Chicago Sweepstakes
Found 19 total
Enter to win the 947WLS Florida Vacation Contest.
One winner and a guest receive a VISIT FLORIDA Orlando vacation: round-trip coach airfare to Orlando International Airport, a three-night stay at Caribe Royale Orlando, two Gatorland tickets, an ICON Park experience with The Orlando Eye, and two admissions each to SEA LIFE Orlando Aquarium, Madame Tussauds Orlando and Museum of Illusions Orlando (listed value $2500).
To enter, listen to 94.7 WLS on Fridays in October for the VISIT FLORIDA Floridays Song of the Day, then be caller nine at 312-922-9470.
For 94.7 WLS (Chicago) listeners; see the station contest rules. Runs Fridays through October 30, 2026.
Win $2,500 in value – 947WLS Florida Vacation Contest - Enter Now
Enter to win the Legit Street Cars Dodge Challenger Scat Pack Giveaway.
One winner receives a modified 2015 Dodge Challenger Scat Pack (ARV $35000), $5000 cash, and one-way economy airfare to Chicago for the winner and a guest plus one night of hotel if picking the car up in person ($1000). Total ARV $41000.
Open to legal residents of the 48 contiguous US states and DC who have reached the age of majority. Ends October 25, 2026 at 11:59 PM EDT.
Entries are earned with purchases in the Legit Street Cars online store (one entry per $1 spent). The free method of entry is by Postal Mail. See the AMOE in the official rules.
Win $41,000 in value – Legit Street Cars Dodge Challenger Scat Pack Giveaway - Enter Now
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 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 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
