Chicago Sweepstakes
Found 21 total
Chicago Gourmet Grand Cru Giveaway offers two tickets to Grand Cru, presented by UnitedHealthcare, featuring tastings from 30+ award‑winning chefs, valued at $510+ USD. The event takes place on Saturday, September 26, 2026, with a choice of a 2–5 PM or 7–10 PM session. One winner will be selected, and the entry period ends on September 16, 2026. - Two tickets to Grand Cru, presented by UnitedHealthcare, featuring tastings from 30+ award‑winning chefs, valued at $510+ USD. The event is on Saturday, September 26, 2026, with a choice of a 2–5 PM or 7–10 PM session. One winner. Entry period ends September 16, 2026.
Win $510 in value – Chicago Gourmet Grand Cru Giveaway - Enter Now
The Chicago Metal Factory Riot Fest Tix Sweepstakes is a sweepstakes that gives participants the opportunity to win a 3‑day Riot Fest ticket for the event at Douglass Park in Chicago, scheduled for September 18–20, 2026. The sweepstakes ends on September 14, 2026, at 11:59 AM CDT. - 3‑day Riot Fest ticket for Riot Fest at Douglass Park, Chicago, September 18–20, 2026.
Win $3,400 in value – The Chicago Metal Factory Riot Fest Tix Sweepstakes - 10 Winners - Enter Now
Guardian Heating and Cooling Service Fall Football Giveaway is offering one Ultimate Game-Day Package. The package includes two tickets to see the Chicago Bears take on the Philadelphia Eagles on Monday, September 28, 2026, and a $100 Visa gift card for game‑day fun. The giveaway ends on September 22, 2026. - One Ultimate Game-Day Package: two tickets to the Bears vs. Eagles game on September 28, 2026, and a $100 Visa gift card.
Win $400 in value – Guardian Heating And Cooling Service Fall Football Giveaway - Enter Now
Lipton Hard Iced Tea Buffalo Bills Ticket Giveaway offers the following prizes. - Entry Period 1: Two tickets to the Detroit Lions vs. Buffalo Bills game on September 17 and two tickets to the Gameday Hospitality tailgate experience. Transportation not provided (ARV $460). - Entry Period 2: Two tickets to the Los Angeles Chargers vs. Buffalo Bills game on September 27 and two tickets to the Gameday Hospitality tailgate experience. Transportation not provided (ARV $460). - Entry Period 3: Two tickets to the New England Patriots vs Buffalo Bills game on October 4 and two tickets to the Gameday Hospitality tailgate experience. Transportation not provided (ARV $460). - Entry Period 4: Two tickets to the Baltimore Ravens vs. Buffalo Bills game on November 1 and two tickets to the Gameday Hospitality tailgate experience. Transportation not provided (ARV $460). - Entry Period 5: Two tickets to the Miami Dolphins vs. Buffalo Bills game on November 22 and two tickets to the Gameday Hospitality tailgate experience. Transportation not provided (ARV $460). - Entry Period 6: Two tickets to the Kansas City Chiefs vs. Buffalo Bills game on November 26 and two tickets to the Gameday Hospitality tailgate experience. Transportation not provided (ARV $460). - Entry Period 7: Two tickets to the Chicago Bears vs Buffalo Bills game on December 19 and two tickets to the Gameday Hospitality tailgate experience. Transportation not provided (ARV $460). - Entry Period 8: Two tickets to the New York Jets vs. Buffalo Bills game on a date TBD and two tickets to the Gameday Hospitality tailgate experience. Transportation not provided (ARV $460). The promotion expires on January 3, 2027, at 11:59 PM EST.
Win $3,680 in value – Lipton Hard Iced Tea Buffalo Bills Ticket Giveaway - Enter Now
Eataly Chicago September Fest Ticket Giveaway. - Two (2) General Admission (GA) tickets to All You Can Eataly SeptemberFest at Eataly Chicago for Friday, September 18, 2026 (7:00 PM – 11:00 PM). Must be able to attend the event in person in Chicago, IL on September 18. Ending Date: Monday, September 14, 2026 at 12:00 PM CDT.
Win $250 in value – Eataly Chicago September Fest Ticket Giveaway - Enter Now
Toro Chicago Gourmet Weekend for Two Giveaway offers one Ultimate Chicago Gourmet Weekend Package for two. - One Ultimate Chicago Gourmet Weekend Package for two, containing two tickets to Chicago Gourmet’s Grand Cru Session Two (Saturday, September 26, 2026) and two tickets to the official Hamburger Hop After Party at Toro by Chef Richard Sandoval (Friday, September 25, 2026). The entry period ends in mid-September 2026.
Win $550 in value – Toro Chicago Gourmet Weekend for Two Giveaway - Enter Now
Chicago White Sox, Ltd. X Sweepstakes offers prizes that vary by individual Prompt Post, with an approximate retail value of $25 to $500 per prize; the date shown is September 30, 2026. - Prize varies by individual Prompt Post; each prize has an ARV of $25–$500.
Win $500 in value – Chicago White Sox, Ltd. X Sweepstakes - Enter Now
Enter the Taste The Movies: Ratatouille giveaway for a chance to win two tickets to an exclusive 7‑course immersive dinner in Chicago on September 25, 2026. Valued at approximately $300, the prize will be awarded to one lucky winner announced on September 22, 2026. To enter, follow @tastethemovies, like the post, tag the guest you’d bring, and share to your story for an extra entry. Open to 18+ residents of the United States. Don’t miss this cinematic dining experience—enter now!. This sweepstakes ends on September 22, 2026.
Win $300 in value – Taste The Movies Ratatouille - Enter Now
880 Ched All-Star Experience in Chicago: One (1) Grand Prize trip for two (winner and guest) to the 2027 MLB® All-Star Week in Chicago, Illinois (July 12–13, 2027). - Grand Prize includes round‑trip airfare to a Chicago, IL area airport, three (3) nights hotel accommodations in Chicago, two (2) tickets to the Home Run Derby (July 12) and the All-Star Game (July 13), and spending money (amount TBD). Entry period ends October 23, 2026, at 3:48 PM MST.
Win $15,000 in value – 880 Ched All-star Experience In Chicago - Enter Now
WTTW 2026 Be a Winner Sweepstakes offers approximately 74 prizes, including:
- Grand Prize: 2027 Subaru Crosstrek Hybrid — $36,000
- Road Scholar Kenya & Tanzania Safari for 2 — $21,800
- Oscar Isberian Rugs hand‑woven rug — $6,500
- The Barn on North private event for up to 50 guests — $5,000
- Fitness Formula Clubs 1‑year Signature Membership + 3 personal‑training sessions — $2,718
- Carnivale Chicago private party — 2 prizes, $2,500 each
- Home Carpet One cabinet gift certificate — $2,500
- Grand Hotel Mackinac Island stay — $900
- Edgewater Candles private candle‑making class — 4 prizes, $700 each
- Fleet Feet Chicago gift certificate + training voucher — $650
- Skydeck Chicago private Pie in the Sky dinner — $600
- Garrett Popcorn Family Tin + $500 eGift Card — $562
- Numerous additional restaurant, entertainment, fitness, travel, home, membership and gift‑card prizes
- Spring Early Bird prizes (2): Walla Walla Deluxe Wine Touring Package for 2 — $3,899 each
- Fall Early Bird prize: Weber Summit Smart Gas Grill — $5,299
- Bonus Prize: $10,000 gift card + in‑home design consultation — $10,100
ARV: $121,752 USD.
Ending Date: October 26, 2026.
*Free AMOE by postal mail.
Win $121,752 in value – WTTW 2026 Be a Winner Sweepstakes - Enter Now
