Win Chicago Cubs VIP Experience! (6 Winners)

The Chicago Cubs VIP Experience Sweepstakes gives baseball fans the chance to experience one of the sport's most iconic traditions—watching the Chicago Cubs play at historic Wrigley Field. This exciting free giveaway is sending six lucky winners to Chicago, Illinois, for an unforgettable game-day experience on August 15, 2026, where baseball history and passionate fandom come together.

A trip to Wrigley Field is about more than just seeing a game. It's the chance to sit among thousands of devoted fans, take in the legendary atmosphere, and witness the excitement of Major League Baseball in one of America's most beloved ballparks. From the ivy-covered outfield walls to the roar of the crowd after a big play, every moment feels like a celebration of the game.

Each winner will receive a premium trip to Chicago and the opportunity to watch the Cubs take the field in person. Whether you're a lifelong baseball fan or simply love unforgettable sports experiences, this VIP getaway promises memories that will last long after the final out.

Don't miss your chance to enter the Chicago Cubs VIP Experience Sweepstakes. With only six winners being selected, this exclusive giveaway could turn your love of baseball into the ultimate trip to the Friendly Confines. 

How to Enter the Chicago Cubs VIP Experience Sweepstakes

Method 1: Insurance Quote Entry

• Visit the Promotion Site during the Promotion Period
• Request an insurance quote for:

• Home insurance (1 entry), OR
• Auto insurance (1 entry), OR
• Bundled home + auto insurance (2 entries)
• Complete the online quote process
• Only one quote request per person is allowed for entry purposes
• No purchase is required

Method 2: Email Entry (No Quote Required)

• Send an email to: [email protected]
• Subject line: Chicago Cubs VIP Experience Sweepstakes
• Include in the email body:
• Full first and last name
• Home address
• Date of birth
• Eligible email entries receive 2 Sweepstakes entries

Entry Limit

• Maximum of two entries per eligible person
• Entrants must be 21 years of age or older
• Open only to legal residents of select U.S. states and jurisdictions

Winner Selection

Six winners will be selected in a random drawing on or about July 13, 2026, from all eligible entries received during the promotion period.

Prize Details

Six Grand Prize winners will each receive a premium Chicago Cubs VIP trip for two.

Grand Prize Includes (Per Winner):

• Round-trip coach airfare for two to Chicago, Illinois
• Two-night hotel accommodation (double occupancy, selected by Sponsor)
• Two suite tickets to the Chicago Cubs game on August 15, 2026
• Fulfillment via MLB mobile app
• Exclusive VIP experiences (subject to availability), including:

• Wrigley Field Press Box Experience
• Pregame Field Photo Passes
• Cubs Alumni Ambassador Meet & Greet
• One autographed Chicago Cubs baseball (details determined by Sponsor)
• One $100 Cubs Store gift card
• One $250 prepaid card (subject to terms and fees)

Approximate Retail Value (ARV): $7,550 per prize