• PENN Entertainment has signed a multi-year partnership with the NFL’s Chicago Bears, making ESPN BET the team’s official sports betting partner.
• The deal also names PENN’s land-based Hollywood Casino properties in Joliet and Aurora as the team’s official casino partners, creating a strong omnichannel link.
• The partnership includes extensive marketing rights, such as in-stadium signage at Soldier Field, digital activations, and use of the Bears’ official trademarks.
• The timing is strategic, coinciding with the start of the NFL season and the recent opening of PENN’s new, state-of-the-art Hollywood Casino Joliet.
• The move is a key part of PENN’s strategy to leverage the ESPN media brand and local partnerships to compete in the highly competitive Illinois market.

PENN Entertainment has secured a major new partnership with the NFL’s Chicago Bears, in a move that deeply integrates both its digital and retail brands with one of the league’s most iconic franchises. The multi-year agreement names ESPN BET as the team’s official sports betting partner and the Hollywood Casino brand as its official casino partner.

The deal is a textbook execution of PENN’s omnichannel strategy, designed to create a powerful marketing loop between its growing ESPN BET online platform and its established, state-of-the-art land-based properties in the key Illinois market.

Timed for Maximum Impact

The timing of the announcement is particularly strategic. It comes just weeks before the start of the NFL season, the most critical period for customer acquisition for US sportsbooks. It also coincides with the grand opening of PENN’s new land-based Hollywood Casino Joliet, a modern property that replaces the company’s old riverboat casino and features a prominent ESPN BET sportsbook lounge.

“We’re thrilled to announce this partnership in connection with the opening of our new state-of-the-art Joliet property and on the precipice of football season,” said Todd George, Executive Vice President of Operations for PENN Entertainment. “Teaming up with one of the premier franchises in the NFL creates exciting new omnichannel marketing opportunities for our ESPN BET and Hollywood Casino brands.”

Deepening Roots in a Key Market

The partnership provides PENN with a full suite of marketing and branding rights, including highly visible in-stadium signage at the Bears’ home ground, Soldier Field, as well as digital and social media activations. This will give the ESPN BET brand a powerful platform to engage with Chicago’s passionate fanbase and compete more effectively in one of the largest and most competitive regulated betting markets in the United States.

The Broader PENN Strategy

This deal is a key piece of PENN’s wider national strategy, which centres on leveraging the immense media power of ESPN and integrating it with its retail casino footprint. The company has been rolling out new in-app features like the FanCenter, which personalises betting markets for users based on their favourite teams, and is continuing to invest heavily in its land-based portfolio, with a new Hollywood Casino Aurora also slated to open in 2026.

The Chicago Bears partnership is another clear signal of PENN’s intent to build a fully integrated, media-driven, and locally-focused gaming and entertainment ecosystem.