In this episode, Fran Spielman interviews Cristina Pacione-Zayas, former Illinois lawmaker and the current Chief of Staff to Chicago Mayor Brandon Johnson. Pacione-Zayas discusses the challenges and pressures of her role, focusing on key city issues such as affordability, safety, and infrastructure. The conversation also touches on the political tensions surrounding Mayor Johnson's administration, including budget disputes with the City Council and efforts to hold ICE agents accountable for their actions.

Fran Spielman hosts a conversation with Kristen Reynolds and Guy Chipparoni, the President & CEO, and Chairman of the Board of Choose Chicago, respectively. The discussion covers the financial challenges Chicago faces in competing with cities like Las Vegas and Orlando for conventions and tourism. Reynolds and Chipparoni emphasize the importance of marketing Chicago as a destination, regardless of season, highlighting winter activities, restaurant and theater weeks, and the potential of future significant events like the opening of the Obama Presidential Center.

Fran Spielman is joined by former Sun-Times sports columnist Rick Telander and sports stadium consultant Marc Ganis to analyze the Bears' gripping Wild Card victory against the Green Bay Packers, driven by the late-game heroics of quarterback Caleb Williams and wide receiver DJ Moore. The trio also examines the potential long-term impact of Bears' newfound success on their plans for a new stadium, debating whether it will be built in Arlington Heights, Illinois, or possibly Northwest Indiana.