PENN Entertainment Secures Chicago Bears Partnership

As part of the deal, ESPN Bet has been named the Bears' Official Sports Betting Partner.

Ziv Chen

Last Updated: August 21, 2025 1:20 PM EDT • 2 minute read

PENN Entertainment Secures Chicago Bears Partnership — Pictured: Detailed view of a Chicago Bears helmet. Photo by Mark J. Rebilas via Imagn Images.

PENN Entertainment has signed a multi-year agreement with the Chicago Bears, making Hollywood Casino Aurora and Hollywood Casino Joliet the NFL team's Official Casino Partners.

As part of the deal, ESPN BET has been named the Bears' Official Sports Betting Partner, further strengthening PENN's presence in the Illinois sports betting market.

The partnership provides PENN with branding rights inside Soldier Field, digital advertising placements, and an in-game Hollywood Casino feature. It also includes exclusive Chicago Bears-themed experiences available to fans through both online platforms and on-site activations.

“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.”

The partnership coincides with the launch of the newly developed Hollywood Casino Joliet on Aug. 11. The land-based facility, which replaces its former riverboat location, is part of the Rock Run Collection commercial development.

The property has 1,000 slots, 43 table games, a number of restaurants, an events center, and an ESPN BET-brand sportsbook for people who prefer a brick-and-mortar choice over an Illinois sports betting app. Chicago Bears executives and ex-player Tom Thayer took part in the ribbon-cutting ceremony.

At the same time, the new Hollywood Casino Aurora is under construction, with a planned opening in the first half of 2026. With the casino projects, ESPN Bet has grown into 20 legal sports betting states.

NFL and ESPN expand partnership

The PENN-Bears partnership aligns with a broader shift in how the NFL and ESPN are expanding collaboration. Earlier this month, ESPN reached an agreement to acquire NFL Network, RedZone's linear distribution, and NFL Fantasy, among other NFL assets, in a deal valued at more than $1 billion. In return, the NFL will secure a 10% equity stake in ESPN.

The agreement includes two stages. First, ESPN will take over ownership and daily operations of NFL Network, RedZone's pay-TV channel, and NFL Fantasy. The latter will be integrated into ESPN's fantasy football platform.

Second, ESPN will license certain rights back to the NFL, maintaining NFL Network's annual slate of seven live games. The agreement includes three new games explicitly added for ESPN and the transfer of four more games from other outlets.

NFL ownership has yet to vote on the transaction. The league's commissioner, Roger Goodell, notified team owners that a virtual meeting to review the agreements is scheduled for Aug. 26.

Written by:
Ziv Chen

Ziv has over two decades of experience in the igaming and sports betting industry, having served in senior marketing and business development positions with both B2C and B2B companies, including Playtech and Microgaming. In 2019, Ziv decided to pursue his passion for writing and became a fulltime industry journalist, covering casino, sports, and gambling business news. He’s specialties include casino games and technology, US state gambling regulation, company performance, as well as gambling affiliates and marketing. As a Pitt graduate, Ziv is a diehard fan of all Pittsburgh sports teams, with the Steelers at the top of the list. In his free time, he enjoys reading crime fiction, biographies (mainly of sports personalities, but not only) and American history. Ziv’s Favorite quote: “We're going to pursue perfection, knowing full well we won't catch it, but we're going to relentlessly chase it," Mike Tomlin, Pittsburgh Steelers Head Coach.