Richard Roeper joins as a guest co-host on ‘Windy City Weekend’ while Art ‘Chat Daddy’ Sims talks about an upcoming fundraiser

CHICAGO (WLS) — On “Windy City Weekend” Friday, Richard Roeper filled in as guest co-host.

Art “Chat Daddy” Sims recently appeared on Host Chat to discuss an upcoming fundraising event for Guest House Chicago. This local nonprofit offers affordable temporary lodging to medical patients needing to stay close to major hospitals in Chicago. The fundraising event, The House Always Wins 2025, will be held at Carnivale Restaurant on April 28. Attendees are encouraged to dress festively for this highly anticipated annual fundraiser. VIP ticket holders will have exclusive access to the VIP lounge with special tastings and cuisine. The main event will run from 6 to 9:30 pm, and valet parking will be available.

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For tickets and more info, visit www.guesthousechicago.org.

Ari Siegel, an entrepreneur from Northbrook, shared his journey on “Shark Tank” with his business, History By Mail. Siegel discussed how he founded the business, prepared to pitch to the millionaire investors on the show, and surprised the audience with a giveaway. History By Mail offers a subscription service providing replicas of engaging historical documents from American history. These replicas, designed by a team of graphic artists, are delivered to subscribers on high-quality paper accompanied by a contextual document.

Receive 15% off on HistoryByMail.com by using promo code: SHARKTANK.

The “Windy City Bite Bracket,” a tournament featuring 32 Chicago restaurants, took place last month. The competition used an elimination-style format, and the winner, or the “chomp-ion,” has been announced. Sean Asbra, the general manager of Pequod’s, visited to discuss their victory as having the best bite in Chicago and had a surprise for the audience.

For more on Pequod’s, visit https://pequodspizza.com.

Film critic Richard Roeper reviewed new movies and shows hitting theaters and streaming platforms this weekend.

‘The Friend’ – SPEND
Naomi Watts and Bill Murray star in this drama about love, friendship, grief and healing.

‘Eric LaRue’ – SPEND
Michael Shannon makes his directorial debut in this heavy drama starring Judy Greer. She plays a mother preparing to visit her son, a high school murderer, in prison.

‘Dying for Sex’ – SPEND
Michelle Williams stars in this limited FX series based on a true story. She stars as a woman who decides to explore her sexuality after being diagnosed with stage 4 cancer.