Penn Entertainment has entered into a multi-year agreement with the Chicago Bears, combining casino entertainment, sports betting, and professional football. The deal cements Hollywood Casino Aurora and the newly launched Hollywood Casino Joliet as the Official Casino Partners of the Bears, while ESPN Bet assumes the role of Official Sports Betting Partner.

The agreement lays the groundwork for fresh fan experiences across digital and in-person platforms, reinforcing Penn’s growing footprint in Illinois. Through the collaboration, Penn will benefit from branding visibility inside Soldier Field, digital advertising opportunities, and an in-game Hollywood Casino feature. Customers can also look forward to exclusive Chicago Bears experiences blending casino entertainment with the thrill of NFL football.

Joliet’s Grand Opening Sets the Stage

The announcement follows the opening of the new Hollywood Casino Joliet, which debuted on August 11, 2025. The land-based property replaces its riverboat predecessor, offering a modern facility at the Rock Run Collection commercial development. With 1,000 slot machines, 43 table games, an ESPN Bet sportsbook, multiple dining options, and an event center, the venue is positioned as a premier entertainment hub in the region.

The ribbon-cutting ceremony featured Chicago Bears executives alongside former NFL guard Tom Thayer, highlighting the significance of the Bears partnership. Beyond gaming, the new facility provides improved parking and access, ensuring convenience for visitors from neighbouring llinois communities.

ESPN Bet and Aurora Expansion on the Horizon

As part of the agreement, ESPN Bet solidifies its presence in Illinois as the Bears’ Official Sports Betting Partner. The platform has been expanding rapidly since its launch. Their newest feature, FanCenter, offers bettors a personalised hub, tailoring odds and experiences to users’ favorite teams, players, and fantasy football selections.

Meanwhile, construction is underway on the Hollywood Casino Aurora, scheduled to open in the first half of 2026. The development will bring a state-of-the-art gaming and hospitality experience to the Aurora market. This further aligns with Penn’s strategy to anchor itself in Illinois through major entertainment destinations. Together with Joliet, the Aurora site will strengthen Penn’s position in the region while providing Bears fans with new ways to engage.

A New Chapter for Penn and the Bears

For Penn Entertainment, the agreement represents a natural progression of its strategy of combining iGaming platforms and professional sports partnerships with a unified entertainment ecosystem. The Bears bring new opportunities to connect with fans inside Soldier Field and strengthen loyalty using digital channels and live activations. 

As Hollywood Casino Joliet begins operations and ESPN Bet grows nationally, Penn’s collaboration with the Bears is a new era for integrated sports and gaming experiences. The move is made in Illinois but for a fan base extending far beyond the state’s borders.