Chicago Sweepstakes
Found 13 total
Art Deco Nutcracker Experience Giveaway offers tickets to the full Art Deco Nutcracker Ballet performance and a one‑night hotel stay in a King Room at Sofitel Chicago Magnificent Mile. - Tickets to the full Art Deco Nutcracker Ballet performance. - One‑night hotel stay in a King Room at Sofitel Chicago Magnificent Mile. The estimated retail value of the prize package is $650. The sweepstakes ends on November 11, 2026 at 11:59 PM CST.
To enter, follow @sofitelchicago, @aaballetcenterfordance, and @theathenaeum_chicago, like the post, and tag who you'd bring along (each comment counts as one entry).
Win $650 in value – Art Deco Nutcracker Experience Giveaway - Enter Now
Enter to win the Do312 Adler Planetarium Chicago Staycation Giveaway.
One winner gets 2 Adler Planetarium museum and Dome Show tickets, Adler merch, a 1-night stay at Hotel Lincoln and a 1-year DoMORE membership. No value is stated; estimated about $400.
No eligibility is stated; the prize is in Chicago IL. Ends 11-15-2026 6:00 PM CST.
To enter, fill out the giveaway form on the do312.com Adler Planetarium Staycation page (linked from @do312's bio). Winner chosen after November 15, 2026.
Win $400 in value – Do312 Adler Planetarium Chicago Staycation Giveaway - Enter Now
Enter to win the Fairmont Chicago The Ultimate Chicago Holiday Getaway Giveaway.
Fairmont Chicago The Ultimate Chicago Holiday Getaway Giveaway offers a single winner a holiday package. - 5 VIP viewing stand tickets to the Wintrust Magnificent Mile Lights Festival® on November 21, providing a front‑row view of the festivities, fireworks, festive surprises and holiday gifts. Total value $1,500.
No eligibility stated. Ends November 11, 2026 11:59 PM EST.
To enter, follow @fairmontchicago and @themagmile, like the post and comment on the post. The winner is picked after the giveaway ends.
Win $1,500 in value – Fairmont Chicago The Ultimate Chicago Holiday Getaway Giveaway - Enter Now
Enter to win the Throwback 100.3 Backstreet Boys at Sphere NYE Sweepstakes.
Prize: 2 tickets to the Backstreet Boys at Sphere in Las Vegas on December 31, 2026, round-trip airfare for 2 from Chicago ORD and 2 hotel nights (ARV $2500, 1 winner).
Open to residents 21+ of the Chicago-area counties in IL, Kenosha County WI and Lake and Porter counties IN. Runs November 2 - November 27, 2026 at 11:59 PM CT.
To enter, listen to Throwback 100.3 WTBC for the code word announced 5 times a day and submit it in the station stream player or app during that daily entry period.
Win $2,500 in value – Throwback 100.3 Backstreet Boys at Sphere NYE Sweepstakes - Enter Now
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 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 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 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.
