COLLABORATION SIGNIFIES MEANINGFUL SUPPORT FOR WOMEN’S SPORTS

CHICAGO (June 4, 2026) — The Chicago Sky today announced a multi-year agreement with Progressive Insurance®, the largest deal in Chicago Sky history.

“The Sky organization is thrilled to announce a significant agreement with Progressive, whose investment displays a strong commitment to women’s sports,” Sky Vice President of Corporate Partnerships Alex Teodosi said. “Progressive is making its presence felt in grassroots Chicago communities, and our collaboration will allow us to build on that momentum right in our backyard.”

Progressive will join forces with the Chicago Sky Foundation to be the Presenting Partner of our reading literacy program. The initiative aims to expand access to high-quality reading intervention by providing specialized literacy training for Chicago Public School educators.

“Progressive is proud to partner with the Chicago Sky, an organization that continues to lead through both athletic excellence and meaningful community impact,” said Sean Freeman, Progressive Media Business Leader. “Women’s sports are experiencing incredible momentum, and we’re excited to support a league and team that are inspiring fans, elevating female athletes, and creating powerful connections within their communities. We’re thrilled to work alongside Chicago Sky to make meaningful impact both on and off the court.”

Additionally, Progressive will be featured in prominent on-court assets, including seeing its logo inside the free-throw circle and baseline positions. The agreement extends to Sky digital channels across through content & storytelling. Progressive will also be the Presenting Partner of the Sky’s newest hype group, the Sky Lights, to keep fans energized all season long.

About Chicago Sky

The 2021 WNBA Champion Chicago Sky are a professional women’s basketball team founded in 2005 by principal owner, Michael Alter. The Chicago Sky were the first independently owned women’s professional basketball team to join the WNBA and play at the Wintrust Arena. The WNBA regular season runs from May-September. Follow @chicagosky and tag #WNBAAllStar2026 and #NeverOutdoneChi on Facebook, Instagram, LinkedIn, TikTok, and X. Call 866.SKY.WNBA or visit sky.wnba.com for more information.

About Progressive

Progressive Insurance^® makes it easy to understand, buy and use car insurance, home insurance, and other protection needs. Progressive offers choices so consumers can reach us however it's most convenient for them — online at progressive.com, by phone at 1-800-PROGRESSIVE, via the Progressive mobile app, or in-person with a local agent.

Progressive provides insurance for personal and commercial autos and trucks, motorcycles, boats, recreational vehicles, and homes; it is the second largest personal auto insurer in the country, a leading seller of commercial auto, motorcycle, and boat insurance, and one of the top 15 homeowners insurance carriers.

Founded in 1937, Progressive continues its long history of offering shopping tools and services that save customers time and money, like Name Your Price^®, Snapshot^®, and HomeQuote Explorer^®.The Common Shares of The Progressive Corporation, the Mayfield Village, Ohio-based holding company, trade publicly at NYSE: PGR.