Chicago Sweepstakes
Found 22 total
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 Tom Kelly's Chophouse & Pub Bears Ticket Giveaway.
One winner receives 2 Miller Lite Loft admission tickets (unassigned seats) for the Chicago Bears vs. New England Patriots Thursday Night Football game at Soldier Field on October 22, 2026; food, beverages, parking and transportation are not included.
Must be 18+ to enter (21+ to buy alcohol). Entries close Wednesday, October 21, 2026 at 12:00 PM CT.
To enter, follow Tom Kelly's Chophouse & Pub on Instagram and comment on the giveaway post telling who you'd bring. The winner is drawn October 21, 2026.
Win $300 in value – Tom Kelly's Chophouse & Pub Bears 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 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
