuilt his life with a successful contracting business, and believes he has moved on from past hurts. When he sees Dina again—the woman who rejected him and married his best friend—he doubts whether his heart can survive another encounter. As the wedding festivities unfold, Dina and Lucky rediscover their connection and begin to unravel the role her manipulative ex‑husband played in their almost‑love story. The past isn’t quite what they thought, but they wonder if it is too late to imagine a new future together.
Win $400 in value – Goodreads (eBook) Dina Gets Lucky Book Giveaway - Enter Now
Goodreads (eBook) Jan Frost Book Giveaway. Enter the Goodreads giveaway for Jan Frost by Serena Pier. She is his online fantasy, and he is her most devoted subscriber. On a snowy Chicago night, the spark between them turns a parasocial obsession into a dangerous connection. What should be a holiday fling instead becomes something neither of them can walk away from, because once Jan Frost decides something is his, he does not let it go. This filthy yet surprisingly sentimental age‑gap romance follows Jan Frost as a wealthy reformed criminal, cold and untouchable as winter itself, meets the one woman hot enough to melt him.
Win $500 in value – Goodreads (eBook) Jan Frost Book Giveaway - Enter Now
