Chicago Sweepstakes
Found 18 total
Chicago Golf Gals Four Complimentary Spots Giveaway offers a winning foursome of four complimentary spots valued at $720, including a 9‑hole scramble with a golf cart, range balls, a dinner reception, an on‑course drink ticket, contest holes and raffles, and player tee gifts. The giveaway closes on 9/25 at 11:59 pm CST.
Win $720 in value – Chicago Golf Gals Four Complimentary Spots Giveaway - Enter Now
Goodreads (eBook) My Darling Girls Book Giveaway – Enter the Goodreads giveaway for My Darling Girls by Marina Scott. In 1904 Chicago, secrets cling as thickly as the soot on every windowsill, and Jo earns her living by photographing the dead. Her work is quiet and cloistered, allowing her to hide from a past that haunts her with grief over her husband’s mysterious death, a spiraling addiction, and the guilt she carries for the things she has done to survive. When a notorious crime family hires Jo to make a final portrait of their daughter Millie, it stirs up a spirit that refuses to rest. In opium‑fueled dreams, Millie lures Jo into a realm called “the courtyard,” where the dead burn to tell their half‑finished stories. As Jo investigates Millie’s murder, she forms a fragile bond with her sister Grace, who is desperate for an escape of her own. Amid the whispers of the dead, Jo must confront a truth if she is to free them all from the shadows of the past.
Win $500 in value – Goodreads (eBook) My Darling Girls Book Giveaway - Enter Now
Gorilla Energy Drink VIP Fight Experience Sweepstakes ends on 08 October 2026 at 11:59 PM CDT. The winner(s) will receive the following prizes:
- One winner will receive a Full VIP PFL Chicago Experience plus Exclusive MMA gloves (approximate retail value $1,600).
- One winner will receive a $500 Visa Gift Card and a free Gorilla Energy three‑month supply (approximate retail value $500).
- One winner will receive a free Gorilla Energy three‑month supply (approximate retail value $100).
Win $2,200 in value – Gorilla Energy Drink VIP Fight Experience Sweepstakes - Enter Now
Goodreads (eBook) You're the Cream in My Coffee Book Giveaway provides a free digital copy of Jennifer Lamont Leo’s novel You’re the Cream in My Coffee. Set in 1928 Chicago during the Jazz Age and Prohibition, the story follows small‑town girl Marjorie Corrigan who, after spotting her presumed‑dead high‑school sweetheart at a train station, moves to the city, takes a department‑store job, and becomes entangled in a world of speakeasies, fashion, and mystery. As she tries to uncover the truth about the stranger, she must choose between her fiancé, a young doctor, and the alluring lifestyle of her roommate Dot, while strange events unfold at the store’s loading dock late at night.
Win $500 in value – Goodreads (eBook) You're the Cream in My Coffee Book Giveaway - Enter Now
The 2026 Stella Blue Coffee Fall Kickoff Sweepstakes ends on September 27th, 2026 at 11:59 PM ET. There will be three (3) prizes awarded. Each prize consists of a Chicago HQ office visit on a mutually agreed upon date in Fall 2026, a $500.00 USD travel stipend, and $500.00 USD worth of free Stella Blue coffee and Barstool Sports merchandise for the winner and one (1) guest. - One winner and one guest will receive a Chicago HQ office visit, a $500 travel stipend, and $500 of Stella Blue coffee and Barstool Sports merchandise. - One winner and one guest will receive a Chicago HQ office visit, a $500 travel stipend, and $500 of Stella Blue coffee and Barstool Sports merchandise. - One winner and one guest will receive a Chicago HQ office visit, a $500 travel stipend, and $500 of Stella Blue coffee and Barstool Sports merchandise. All prizes must be redeemed within 365 days or they will be automatically forfeited. The aggregate actual retail value of all combined prizes is $3,000.00 USD ($1,000.00 USD ARV per winner). All details regarding the prize, including date, time, itinerary, entry conditions, health and safety policies, and any other matters, are determined at the Sponsor’s sole discretion and may be modified by the Sponsor at any time.
Win $3,000 in value – The 2026 Stella Blue Coffee Fall Kickoff Sweepstakes - Enter Now
Eli’s and Jewel National Cheesecake Day 40 Sweet Years Together Sweepstakes offers a Grand Prize and a First Prize Award. - Grand Prize: a one‑year supply of Eli’s Cheesecakes (one cheesecake delivered each month for twelve consecutive months, for a total of twelve cheesecakes) plus a private, behind‑the‑scenes tour of Eli’s Cheesecake’s Bakery in Chicago, Illinois for four guests aged 10 and over. Transportation is not included; the winner must arrange and pay for all travel costs, including flights, hotels, ground transport, meals, and any other expenses. The tour must be conducted within six months of the sponsor’s announcement of the Grand Prize winner, and the winner will be given six date and time options to select from. Closed‑toe shoes are required, safety gear will be provided on‑site, and the winner and guests must sign a liability waiver before entry. Each cheesecake will be shipped frozen, packaged with dry ice in a protective container, and flavors may vary. The total approximate retail value of the Grand Prize package is $1,194 (cheesecake value $794, tour value $400). - First Prize Award (39 winners): each winner receives one 9‑inch Eli’s Original Favorite Sampler Cheesecake shipped frozen, packaged with dry ice in a protective container and delivered to the winner’s door. Cheesecake flavors may vary. The approximate retail value per prize is $86, for a total ARV of $4,548 for all 39 First Prize Awards. The sweepstakes ends at 12:59 PM Central Time (CT) on September 30, 2026.
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
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
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
