Penn Entertainment Announces Multi-Year Deal With the Chicago Bears

• Penn receives entitlements for its two Chicago retail properties
• ESPN BET named Official Sports Betting Partner of the Bears
• ESPN BET now live in 20 U.S. jurisdictions

Penn Entertainment has unveiled an exciting multi-year partnership with the NFL’s Chicago Bears. Under this collaboration, Penn’s retail venues, Hollywood Casino Aurora and the new Hollywood Casino Joliet, will serve as Official Casino Partners for the team. Additionally, ESPN BET Sportsbook has been designated as the Official Sports Betting Partner of the Bears.

Multi-Year Deal

“We’re excited to announce this partnership while also celebrating the opening of our state-of-the-art Joliet property, just in time for the football season,” said Todd George, Executive Vice President of Operations at Penn Entertainment.

“Collaborating with one of the most respected franchises in the NFL opens up fantastic marketing pathways for both our ESPN BET and Hollywood Casino brands. We’re keen to connect with a vast and passionate audience at Soldier Field and through our online platforms in the Chicagoland area.”

Future Prospects for the Bears

Despite the buzz around the partnership, analysts are still cautious. Few are betting on the Bears as strong contenders for the Super Bowl. Currently, BetMGM lists the Bears’ odds at +4000, with only 1.8% of the funds backing them, while the heavily favoured Bills sit at +700 (13.2% of the money). ESPN Bet shows the Bears at +3000 for the Super Bowl win.

The Bears recently made a statement by defeating the Bills 38-0 during their second pre-season match, showcasing their potential while the Bills fielded mostly third-string players.

Hollywood Casino Joliet’s Grand Opening

The Hollywood Casino Joliet opened its doors on August 11, 2025, to much anticipation, offering customers 1,000 slots and 43 live table games, along with an ESPN BET sportsbook. This new venue aims to capture the excitement around NFL games and provides an immersive gaming experience.

Caleb Williams, the Bears’ sophomore QB and first overall pick in the draft, put on an impressive performance against the Bills, completing 6-of-10 passes for 107 yards over two drives.

In-Stadium Branding Opportunities

The partnership also allows Penn to enhance its brand visibility through various in-stadium promotions, digital marketing efforts, and media rights in relation to the Bears. The Chicago Bears, known for their storied history in the NFL, are also working on building a new stadium in Arlington Heights, further increasing the franchise’s brand value.

With the strategic integration of in-game mentions, signage, and marketing strategies, Penn and the Bears aim to solidify their presence both online and offline, appealing to a new generation of fans as the NFL season approaches.

In summary, this partnership not only marks a significant step for both Penn Entertainment and the Chicago Bears but also illustrates the growing intersection between sports and gambling, setting the stage for a thrilling football season ahead.