Chicago Sweepstakes
Found 18 total
Enter to win The Shops at North Bridge Cozy Essentials Giveaway.
One winner gets cozy essentials: an $80 Mugsy gift card plus a Kate Spade Sip and Style Sudoku Set, a Stanley Quencher H2.0 FlowState 40-ounce tumbler and an UGG Everett faux fur throw from Nordstrom Chicago.
Open only to legal US residents residing in Illinois, 18 or older; the winner must pick up the prize at The Shops at North Bridge in Chicago. Ends October 26, 2026 at 11:59 PM CDT.
To enter, follow @theshopsatnorthbridge and @mugsy on Instagram, like the post and tag a friend in the comments (each tag is an additional entry).
Win $273 in value – The Shops at North Bridge Cozy Essentials Giveaway - Enter Now
Enter to win the Tricoci Salon and Spa Cupitol Coffee Spa Day Giveaway.
One winner gets Tricoci seasonal coffee-infused spa treatments (a classic manicure and pedicure and a massage) plus a $100 Cupitol gift card (about $330; tricoci.com lists the classic manicure at $40, classic pedicure at $60 and a 50-minute seasonal massage at $130).
Open to people 18 or older in the Chicago area of Illinois. Ends October 26, 2026 at 11:59 PM CDT.
To enter, follow Tricoci Salon & Spa and Cupitol, like the giveaway post and comment with your coffee order. The winner is contacted by DM from the official Tricoci account after the giveaway closes on October 26, 2026.
Win $330 in value – Tricoci Salon and Spa Cupitol Coffee Spa Day Giveaway - Enter Now
Enter to win the Crate and Barrel Bears Game Day Sweepstakes.
One winner gets 2 tickets to the Chicago Bears vs. Detroit Lions game at Soldier Field on January 3, 2027 and a $500 Crate and Barrel gift card.
Open to US residents 18 or older, excluding Rhode Island. Ends December 25, 2026 at 11:59 PM CST.
To enter, submit your name, email, age and phone number on the Crate and Barrel Bears Game Day sweepstakes page. One entry per person. The winner is drawn on or about December 26, 2026.
Win $2,500 in value – Crate and Barrel Bears Game Day Sweepstakes - Enter Now
Enter to win the Cambio Tequila Chicago Cubs 2027 Ticket Giveaway.
One winner gets two tickets to one eligible Chicago Cubs regular-season home game at Wrigley Field during the 2027 season (winner may request a preferred game, subject to availability; travel, parking and meals not included).
Open to legal US residents 21 and older. Runs September 16 through November 20, 2026 at 11:59 PM CST.
To enter, visit cambiotequila.com/cubs, enter your email, confirm you are 21+ and submit the form; limit one entry per person. The winner will be selected at random after the sweepstakes ends and contacted by email.
Win $500 in value – Cambio Tequila Chicago Cubs 2027 Ticket Giveaway - Enter Now
Enter to win the Sherwood Hockey 2026 Signature Series Mini Stick Contest - 101 Winners.
100 winners each get a golden mini stick autographed by Connor Bedard or Quinton Byfield ($350 USD each); golden-stick winners who confirm by December 31, 2026 go into a drawing for a trip for two to Chicago to meet Connor Bedard ($5000 USD). Total about $40000 USD.
Open to residents of the US, DC and Canada who are of the age of majority. Runs October 16, 2026 through May 1, 2027 or until all winning devices are found.
To enter, find a golden mini stick or ticket in a specially marked Sherwood Signature Series mystery mini-stick pack, or request a free virtual envelope at sherwoodhockey.com/collections/AMOE with a 100-word essay, then redeem on the Sherwood winner page. The trip winner will be drawn January 22, 2027.
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 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 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.
