Penn Entertainment Announces Multi-Year Deal With the Chicago Bears
Posted on: August 20, 2025, 02:43h.
Last updated on: August 20, 2025, 02:43h.
- Penn receives entitlements for its two Chicago retail properties
- ESPN BET named Official Sports Betting Partner of the Bears
- ESPN BET now live in 20 U.S. jurisdictions
Penn Entertainment has announced a multi-year partnership with the NFL’s Chicago Bears, where the company’s retail properties Hollywood Casino Aurora and the new Hollywood Casino Joliet are designated Official Casino Partners, and ESPN BET Sportsbook is named an Official Sports Betting Partner of the Bears.

Multi-Year Deal
“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, Operations, 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. 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.”
Is Williams a Quality QB?
Maybe Penn is onto something. Few people are betting on the Bears as being a realistic Super Bowl bet. BetMGM has them at +4000 (1.8% of money), while the Bills currently have the shortest odds there at +700 (13.2% of money). At ESPN Bet the Bears are +3000 to win the Super Bowl.
Now the Bears pounded the Bills last weekend, 38-0, in both teams’ second pre-season game. The Bills were playing their third and fourth starters, to put that in perspective.
Hollywood Casino Joliet Opened Aug. 11
But sophomore QB Caleb Williams was impressive against the Bills, including leading the first-team offence on a seven-play opening drive for a touchdown, his first game playing new coach Ben Johnson and his offence. In 13 snaps over two drives, the former No. 1 overall pick went 6-for-10 for 107 yards. I was in an Uber car in Las Vegas last week driven by a guy from Chicago and he swears by his confidence in his lifelong favourite team, that they’re a serious up-and-comer.
Are they Under 8.5 wins, or Over, for this upcoming season? The Bears wrap up their pre-season Friday in Kansas City against the Chiefs.
In-Stadium Signage
No one is booking any parades, but the Bears are an up-and-coming team.
Plus, there’s the brand value behind the team. The Chicago Bears are one of the NFL’s most storied franchises. They are planning a new stadium as well, in Arlington Heights.
Under the agreement, Penn receives IP rights, in-stadium signage, an in-game Hollywood Casino feature, digital media and marketing integrations.
Hollywood Casino Joliet had its grand opening on Aug. 11, replacing the former riverboat location. That new property features 1,000 slots and 43 live table games, as well as an ESPN BET sportsbook.
ESPN Bet is live in 20 U.s. jurisdictions. New for this season, ESPN Bet has launched FanCenter, a personalized in-app hub that allows customers to easily find wager market based on their favourite teams, players and ESPN Fantasy rosters.
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