Dean Richards, entertainment reporter for WGN, joins Bob Sirott to provide the latest news in entertainment. Bob and Dean talk about Sean “Diddy” Combs’ upcoming sentencing and Taylor Swift’s new album. They also share details about things to do this weekend and Dean’s review of “The Smashing Machine.”

The Chicago Cubs defeated the San Diego Padres 3-1 in their winner-take-all Wild Card series finale. It’s the first time the team has won a postseason series since 2017. Chicago Tribune columnist Paul Sullivan joins Bob Sirott and Andy Masur to recap the critical moments and look ahead to the divisional series against the Milwaukee Brewers.

Sam Toia, President of the Illinois Restaurant Association, joins Bob Sirott to talk about when Chicago restaurants have to pack up their outdoor seating situated on sidewalks and some of his favorite restaurants patios. He also discusses a three percent surcharge that could be removed from your dining bill, how important restaurant reviews are for businesses, and robot deliveries coming to DoorDash.

Shamus Toomey, Editor in Chief and co-founder of Block Club Chicago, joins Bob Sirott to share the latest Chicago neighborhood stories. Shamus has details on:

City Stops Damen Silos Demolition Due To Excessive Dust: The demolition is on hold until the city approves new plans, officials said. Neighbors and environmental leaders had previously called for the city to stop the demolition over dust worries after the botched Hilco implosion in Little Village in 2020.

Humboldt Park Boathouse Could Get All-Day Cafe — With Beer Garden: The team behind the North Pond restaurant in Lincoln Park have proposed opening Cafe Valera at the Humboldt Park Boathouse.

Vacant Chinatown Lot Could Become Riverfront Office Complex With Restaurant: The city selected a proposal from developer Mao S. Mei to turn a 0.95-acre city lot into a riverfront commercial complex with a restaurant and riverfront space.

Marianne Murciano, Bob Sirott’s wife and founder of Savvy-Planet, joins Bob to talk about how games can bring your party to life by engaging people. Some of Marianne’s favorite party games include Two Truths and a Lie and Telephone Pictionary.

On October 3rd, 2025, Dave Schwan, in for Steve Grzanich, shares today’s potential market drivers:

The Cubs and San Diego Padres are tied at a game apiece in their best-of-three Wild Card playoff series. The winner of this afternoon’s game will advance to the next round to take on the Milwaukee Brewers. Former Chicago Cubs center fielder Bob Dernier joins Bob Sirott and Andy Masur to share memories of when he and his teammates took on the Padres in the 1984 playoffs. He also talks about the keys to winning today’s game and remembers his teammate, the late Ryne Sandberg.

Columnist and film critic Richard Roeper joins Bob Sirott to talk about the Cubs’ three afternoon games and how people seem to prefer the earlier start time. They also discuss the history of the AOL dial-up service and why it was recently discontinued.

VP of Public and Board Relations of the BBB Tom Johnson joins Bob Sirott to talk about common moving scams, being cautious when shopping online, and what to know for October’s Cybersecurity Awareness Month. He also shares details about a scam that involves calling someone back, fake recovery emails associated with your Gmail account, and why it’s important to keep your cell phone number private.

Dean Richards, entertainment reporter for WGN, joins Bob Sirott to provide the latest news in entertainment. Bob and Dean share details about an “Everybody Loves Raymond” reunion, talk of a possible *NSYNC reunion, and the return of “Reading Rainbow.” They also talk about Bad Bunny hosting SNL, the reunion of Paris and Janet Jackson, and Dean’s interview with Emma Thompson.