Chicago Sweepstakes
Found 23 total
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 Chicago Metal Factory Win Ffdp Tix Sweepstakes for a chance to win exciting prizes. Ten lucky winners will receive FFDp tickets, courtesy of The Chicago Metal Factory. To enter to win, participate before the sweepstakes ends on August 12, 2026, at 01:02 PM CDT.
Win $750 in value – The Chicago Metal Factory Win Ffdp Tix 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 Cubs Game Day Sweepstakes for a chance to win an unforgettable trip to Chicago, Illinois. The grand prize includes a 3-day, 2-night trip for you and a guest, featuring round-trip air transportation, 2 nights of hotel accommodation in downtown Chicago, and 2 Club Level tickets to a Cubs game with a pre-game on-field tour. You'll also receive a $1,000 CB2 Gift Card to design your dream living room with the help of a dedicated Design Desk professional. The total prize value is approximately $5,000. To enter, participate before August 16, 2026, at 11:59 p.m. Eastern Standard Time. Don't miss this opportunity to win big with the Cubs Game Day MLB Sweepstakes.
Win $5,000 in value – CB2.com The Cubs Game Day Sweepstakes - 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 Cubs Take the Field with Toyota Sweepstakes for a chance to win an unforgettable experience. Ten lucky winners will each receive four tickets to a Chicago Cubs home game at Wrigley Field on September 1, 2026, plus the opportunity to play catch on the field with three guests after the game. With an approximate retail value of $500 per prize, the total prize value is $5,000. Note that transportation and lodging are not included. Don't miss this free entry MLB sweepstakes to win a prize that's a home run for any Cubs fan, courtesy of this Toyota Sweepstakes.
Win $5,000 in value – Cubs Take the Field with Toyota Sweepstakes - 10 Winners - Enter Now
Enter the Xfinity Rewards Zac Brown Band live in Chicago Sweepstakes for a chance to win an unforgettable experience. The prize package includes VIP tickets to a "Love & Fear Tour" show at Allstate Arena, three-day hotel accommodations, round-trip airfare, and VIP perks like priority check-in and a dedicated "fast lane" for merch shopping. Additionally, you'll receive a $600 prepaid gift card to cover extra expenses. The total prize value is approximately $3,350. Don't miss out - enter to win this amazing prize before the contest ends on August 16, 2026, at 11:59:59 p.m. ET.
Win $3,350 in value – Xfinity Rewards Zac Brown Band live in Chicago Sweepstakes - 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
