Chicago Sweepstakes
Found 20 total
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 GARAGE Dream Trip Giveaway.
One winner and a guest receive a VIP trip to Washington DC, Miami, New York, Chicago or Los Angeles: round-trip economy airfare, a 2-night hotel stay, up to $500 Uber credit, up to $500 meal credit per person, a $500 GARAGE gift card per person and VIP gifting (ARV $4,500).
To enter, join (or sign in to) the free GARAGE loyalty program and submit your loyalty email on the contest landing page. Earn 1 bonus entry for each friend you refer who joins the loyalty program. You can also enter by mail (see the rules).
No purchase necessary. Open to legal residents of Canada and the US, 21+. The trip giveaway ends October 9, 2026 at 11:59 PM ET; the drawing is October 13.
Win $4,500 in value – GARAGE Dream Trip Giveaway - Enter Now
Enter to win the Chicago Bears Battle of the Border Sweepstakes.
One winner and a guest receive 2 tickets to the Bears at Packers game at Lambeau Field on October 11, 2026 ($412) with a one-night hotel stay in Appleton, WI on October 10 ($576.35), plus 2 tickets to the Bears vs. Packers home game at Soldier Field on December 25, 2026 ($454), a parking pass ($55), $50 in Bears Balance and a Chicago Bears autographed item ($150); total ARV $1,697.35.
To enter, complete the entry form on the Chicago Bears Battle of the Border Sweepstakes page (powered by Verizon). Limit 1 entry per person. No purchase necessary.
Open to US residents 18+, excluding Rhode Island. The NFL sweepstakes runs October 1, 2026 at 10:00 AM CT through October 8, 2026 at 11:59 PM CT; one winner is drawn at random on or about October 9.
Win $1,697 in value – Chicago Bears Battle of the Border 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
Goodreads (eBook) My Darling Girls Book Giveaway – Enter the Goodreads giveaway for My Darling Girls by Marina Scott. In 1904 Chicago, secrets cling as thickly as the soot on every windowsill, and Jo earns her living by photographing the dead. Her work is quiet and cloistered, allowing her to hide from a past that haunts her with grief over her husband’s mysterious death, a spiraling addiction, and the guilt she carries for the things she has done to survive. When a notorious crime family hires Jo to make a final portrait of their daughter Millie, it stirs up a spirit that refuses to rest. In opium‑fueled dreams, Millie lures Jo into a realm called “the courtyard,” where the dead burn to tell their half‑finished stories. As Jo investigates Millie’s murder, she forms a fragile bond with her sister Grace, who is desperate for an escape of her own. Amid the whispers of the dead, Jo must confront a truth if she is to free them all from the shadows of the past.
Win $500 in value – Goodreads (eBook) My Darling Girls Book Giveaway - Enter Now
Gorilla Energy Drink VIP Fight Experience Sweepstakes ends on 08 October 2026 at 11:59 PM CDT. The winner(s) will receive the following prizes:
- One winner will receive a Full VIP PFL Chicago Experience plus Exclusive MMA gloves (approximate retail value $1,600).
- One winner will receive a $500 Visa Gift Card and a free Gorilla Energy three‑month supply (approximate retail value $500).
- One winner will receive a free Gorilla Energy three‑month supply (approximate retail value $100).
Win $2,200 in value – Gorilla Energy Drink VIP Fight Experience Sweepstakes - Enter Now
