Bob Sirott

Founder of PropmtedComms and AI trainer Jason Erkes joins Bob Sirott to talk about how AI can be used to help make dinner reservations and finding restaurant reviews. He also explains the differences of free AI versus having a paid subscription, as well as why banks are attempting to restrict AI access to personal accounts.

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: Fire-Ravaged Palace Grill Could Be Torn Down, Replaced With Residential Building: A developer aims to build a five-story, 24-unit building on the property where the iconic diner stood for more than […]

Cindy Pearlman Gaber, senior writer for the New York Times and entertainment columnist for the Las Vegas Review-Journal, joins Bob Sirott to share details about who could pay the next James Bond, the split of a “Golden Bachelor” couple, and Christmas music from Debbie Gibson. Jason Lesniewicz, senior director of cultural tourism at Choose Chicago, […]

On October 23rd, 2026, Steve Grzanich shares today’s potential market drivers:

Johnny Jet, travel influencer, joins Bob Sirott to talk about the contributing factors of expensive airfare prices and how to use TSA Pre-Check Touchless ID. He also shares details about a new feature on the American Airlines app that automatically looks up the best seat for you, as well as his opinion on using AI as […]

Michael Liptrot, reporter for Block Club Chicago, joins Bob Sirott to share the latest Chicago neighborhood stories. Michael has details on: 5 Things To Know About Garfield Park’s New Quality-Of-Life Plan: The plan lays the groundwork for revitalizing commercial corridors, addressing the food desert and adding jobs with the ultimate goal of increasing life expectancy in […]

President and CEO of the Better Business Bureau Steve Bernas joins Bob Sirott to talk about fake political text messages and the holiday job opportunities that aren’t real. He also shares details about scammers who direct victims to crypto ATMs and debt collection scams that allege you owe money, even if you don’t.

Cindy Pearlman Gaber, senior writer for the New York Times and entertainment columnist for the Las Vegas Review-Journal, joins Bob Sirott to discuss the return of “Glee,” the story about a Chicago bakery coming to Netflix, and Nicholas Cage’s makeover in “Best Pancakes in the Country.” She also shares details about Dwayne Johnson’s latest movie […]

This week on the Associated Bank Thought Leader conversation, Dan Barrins, Senior Vice President in the Commercial Real Estate Group at Associated Bank, joins Steve Grzanich to discuss the latest in Chicago commercial real estate. From a mixed-use acquisition in Libertyville to new developments in Fulton Market, Dan shares what’s driving today’s market and where investors are looking [...

On October 22nd, 2026, Steve Grzanich shares today’s potential market drivers:

NewsNation’s national security contributor Lt. General Richard Newton joins Bob Sirott to talk about the upcoming meeting between President Donald Trump, Russian President Vladimir Putin, and Chinese President Xi Jinping, as well as what they plan to accomplish without Ukrainian President Volodymyr Zelensky. He also shares why Elon Musk called for a restriction of Starshield […]

Dr. Aileen Marty, Infectious Disease Specialist and Professor at Florida International University, joins Bob Sirott to talk about the latest health news. Dr. Marty shares a study that was done concerning water and microplastics, as well as answers a listener question about lung cancer.

Jen Sabella, the Director of Strategy and co-founder of Block Club Chicago, joins Bob Sirott to share the latest Chicago neighborhood stories. She provides details on: Salt Shed Wants To Build 15,000-Person Outdoor Music Venue Next Door: The venue owners filed a zoning request last week to determine the feasibility of turning a nearby industrial lot […]

Karen Conti, Chicago trial attorney, joins Bob Sirott to talk about how could be held liable for the Oregon school shooting and new facts to surface in the O.J. Simpson case. She also discusses a hearing in Supreme Court about making alcohol in a private residence and the case of a stolen flamingo from the […]

Anna Davlantes, WGN Radio’s investigative correspondent, joins Bob Sirott to share what happened this week in Chicago history. Stories include Patrick Kane’s first NHL goal, the city’s first Starbucks, the beginnings of the Curse of the Billy Goat, and more. This Week in Chicago History is sponsored by UI Health.

Cindy Pearlman Gaber, senior writer for the New York Times and entertainment columnist for the Las Vegas Review-Journal, joins Bob Sirott to talk about rumors centered around the 2027 Super Bowl halftime show, the return of Aerosmith, and Catherine Zeta-Jones role in “Kill Jackie.” She also shares details about the posters for Apple TV’s “12 […]

Nationally syndicated financial columnist and author Terry Savage joins Bob Sirott to talk about Medicare Open Enrollment and the differences between all of the plans. She also explains why it’s important to review your coverage every year and who could receive bills for medications. To find help for Medicare plans or ask an agent questions, […]

Social media strategist Scott Kleinberg joins Bob Sirott to discuss why you see contradicting messages on your phone and what they mean, including why storage on your phone is limited even if you pay for extra space. He also explains what happens when you delete photos on one device and it vanishes on all devices, as […]

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: Savannah Bananas Are Coming To Soldier Field Next Year. Here’s How To Get Tickets: After selling out series at Sox Park and Wrigley Field over the past two years, the Bananas […]

Cindy Pearlman Gaber, senior writer for the New York Times and entertainment columnist for the Las Vegas Review-Journal, joins Bob Sirott to share details about Donnie Wahlberg’s private jet accident, new music from The Smashing Pumpkins, and a tour announcement from John Fogerty and Zach Bryan. She also discusses a “Dirty Dancing” sequel, “Cobra Kai” […]

On October 21st, 2026, Steve Grzanich shares today’s potential market drivers:

On October 20th, 2026, Steve Grzanich shares today’s potential market drivers:

Emergency medicine physician and associate chief medical officer for Northwestern Medicine’s Central DuPage Hospital Dr. Jeffrey Bohmer joins Bob Sirott to talk about Pope Leo XIV’s lung cancer diagnosis, typical symptoms, and who should be getting special annual screenings. He also shares details about what role viruses and infections play in a cancer diagnosis and […]

Jon Hansen, host and executive producer of the Block Club Chicago Podcast, joins Bob Sirott to share the latest Chicago neighborhood stories. Jon has details on: Delivery Robots Accused Of Scanning Customers’ Faces, Sharing Biometric Data: Two customers filed separate lawsuits alleging Coco Robotics and Serve Robotics collected their biometric data without their consent as […]

Blockbuster Blake Stubbs joins Bob Sirott to talk about the movies that came out on top at the box office and his review of “Whalefall.” He also discusses who will help resume production for “The Batman: Part II” and if fans of “Ted Lasso” will get another season.