Chicago Sweepstakes
Found 21 total
College Avenue Student Loans presents the College Avenue Student Loans Ultimate Chicago Fire Experience Sweepstakes – a free entry giveaway where you can win an Ultimate Prize Pack.
- Customized team gear
- Pre‑match experience
- Two (2) field‑level tickets
- $1,000 Visa Gift Card
Enter to win before the sweepstakes ends on August 31, 2026 at 11:59:59 p.m. EDT.
Cabot Creamery Cooperative Boston Red Sox Giveaway – Enter for a chance to win amazing prizes! Free entry to this sweepstakes gives you the opportunity to win:
- 2 tickets to the Boston Red Sox game against Chicago at Fenway Park on Saturday, September 26, 2026
- $150 Cabot Creamery gift card (cabotcreamery.com)
- 2 Cabot ‘cheddar’ baseball hats
Total prize value $437.50. Contest ends August 23, 2026 at 11:59 p.m. Enter now for your chance to win! Brought to you by Cabot Creamery Cooperative.
Win $438 in value – Cabot Creamery Cooperative Boston Red Sox Giveaway - Enter Now
Enter the Giveaway Time from Windy City Chicago for a chance to win a Glow Revival facial treatment at The Spa at Palmer House plus a Dermaflash device. One lucky winner will be announced on August 30, 2026. The prize bundle is valued at approximately $270. To enter, like the post, follow @windy_citychicago and @thespaatpalmerhouse, and tag a friend in the comments. Open to participants 18+ in the United States. This sweepstakes is a great way to refresh your skin and enjoy a premium spa experience. This sweepstakes ends on August 30, 2026.
Win $270 in value – Windy City Chicago Giveaway Time - Enter Now
Enter the Yardbird Picnic Kit Giveaway for a chance to win a $150 Yardbird gift card plus the ultimate picnic kit—insulated cooler pack, blanket, tote bag, T‑shirt, hat and bottle opener. To enter, follow @yardbirdrestaurants and @keninchicago, like the post, tag two friends, and share to your story for a bonus entry. The giveaway ends August 31, 2026. Winners must be 21+ US residents with a public Instagram account. One winner will be announced on Instagram Stories. Good luck!
Win $150 in value – Yardbird Restaurants Picnic Kit Giveaway - Enter Now
Enter the Chicago Boat Cruise Giveaway for a chance to win a sunset cruise on a vintage Hinckley picnic boat in Chicago. Four winners and their guests will enjoy a fully captained two‑hour cruise on August 26, 2026, plus light bites, transport and exclusive Batiste merch gift bags – an estimated prize value of $1,300. To enter, follow @Batiste_us, like the post and tag a boat mate; bonus entries are earned by engaging with the three previous posts and using #Batiste_sweepstakes. The giveaway ends on 08-24-2026. Open to Illinois residents 18+ only. This sweepstakes ends on August 24, 2026.
Win $1,300 in value – Batiste Chicago Boat Cruise Giveaway - 4 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 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
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
