PENN strikes multi-year partnership with Chicago Bears
PENN Entertainment has expanded its Illinois footprint with a new partnership with the Chicago Bears, making both its casino and sportsbook brands official team partners.
As part of the deal, Hollywood Casino Joliet and Hollywood Casino Aurora become the Bears’ casino partners, while ESPN BET takes on the role of sports betting partner, giving the brand added visibility with Chicago’s loyal fanbase.
The deal includes a full suite of marketing and branding rights, such as in-stadium signage at Soldier Field, use of the Bears’ trademarks, and a new “Hollywood Casino feature” on game days. PENN will also benefit from digital activations, including social media and online campaigns that offer fans exclusive team-related experiences.
Todd George, executive vice president of operations for PENN Entertainment, said that the agreement felt particularly well-timed. “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,” George commented. “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.”
George added that the company is eager to build closer connections with Chicago’s football faithful, both at Soldier Field and through PENN’s growing online ecosystem.
ESPN BET’s expanding reach
In securing the Bears’ partnership, ESPN BET enhances its strategy of tapping into local fan bases across major U.S. states. The digital sportsbook is now live in 20 jurisdictions, including Illinois, where it looks to combine the strength of ESPN’s media platform with personalised betting tools.
Earlier this summer, PENN rolled out FanCenter, an in-app hub that tailors betting options to individual preferences. Users can now see markets tied to their favorite teams, players, or even fantasy football rosters on ESPN platforms, bringing media and betting closer together.
The timing is notable: alongside the Bears partnership, PENN has just opened Hollywood Casino Joliet, a modern land-based property that takes over from its long-serving riverboat casino, establishing the company’s continued investment in Chicagoland.
Located within the Rock Run Collection development, a mixed-use complex that blends retail, residential, and leisure facilities, the new Joliet casino reflects PENN’s modernisation strategy. The property features roughly 1,000 slot machines, 43 table games, and a prominently positioned ESPN BET sportsbook lounge, bringing together land-based and digital betting under one roof.
A further expansion is on the horizon, with construction now underway on a new Hollywood Casino Aurora development. Slated to welcome guests in the first half of 2026, the Aurora site aims to deliver a similar combination of gaming, hospitality, and sports betting amenities.
Market response and strategic significance
Wall Street reacted modestly positively to news of PENN’s latest move. Shares in PENN Entertainment closed Thursday’s trading session in New York up 1.77 per cent at $19.00, suggesting investors view the partnership as another step toward reinforcing the company’s Midwest positioning and advancing its national profile.
For PENN, the Bears agreement is about more than logos and sponsorship rights. It ties Hollywood’s casinos to ESPN BET’s digital arm, giving the operator reach from the local level up to the national stage, all while planting a firmer flag in Illinois’ cut-throat betting market.
For the Bears, the alliance provides a new avenue for fan engagement, blending casino entertainment with the team experience, while guaranteeing a valuable sponsorship stream in a year when NFL franchises continue to strike deals with sportsbook operators.
With the NFL season just around the corner, PENN will be keen to maximise visibility from day one, and ensure its new Joliet flagship is firmly on the map for Chicago’s army of football fans.
