Bob Sirott

Founder of PromptedComms 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 85 years.

Foundry Park Breaks Ground After Years Of Uncertainty At Former Lincoln Yards Site: The long-stalled megadevelopment will bring thousands of homes, parks and a riverwalk to the sprawling property, once home to A. Finkl & Sons steel company.

CTA To Close Loop ‘L’ Tracks This Weekend For Repairs: Brown, Green, Orange and Pink line trains will be affected by the closure between 4 a.m. Saturday and 4 a.m. Monday.

Sponsored by Great Lakes Credit Union – Committed to financially empowering local communities. For more info go to GLCU.org.

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, also joins Bob to talk about the Halloween-themed events happening this weekend, including, Arts in the Dark, Zoo Brews: Howls and Growls, Fright at the Field, and more.

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 a travel agent.

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 the neighborhood.

Mexican Mr. Beef? Stand That Inspired ‘The Bear’ Hosts Pop-Up With Michelin Chef: Acclaimed London chef Santiago Lastra is partnering with the River North beef stand, “The Bear” crew and actor Will Poulter for Sunday’s event featuring a spin on Italian beef, made with beef tongue.

20 Ways To Celebrate Día De Los Muertos In Chicago: Ofrendas, Festivals And More: From art exhibits and theater to bar crawls and parties, here are various ways to celebrate the Day of the Dead in Chicago this month.

Sponsored by Great Lakes Credit Union – Committed to financially empowering local communities. For more info go to GLCU.org.

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 role, the return of “The Holiday” to theaters, and new music from Blondie.

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 next.

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