Chicago Sweepstakes
Found 24 total
Enter to win the House 15 Chicago Vintage $100 Store Credit Giveaway.
One winner gets $100 in House 15 store credit, good online or in the Chicago store.
Ends October 25, 2026 at 11:59 PM CDT; the winner is contacted directly by House 15.
To enter, follow House 15 | Chicago Vintage & Home Decor, like the giveaway post and tag friends in the comments (each comment counts as an entry); add the post to your story for an extra entry.
Win $100 in value – House 15 Chicago Vintage $100 Store Credit Giveaway - Enter Now
Enter to win the Virgin Gifts Murder Mystery Dinner Giveaway.
One winner gets an immersive murder mystery dinner experience in the US city of their choice (Atlanta, Chicago, Dallas, Denver and more).
Open to US residents 18 or older. No purchase necessary. Ends October 25, 2026 at 11:59 PM EDT; the winner is chosen October 26 and contacted by DM from @virgingiftsus.
To enter, like the @virgingiftsus giveaway post on Instagram, follow @virgingiftsus and tag your crime-solving sidekick (1 tag = 1 entry); share it to your stories for an extra entry.
Win $200 in value – Virgin Gifts Murder Mystery Dinner Giveaway - Enter Now
Enter to win the Diana Chicago Girls Coach Bag Giveaway.
One winner gets a vintage Coach signature monogram crossbody shoulder bag with leather trim and buckle detail.
For the Chicago area (the post is aimed at Chicago girls). Ends October 23, 2026 at 11:59 PM CDT.
To enter, follow @_princessdianaa__ on TikTok and follow the entry steps shown in the giveaway video. The winner is announced October 24, 2026 at 7 PM.
Win $250 in value – Diana Chicago Girls Coach Bag Giveaway - Enter Now
Enter to win the Chase Bandolik Bears Air Maxes Giveaway.
One winner gets a pair of Nike Air Max sneakers in Chicago Bears colors.
Open to US residents. Ends October 24, 2026 at 10:00 AM CDT.
To enter, like the giveaway video on TikTok and tag a Bears fan in the comments; every new tag is an extra entry, reposting earns 3 bonus entries and sharing to your story earns 5.
Win $150 in value – Chase Bandolik Bears Air Maxes 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 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.
