Chicago Sweepstakes
Found 19 total
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 Chicago’s About Get Loud Giveaway from Insta360 for a chance to win two cutting‑edge cameras – a Luna Ultra (≈$300) and an Insta360 Ace Pro (≈$199) – a total prize value of $499. Two winners will be randomly selected, one per prize, and the contest ends August 10, 2026. Open to U.S. residents 18+, entry requires following @insta360_usa, liking, reposting, commenting with a festival moment and tagging friends, plus a bonus entry using #FestivalWithInsta360. No purchase necessary.
Win $499 in value – Insta360 Chicago’s About Get Loud Giveaway - 2 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
Enter the C4 Energy x Chicago Fire Tickets Sweepstakes for a chance to win an exciting prize package. Score big with four tickets to the Chicago Fire FC® game on September 14, 2026, plus four custom Chicago Fire FC® jerseys and a Visa® gift card. The total prize value is $1,060.00 USD. Don't miss out - enter to win this amazing giveaway before it ends on August 31, 2026, at 11:59 PM CT.
Win $1,060 in value – C4 Energy x Chicago Fire Tickets Sweepstakes - Enter Now
Enter the Margaritaville at Sea + Zac Brown Band National Contest for a chance to win exciting prizes. Up to 27 Market Winners will receive a pair of tickets to see Zac Brown Band live in various cities, including Pittsburgh, New York, Philadelphia, Kansas City, Miami, Greenville, Greensboro, Denver, and Chicago, with ticket values ranging from approximately $339.04 to $694.18. One Grand Prize Winner will receive a prize valued at up to $3,000.00. The contest is open through approximately 12:59 am (ET) on Monday, November 2, 2026. Don't miss this opportunity to win a free prize and experience the thrill of a live concert, courtesy of Margaritaville at Sea. Enter to win now and take a chance at an unforgettable experience with Margaritaville at Sea.
Win $3,000 in value – Margaritaville at Sea + Zac Brown Band National Contest - Enter Now
Get ready to win big with the Jewel-Osco Party the USA Sweepstakes, celebrating 250 years in style. Enter to win an incredible prize package worth over $3,800, featuring a two-night hotel stay at the Sable Hotel Navy Pier, a dinner cruise experience, Navy Pier Passport, Centennial Wheel Ride access, 360 Chicago Observation deck tickets, a family-sized tin of Garrett Popcorn, and a $250 Jewel-Osco Gift Card. Plus, every entry supports Operation Support Our Troops. Jewel-Osco is giving away this amazing prize package to lucky winners, so enter now for your chance to win and support a great cause with Jewel-Osco.
Win $3,800 in value – Jewel-Osco Party the USA Sweepstakes - 5 Winners - Enter Now
Enter the Crate & Barrel The Bear Sweepstakes for a chance to win an exciting prize package. No purchase necessary to enter or win. The sweepstakes starts on 6/16/2026 and closes on 8/11/2026. To enter, fill out the online form or mail a 3x5 inch paper with your contact information to the address provided. One entry per person. The grand prize includes round-trip flights to Chicago, a 3-night stay, dinner, and tickets to a Chicago experience, $1,000 spending money, a $1,000 Crate & Barrel Gift Card, and more. Enter now for a free chance to win. Sponsored by Euromarket Designs, Inc. d/b/a Crate & Barrel, and Crate & Barrel Canada, Inc., the Crate & Barrel The Bear Sweepstakes is a giveaway you won't want to miss.
Win $6,800 in value – Crate & Barrel The Bear Sweepstakes - Enter Now
