Penn Entertainment just locked down a multi-year deal with the Chicago Bears. The agreement makes ESPN Bet the team’s Official Sports Betting Partner.
But that’s not all. Penn’s Chicagoland casinos also got pieces of the action.
Hollywood Casino Aurora and Hollywood Casino Joliet both became Official Casino Partners. The timing works perfectly with Penn’s brand new Joliet property, which opened August 11.
Why This Deal Makes Business Sense
Penn’s timing couldn’t be better. Football season’s about to kick off, and they’re connecting with one of the NFL’s biggest fan bases.
“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, Penn’s EVP of Operations.
The Bears bring a massive, passionate audience. That’s exactly what Penn needs for both its online ESPN Bet platform and physical casino locations.
George called it a chance to create “exciting new omnichannel marketing opportunities.” Translation: they can reach fans everywhere.
What Penn Gets from the Partnership
The deal covers both ESPN Bet and Hollywood Casino brands. Penn receives IP rights to use Bears branding and logos.
Soldier Field will feature in-stadium signage for Penn’s brands. There’s also an in-game Hollywood Casino feature planned.
Digital marketing integrations are part of the package too. Penn can offer exclusive team-related experiences to customers.
The new Hollywood Casino Joliet replaced the old riverboat location. It features about 1,000 slot machines and 43 live table games. There’s also an ESPN Bet sportsbook on-site.
Bears executives attended the August 11 ribbon cutting. Former Bears player Tom Thayer, a Joliet native, was there too.
How This Fits Penn’s Broader Strategy
Penn’s been pushing hard into sports betting through ESPN Bet. This partnership gives them major visibility in a key market.
The company released Q2 2025 results on August 7. They showed a $18.3 million net loss but record performance in interactive gaming.
Their retail operations stayed strong. The Bears partnership should help both sides of Penn’s business.
Chicago’s a massive sports betting market. Penn now has prime access through one of the city’s most popular teams.
The deal creates multiple touchpoints with fans. From the stadium experience to online betting, Penn’s brands will be everywhere Bears fans look.
This partnership positions Penn to capitalize on NFL season excitement while promoting their newest casino property.
