Chicago Sweepstakes
Found 21 total
Enter to win a 1-Week Pure Barre Pass! Chicago Moms is giving 10 lucky winners the chance to enjoy unlimited Pure Barre classes for one week. Giveaway ends Friday, August 21, 2026, at 11:59 PM EST.
Win $550 in value – Chicago Moms 1-week Pure Barre Pass Giveaway - 10 Winners - Enter Now
Enter to win the Kempersports Frequent Fairways Chicagoland Program Private Course Round Contest for a chance to score a coveted golfing experience. Two lucky winners will be randomly selected from eligible entries received by October 31, 2026. Each winner will receive a prize package worth $800, consisting of one round of golf (greens fees and cart) for up to four players at either The Royal Melbourne Country Club or Hawthorn Woods Country Club, as chosen by the Sponsor. With a total prize value of $1,600, this giveaway is a hole-in-one for golf enthusiasts. Submit your free entry now and take a swing at winning a fantastic golfing prize, courtesy of Kempersports. Free postal mail AMOE in rules.
Enter to win the Goodreads (Print) The Responsible Party Book Giveaway and discover a captivating tale of resilience and survival. Claire Carusillo's novel follows the legend of the Unsinkable Mounsey Women, from a Liverpudlian poorhouse in WWI to a Lake Michigan lighthouse in 1971 and present-day Chicagoland. With a rich history of improbable survivals, vaudeville success, and complicated women, this book is a must-read. Enter the Goodreads giveaway for a free chance to win and dive into the story of Claire and her descendants as they navigate love, loss, and family secrets. Goodreads brings you this exciting book giveaway, so enter now and take a chance to win The Responsible Party by Claire Carusillo.
Win $675 in value – Goodreads (Print) The Responsible Party Book Giveaway - Enter Now
Enter to win The Kimpton Gray Hotel Ultimate 10th Anniversary Package Giveaway for a chance to experience the ultimate getaway. This incredible prize package includes a 2-night stay at The Kimpton Gray Hotel in Chicago and a 2-night stay at the Journeyman Hotel in Milwaukee. Enjoy complimentary cocktails at Vol. 39 and The Outsider Rooftop, plus a $400 dining credit to savor the flavors of Boleo and Tré Rivali Restaurant. You'll also receive a $200 additional dining credit and a $100 Amtrak gift card for round-trip travel. To top it off, curated local welcome kits await at both hotels, showcasing the best of Chicago and Milwaukee. Don't miss out - enter for free now through Monday, August 17, 2026.
Win $2,000 in value – The Kimpton Gray Hotel Ultimate 10th Anniversary Package Giveaway - Enter Now
Enter to win The Kimpton Gray Hotel Dining Credit Giveaway for a chance to score an unforgettable Midwest getaway valued at over $2,000! Celebrating a decade of iconic properties, one lucky winner and a friend will enjoy a 2-night stay at The Kimpton Gray Hotel in Chicago and The Kimpton Journeyman Hotel in Milwaukee. The prize package includes complimentary cocktails, a $400 dining credit to Boleo & Tre Rivali Restaurant, a $200 additional dining credit, a $100 Amtrak Gift Card, and curated local welcome kits. Enter now for your free chance to win this incredible prize, available until 8/17/2026.
Win $2,000 in value – The Kimpton Gray Hotel Trip Giveaway - Enter Now
Enter the Audacy Riot Fest Sweepstakes for a chance to win an epic trip to Chicago, IL. The grand prize includes roundtrip airfare for two, four nights of hotel accommodations, and two 3-Day VIP Passes to Riot Fest, valued at up to $4,000.00. Provided by Republic Records, this prize package is the ultimate experience for music fans. To enter to win, simply participate in the Audacy Riot Fest Sweepstakes before the deadline. The trip winner and their guest must be 18 or older, and ground transportation and incidentals are not included. Don't miss your chance to win this incredible prize, courtesy of Audacy.
Win $4,000 in value – Audacy Riot Fest 2026 Trip Sweepstakes - Enter Now
Enter the Vienna Beef and Chicago Cubs Sweepstakes for a chance to win exciting prizes. One lucky winner will receive a First Prize package worth $1,100, including four Chicago Cubs game tickets, a personalized Cubs jersey, and a $250 ViennaBeef.com gift card. Other prizes include autographed Cubs memorabilia, signed and unsigned Vienna Beef and Wrigley Field posters, and Chicago Cubs x Vienna Beef hats. With a total of 50 winners and a total prize value of $9,100, don't miss your chance to win big with Vienna Beef and the Chicago Cubs.
Win $9,100 in value – Vienna Beef and Chicago Cubs Sweepstakes - 50 Winners - Enter Now
Get ready to win the captivating novel, The Innkeeper's Wife by Siobhan Hartsell, in the Goodreads (eBook) The Innkeeper's Wife Book Giveaway. Set against the backdrop of the Great Chicago Fire, this sweeping tale follows Bertha Honoré Palmer as she navigates a world of uncertainty and forges a path of renewal and influence. From the ashes of the city to the glittering rooms of the Palmer House and the 1893 World's Columbian Exposition, Bertha's story is one of duty, marriage, and power. Enter to win this gripping eBook and discover how one woman made history.
Win $1,000 in value – Goodreads (eBook) The Innkeeper's Wife Book Giveaway - Enter Now
Enter the Embassy Suites by Hilton Scottsdale Resort Ultimate Scottsdale Getaway Giveaway for a chance to win an unforgettable prize package! Score big with a one-night stay for two at Embassy Suites Scottsdale and catch the action with two lower-level tickets to the Arizona Diamondbacks vs. Chicago Cubs game on August 24. Don't miss out - enter to win this amazing giveaway before it closes on August 19 at 11:59 PM.
Enter the Flyyeg Night At The Races Contest for a chance to win an exciting travel prize. One lucky winner will receive a flight certificate redeemable at Paull Travel for two non-stop economy class round-trip flights to a destination of their choice, including Chicago, Houston, San Francisco, Las Vegas, Cancun, Puerto Vallarta, Reykjavik, or Montego Bay, with a maximum value of $4,500. Don't miss out - enter to win this amazing prize before the contest ends on September 14, 2026.
Win $4,500 in value – Flyyeg Night At The Races Contest - Enter Now
