Bob Sirott

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 […]

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 […]

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 second baseman, Bob Dernier, joins Bob Sirott and Andy Masur to shares memories of when […]

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 […]

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 […]

Stephanie Lulay, Executive editor and Co-Founder of Block Club Chicago, joins Bob Sirott to share the latest Chicago neighborhood stories. She provides details on: The Chicago Art Locker Brings Whimsy And Free Works Of Art To Avondale: What started as a free initiative has blossomed to include art supplies, bilingual Know Your Rights pamphlets and stickers. […]

Duston Detrick, Vice President and Business Banking Relationship Manager at Associated Bank, joins Steve Grzanich on this week’s Thought Leader conversation to discuss the current state of the economy in the midst of a government shutdown, and what it could impact, including the jobs report and small business.

On October 2nd, 2025, Dave Schwan, in for Steve Grzanich, shares today’s potential market drivers:

Dr. Aileen Marty, Infectious Disease Specialist and Professor at Florida International University, joins Bob Sirott to talk about the latest health news. Dr. Marty discusses a study concerning children who contract COVID multiple times.

The Cubs beat the San Diego Padres 3-1 in Game One of their best-of-three Wild Card series. Seiya Suzuki and Carson Kelly’s back-to-back home runs in the fifth inning ended up being all the team needed to put the Padres against the brink of elimination. Chicago Tribune columnist Paul Sullivan joins Bob Sirott and Andy Masur […]

Anna Davlantes, WGN Radio’s investigative correspondent, joins Bob Sirott to share what happened this week in Chicago history. Stories include the closing of Riverview Amusement Park, the Cubs’ pennant win of 1945, the birth of the Sarah Lee Bakery, and more.

Karen Conti, Chicago trial attorney, joins Bob Sirott to talk about a lawsuit against ICE that accuses them of making allegedly false arrests and what a court could do if they violated the law. She also shares details about who former FBI director James Comey will be represented by and what the judge will take […]

Dean Richards, entertainment reporter for WGN, joins Bob Sirott to provide the latest news in entertainment. Bob and Dean talk about more details that are being revealed about the divorce of Nicole Kidman and Keith Urban, as well as Jimmy Kimmel on Stephen Colbert’s show and the comedians under fire for performing at a Middle […]

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: Sculpture Walk Connecting Jefferson And Portage Park To Be Unveiled This Weekend: The NW Side Art Walk features 10 sculptures along the Milwaukee Avenue corridor, five of them new. A dedication […]

On October 1st, 2025, Dave Schwan, in for Steve Grzanich, shares today’s potential market drivers: