August 21, 2025 2 min read

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Penn Entertainment Secures Major Deal with Chicago Bears

The deal comes just after the opening of the new Hollywood Casino Joliet property and shortly before the start of the NFL season

Penn Entertainment, a leading casino and hospitality company in the US, has unveiled a new multi-year partnership with the Chicago Bears, a professional football team. The agreement comes just in time for the new NFL season.

A Multi-Faceted Agreement

According to the announcement, Penn’s ESPN BET Sportsbook will become an official sports betting partner of the Bears. Additionally, Penn’s Chicagoland retail properties, the upcoming Hollywood Casino Aurora and the brand-new Hollywood Casino Joliet will become official partners of the team.

For context, the new Hollywood Casino Joliet opened on August 11. The new property replaced the previous riverboat casino, marking a new chapter for casino gaming in the city. Bears executives and Joliet-born NFL legend Tom Thayer were present at the ribbon-cutting ceremony, reflecting the new partnership.

Under the deal with the Bears, both Penn’s land-based and online betting businesses will secure a variety of entitlements, such as Chicago Bears IP rights, in-stadium presence, an in-game Hollywood Casino feature, as well as multiple media and marketing integrations.

Penn’s customers, on the other hand, can look forward to a variety of Chicago Bears-themed experiences.

Penn Hopes to Engage the Bears’ Passionate Audience

Penn Entertainment’s executive vice president of operations, Todd George, said that his team is excited to unveil this tie-up, which comes just in time for the opening of his team’s new Hollywood Casino Joliet property and shortly before the start of the NFL season.

According to George, the partnership with one of the premier franchises in the NFL will provide his company’s Hollywood Casino and ESPN BET brands with “exciting new omnichannel marketing opportunities.”

Through the partnership, we look forward to engaging a large and passionate audience at Soldier Field as well as across our online products and at the new property in the Chicagoland area.

Todd George, EVP of operations, Penn Entertainment

In other Penn Entertainment-related news, the company’s ESPN BET brand was just forced to introduce a $1 bet minimum in Illinois due to the state’s recent tax hike.

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