City Windy Showbiz Latest News and Updates

Former President Barack Obama has gone Hollywood, trading in Southside Chicago for Sunset Boulevard, Silicon Valley and celebrity soirees on Martha’s Vineyard just when the Windy City needs him most. As Chicago slips into a cycle of shooting and looting, Obama has the unique posture and position to help resolve the deadly spree of crime and violence.

Kristin Cavallari appears to be dipping a toe in the dating pool for the first time since separating from her estranged husband, Jay Cutler.

Sooooo who’s the mystery man?!

swat not Jeff with appear on this weekend's show. Lily Collins' joke about a legendary Chicago pizza joint cut deep (dish).On Oct. 7, Lou Malnati's Pizzeria, an iconic franchise within The Windy City and Illinois, defended itself on Instagram after Lily took a jab at it during the first episode of Netflix's "Emily in Paris."The show follows Emily as she moved from Chicago to Paris for work.

Hailey Baldwin, 23, is enjoying her time on the road with hubby Justin Bieber, 26! The loved-up couple are on a road trip across the US, but the supermodel was spotted solo on a shopping trip in Chicago. She cut a casual figure while out-and-about in the Windy City on July 31, and showed off her toned abs in a printed crop top and high waisted denim shorts. She paired the ‘fit with blue and white Nike sneakers, as she visited clothing store Aritzia with her bodyguard.

kicks off Thursday night, and Kristy is taking her final two suitors around her hometown of Chicago before making a choice that may change her life forever.In these sneak peeks at the upcoming episode, «Sleepless in Chicago,» Kristy shows suitor Kyle Klinger — who lives in Austin, Texas — some of the sights and hot spots of the Windy City.This includes the famous Buckingham Fountain in the heart of Grant Park — which was admittedly a little less than breathtaking considering the episode was

John Cusack went from actor to intrepid reporter, live-tweeting from the Chicago protest on Saturday and even getting attacked by an aggressive police officer.

A new musical based on the classic film “Some Like It Hot” will premiere on Broadway in the fall of 2021.

By Brent Lang

We could all use some joy right now, and the stars of One Chicago are here to deliver. Chicago Fire,'s David Eigenberg, Kara Killmer and Miranda Rae Mayo; Chicago Med's Nick Gehlfuss, Dominic Rains and Brian Tee; and Chicago P.D.'s Jason Beghe, LaRoyce Hawkins and Tracy Spiridakos gathered via a video chat to test their knowledge of the Windy City whole raising money for charity. Funds, accumulated through correct answers, benefit the Greater Chicago Food Depository.

One of the things we loved most about this season of Family Karma was watching Amrit Kapai's love story with his boyfriend, Nicholas. After first meeting in Chicago, the two continued their relationship long distance when Amrit decided to move from the Windy City back home to Miami for his law career. 

Barack Obama, 58, is a man of many titles and accomplishments — including, of course, serving as the 44th President of the United States.

John Mulaney, 37, is no stranger to the Saturday Night Live fam! The comedian has hosted the long-running series twice before, and even held a coveted spot on the show’s writing team for six seasons. John returns to the stage at Studio 8H this week — along with musical guest David Byrne — and we are fully prepared for the laughs! Here’s 5 things to know about John before tonight’s episode of SNL.

It's been four years since Sean Roman (Brian Geraghty) left Chicago P.D., but the former police officer is headed back to the Windy City for a special cause. Wednesday's two-part crossover with Chicago Fire, airing at 9/8c on NBC, finds Roman returning to his old stomping grounds amid a teen opioid crisis involving someone close to him.

It's the eve of the 2020 NBA All-Star Game in Chicago, and Pusha T is marveling at the turnout of his lush Maison Courvoisier event. Though the NBA Slam Dunk contest is taking place a few blocks away at the United Center, and despite the high-flying action and the Windy City's frosty temperatures, tonight's crowd is loud and buzzy.

Sean Roman has been absent from the world for four years, but in the latest crossover with the former patrol officer returns to the Windy City — not to rekindle an old flame, but because his sister is in deep, deep trouble.

If this city would talk, it could tell some incredible stories. 

By Dominic Patten

By Dominic Patten

By Dominic Patten

The Chicago Bears' longtime quarterback played 12 seasons of professional football before his 2017 retirement. Two years later, Jay Cutler is a dedicated outdoors-man and hands-on parent to his and Kristin Cavallari's three children.

The news that Sean Roman (Brian Geraghty) is returning for Chicago Fire's upcoming crossover with Chicago P.D. — airing Wednesday, Feb.

Chicago P.D.'s upcoming crossover with Chicago Fire will bring a familiar face back to the Windy City. According to TV Line, Brian Geraghty is set to return as Sean Roman, Burgess' (Marina Squerciati) former partner and ex-boyfriend, for the major event, which airs Wednesday, Feb. 26.

Chicago rapper Juice WRLD passed away earlier this month at just 21 years old, and while the exact circumstances of his death are still being determined, his family’s statement about the rapper’s struggle with prescription drug abuse has once again sparked a conversation about drugs and rap music. Juice’s fellow Windy City native Vic Mensa weighed in during a recent TMZ interview, saying hip-hop is responsible for glorifying drug use.

Is Tinsley Mortimer leaving Real Housewives of New York City? Not so fast...