Jay’s Chicago returns for a fifth season on WTTW

Jay Shefsky

Chicago is full of creative and passionate people. On JAY’S CHICAGO, Jay Shefsky introduces us to some fascinating people who live and work in Chicago.

Returning for a fifth season on Thursday, March 24 at 8:30 pm on all WTTW platforms, JAY’S CHICAGO shines a spotlight on ordinary people who do extraordinary things – from pursuing unusual passions, to finding innovative ways to meet daunting challenges, to practicing unique art forms. 

“Growing up in Chicago, one of my heroes was Studs Terkel,” Jay Shefsky said. “He understood that everyone has a story to tell – and that if you listen with respect, people who aren’t experts or celebrities may have the most to teach us. One of the great joys of my career has been getting to know the people in these stories, and sharing them.” 

“We are excited to premiere a new season of JAY’S CHICAGO, filled with stories – told as only Jay can – that exemplify the creativity, curiosity, and resilience of the people who live and work in our city,” said Lisa Tipton, Head of Programming at WTTW. “As a public media organization, our purpose is to enrich lives, engage communities, and inspire exploration, and these slices of life deliver on that purpose.” 

On the companion website wttw.com/jayschicago, watch episodes of the series going back to the beginning. 

Television Schedule: 

JAY’S CHICAGO will also be streaming on wttw.com beginning March 24. 

March 24, 8:30 pm 

Out in Nature 

Jay is out in nature – tagging along with a record-breaking teen birder, helping with a controlled fire that rejuvenates a forest, and learning where to see the area’s best wildflowers. He also makes friends with an unnervingly large insect. 

March 31, 8:30 pm 

Song and Dance 

Jay is entranced by a 102-year-old former nightclub performer, gets to know Bob Fosse’s childhood dance partner, and hears the inspiring story of local blues pianist Erwin Helfer’s COVID-era recovery from serious depression with the help of friends. And a Chicago guitar virtuoso takes on the Beatles. 

April 7, 8:30 pm 

Life Stories 

Jay explores a mystery: who is that little girl in dozens of century-old negatives found in a Chicago attic? Then, a handmade “onesie” becomes a treasured symbol of family love as it is shared by dozens of babies across generations of a single family (cuteness warning!). And he meets the undocumented immigrant who became Chicago’s winningest storyteller. 

WTTW | Jay’s Chicago | Release | page 2 of 3 

April 14, 8:30 pm 

Mentors Changing Lives 

Jay is on the hunt for great mentors. A dynamic Chicago singer was once bullied for losing her hair; now she inspires young girls with the same condition. The Black Fire Brigade gives a boost to young paramedics, EMTs, and firefighters. A Chicago dance legend teaches teens – how did his inspiration come from a TV clown? And a South side wrestling coach says his life was saved by his own high school coach; now he pays it forward. 

April 21, 8:30 pm 

Good Deed Doers 

Jay meets local world-changers. A local pilot creates an aviation program in a Chicago high school, inspired by great Black fliers. A group home worker exposed to COVID quarantines with her residents to continue caring for them. A young nun gives up Olympic dreams, but still uses running to support her West side community. A volunteer army of 3D printer owners makes thousands of face shields. And a cancer diagnosis inspires a rare book collector to donate his valuable collection to a local university. 

April 28, 8:30 pm 

Cool Stuff Makers Jay loves to meet people who make things: a retired woman whose basement is overflowing with a lifetime of fabulous miniature creations, and a maker of handmade hats and gloves that can only be called works of art. He visits an internationally renowned violin-making school in a Chicago suburb, and the first vinyl record maker in Chicago in 30 years. And Jay gets a lesson from a young artist who creates taxidermy like you have never seen. 

May 5, 8:30 pm 

The Stories Photos Tell Jay meets photographers with stories to tell. When one Chicago photographer was young, his epic cross-country adventure to meet railroad tramps yielded great stories and stunning photos. Another photographer left behind half a million images – including intimate scenes of Black Chicago – now, his daughters want to share them with the world. He explores River North’s much grittier past, through the lens of legendary photographer Tom Palazzolo. And he introduces us to a local couple who spent years capturing breathtaking images of the world’s great hikes; grounded by COVID, they took a closer look at what Chicago has to offer. 


JAY’S CHICAGO is written, produced, and edited by Jay Shefsky. VP, Original Content Production: Geoffrey Baer. Series Producer: Daniel Andries. Principal Photography: Felix Mendez. Additional Photography: Grant Banks, Tim Boyd, Steve Eisen, and Tom Siegel. Audio Mixing and Final Post-Production: Michael S. Sweeney. Post-Production Supervisor: Mark Anderson. Production Assistant: Alexandria Martin. Art Direction: Linda Fox, Reed Marvine. Website Development: Kevin Crowley. SVP Marketing and Digital: Anne Gleason. 


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