Chicago Sweepstakes

Entered on:  - 1 Entries
Increment Entry Counter: Increment

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

Entered on:  - 1 Entries
Increment Entry Counter: Increment

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

Entered on:  - 1 Entries
Increment Entry Counter: Increment

Enter the Southwest Airlines Runway to Wrigley Sweepstakes for a chance to win an unforgettable prize package. The winner and their guest will receive a thrilling experience, including two tickets to a 2026 Chicago Cubs home game, a Wrigley Field Scoreboard viewing experience, 50,000 Southwest Airlines Rapid Rewards bonus points, a one-night hotel stay, and exclusive autographed memorabilia. The approximate retail value of the prize is $3,052.41. Don't miss this opportunity to win big with Southwest Airlines.

Win $3,052 in value – Southwest Airlines Runway to Wrigley Sweepstakes - Enter Now

Entered on:  - 1 Entries
Increment Entry Counter: Increment

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

Entered on:  - 1 Entries
Increment Entry Counter: Increment

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

Entered on:  - 1 Entries
Increment Entry Counter: Increment

Enter the Chicago White Sox Ultimate Fan Sweepstakes, presented by Chicago White Sox, Ltd., for a chance to win exciting prizes. Employees of Chicago White Sox, Ltd., MLB Entities, and their immediate family members are not eligible. To enter, visit whitesox.com/sweepstakes and complete the online entry form during one of the six entry periods, which run from March 14, 2026, to August 30, 2026. Limit one entry per person/email address. Six prizes will be awarded, including tickets to Chicago White Sox games, VIP access, and more, with a total approximate retail value of $13,000. Enter now for your chance to win and become the ultimate Chicago White Sox fan, courtesy of Chicago White Sox, Ltd.

Win $13,000 in value – Chicago White Sox Ultimate Fan Sweepstakes - 6 Winners - Enter Now

Entered on:  - 1 Entries
Increment Entry Counter: Increment

Enter to win exciting prizes in the Mountain Dew Rock The Mountain Sweepstakes, open to legal residents of IA, IL, IN, KS, MN, MO, NE, SD, and WI, 18+ (19 in NE). The promotion period runs from April 4, 2026, to October 4, 2026. Play the instant win game by scanning the code on participating retailer signage or visiting mountaindewpromos.com/rockthemountain. Limit one play per person, per email, per household per day. Win instant prizes like Mountain Dew Can Coolers, Speakers, Totes, Spotify subscriptions, and gift cards, with a total of 1,200 instant win prizes available. Additionally, be entered into the Grand Prize Drawing for a trip for two to a concert at the United Center in Chicago, IL, with five Grand Prizes available. The total ARV of all prizes is up to $64,066. Pepsi-Cola Company, the Sponsor, reserves the right to modify the promotion. Enter for free and follow the on-screen instructions to play and claim your prize if you win.

Win $63,000 in value – Mountain Dew Rock The Mountain Instant Win Game Sweepstakes - Enter Now