Chicago Sweepstakes
Found 17 total
Enter to win the Chicago Bears Dr Pepper Ultimate Gameday Experience Sweepstakes.
One winner gets four tickets to the Bears vs Lions game on January 3, 2027 at Soldier Field, four pre-game sideline passes, $200 in Soldier Field concessions balance, one parking pass, one Chicago Bears autographed item, a 15-minute alumni meet and greet, a $500 Chicago Bears Pro Shop gift card and four knit hats; ARV $8688.
Open to contiguous US residents 18+ except Florida, New York and Rhode Island. Ends December 4, 2026 at 11:59 PM CST.
To enter, complete the online entry form at chicagobears.com/sweepstakes/drpepper with your name, date of birth, email, state and phone number; limit one entry per person. The winner is drawn on or about December 7, 2026.
Win $8,688 in value – Chicago Bears Dr Pepper Ultimate Gameday Experience Sweepstakes - Enter Now
Enter to win the Chicago Blackhawks BMO Ultimate Fan Sweepstakes - 41 Winners.
Forty-one winners (one per 2026-27 Blackhawks home game at the United Center) each get four 100-level tickets to a home game plus an autographed replica jersey (tickets ARV $560-$1061.76; jersey ARV $500).
Open to entrants 18+ (or age of majority) who are legal US residents living within 75 miles of Chicago city limits. Ends April 10, 2027 at 11:59 PM CST.
Enter once online at the BMO Ultimate Fan entry form during the promotion period.
Win $1,562 in value – Chicago Blackhawks BMO Ultimate Fan Sweepstakes - 41 Winners - Enter Now
Enter to win the Chicago Blackhawks Circa Win You Win Sweepstakes.
After each Blackhawks win, 101 winners are drawn: one Grand Prize winner gets a Circa Resort Las Vegas trip package including a two-night stay, $500 Stadium Swim credit, a Blackhawks Centennial jersey, and a round-trip flight credit (ARV $2000), and 100 winners each get a $100 Circa betting credit.
Open to entrants 21+ who are legal US residents living within 75 miles of Chicago city limits. Ends April 10, 2027 at 11:59 PM CST.
Enter once online at the Circa Win entry form during the promotion period.
Win $2,000 in value – Chicago Blackhawks Circa Win You Win Sweepstakes - 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
