Chi-lebrity check-in: People who make Chicago, Chicago

Chicago has never been short on personality. We are a city built on bold ideas, broad shoulders, late nights, early mornings and people who walk into a room and instantly shift the energy. From the moment I moved to Chicago, I’ve been quietly (and joyfully) collecting those people. The storytellers, the culture-makers, the do-gooders, the entertainers, the dreamers… the ones who are woven into the very fabric of this city.

So, consider this a love letter to a few of my favorite Chi-lebrities—not famous because they chased the spotlight, but because they became it. I asked each of them three simple questions: What was your highlight of 2025? What are you looking forward to in 2026? And what is your wish for Chicago in the year ahead?

Their answers are funny, moving, hopeful, heartfelt and unmistakably Chicago.

📚 Donna La Pietra & Bill Kurtis

Authors, journalists, media icons, philanthropists—and yes, “Anchorman” legend

2025 Highlight:

The publication of Bill Kurtis’ memoir, WHIRLWIND, proved to be far more emotional than either expected. Revisiting the “eras” of a life—set against sweeping historical moments—became an exercise in reflection, gratitude, and deep connection. Even more unexpectedly, it reopened doors to friendships and memories spanning decades.

Looking Ahead to 2026:

Another book! A follow-up filled with stories that didn’t quite make the final cut of WHIRLWIND. Writing is already underway.

Wish for Chicago:

A city that continues to nurture original artistic vision, big dreams, and—always—kindness.

🏛️ Maria Pappas

Cook County Treasurer, mayoral hopeful

2025 Highlight:
Attending the consecration of the largest Eastern Orthodox Church in the world in Bucharest, Romania—a moment rich with history, faith and global significance.

Looking Ahead to 2026:
Pushing forward tax sale reform legislation in Springfield, continuing my long-standing work to bring fairness, transparency and accountability to government.

Wish for Chicago:
Short, bold, and unmistakably on-brand: Pappas for Mayor!

 🩰 Greg Cameron

President & CEO, The Joffrey Ballet

2025 Highlight:

A year defined by travel—London, Tuscany, Rome, Madrid, Fire Island—and always the joy of returning to Sweet Home Chicago.

Looking Ahead to 2026:

The Joffrey Ballet’s 70th anniversary. A milestone year filled with curiosity, collaboration, community, kindness, and (of course) dancing. Don’t miss AMERICAN ICONS this February.

Wish for Chicago:

Put creativity at the heart of the city’s future. Through initiatives like the Cultural Stadium, downtown can be a place where everyone feels welcome and inspired.

🎤 John St. Augustine

Award-winning media host, author, motivational speaker, producer

2025 Highlight:

World travel and literary success were wonderful—but nothing topped welcoming my third granddaughter, Ella, just before Christmas.

Looking Ahead to 2026:

A fall trip to Egypt. Mystery, magic and millennia of stories await.

Wish for Chicago:

That we lean into our better angels, honor our diverse history, build a compassionate future—and maybe show a little more patience during rush hour.

🍷 Alpana Singh

Restaurateur, retired master sommelier, television favorite

2025 Highlight:

A guest appearance on Season 4 of The Bear. Filming in my restaurant felt surreal—and deeply meaningful—as the show continues to serve as a love letter to Chicago’s food scene.

Looking Ahead to 2026:

Turning 50 with excitement, clarity, and purpose. And I'm just getting started—and am personally campaigning for a “40 Over 40” award.

Wish for Chicago:

A Bears Super Bowl run (carefully whispered to avoid a jinx) and a surge of civic pride after a challenging year.

🍝 Israel Idonije

Former Chicago Bear, restaurateur, entrepreneur

2025 Highlight:

Opening Buttercup, a retro Italian bar and café that represents the future vision of Pangea Restaurant Group.

Looking Ahead to 2026:

New restaurant concepts, karaoke and live music, ice cream, Hyrox competitions and several projects still under wraps.

Wish for Chicago:

Keep the Chicago Bears in the city. Period.

⚖️ Richard Boykin

Attorney, philanthropist, 7^th Congressional District candidate

2025 Highlight:

Watching my son complete his first year of college at the University of Iowa.

Looking Ahead to 2026:

Winning election to represent Illinois’ 7th Congressional District.

Wish for Chicago:

Unity around closing the achievement gap in reading, math and science.

🎨🍝 Thomas O’Gorman

Author, social columnist, painter, gourmet cook

2025 Highlights:

A memorable lunch with Salvatore Ferragamo at Piccolo Sogno. Rediscovering La Scarola. And, with deep sadness, the loss of my beloved travel companion of 25 years, Rose Marie O’Neill.

Looking Ahead to 2026:

Fifty pounds lost, two new books, a New York painting exhibit—and renewed energy.

Wish for Chicago:

Leadership that restores civility and transforms the city.

🛒🍴 Amanda Puck

Roundy’s & Mariano’s Divisions VP of Communications and Brand Development; foodie, philanthropist

2025 Highlight:

Watching Chicago shine brighter than ever—through unforgettable culinary moments, meaningful community wins, and the city’s continued celebration of creativity. For me, it was a powerful reminder of why I love what I do. And let’s be honest: Chicago Gourmet once again delivered bites I'm still dreaming about.

Looking Ahead to 2026:

More incredible flavors, unforgettable experiences and opportunities to connect people through food and storytelling. For me, 2026 feels like a year made for bold ideas and big bites.

Wish for Chicago:

That the city continues to innovate while staying true to its roots—celebrating diversity, uplifting local talent and cementing Chicago as the ultimate destination for food lovers everywhere. And yes… a Bears Super Bowl win wouldn’t hurt either.

🍽️ Chef Art Smith

Restaurateur, philanthropist, author, TV personality, chef

2025 Highlight:

Being named the first American Chef Partner of Borgo Laudato Sì by the Vatican—and serving “holy biscuits” to Chicago-born Pope Leo XIV. Also: losing 55 pounds and reclaiming his health.

Looking Ahead to 2026:

Living in Castel Gandolfo, opening the property’s first restaurant in 425 years, writing a new book and teaching children to cook.

Wish for Chicago:

A renewed spirit of helping, sharing and expanding our sense of family. Chicago made me—now it’s time to keep paying it forward.

🎬 Michael Kutza

Founder Chicago International Film Festival, movie critic, author, podcast host

2025 Highlight:

Time spent with the Chaplin family in Vevey, Switzerland—home of chocolate and Charlie Chaplin.

Looking Ahead to 2026:

Turning my book STARSTRUCK into a documentary film.

Wish for Chicago:

A city that finally gets serious about addressing crime and violence.

🎙️ Lisa Fielding

WBBM NewsRadio anchor/reporter

2025 Highlights:

My parents’ 60th anniversary, a high school reunion, a birthday in the Bahamas and covering the James Beard Awards.

Looking Ahead to 2026:

More travel, more adventure, more quality time.

Wish for Chicago:

More peace, less violence and more positive stories worth telling.

🏡 Cortney Hall

Emmy-nominated "NBC Chicago Today" host and creator "Open House Chicago"

2025 Highlight:

Launching Open House Chicago, a first-of-its-kind luxury real estate show—two seasons, a holiday special and an Emmy nomination.

Looking Ahead to 2026:

Continued growth and expansion of the series.

Wish for Chicago:

Peace and economic growth citywide.

🌞 Matt Rodrigues

Emmy-winning "NBC Chicago Today" host and creator "Matt in the Morning" 

2025 Highlights:

Season seven of Chicago Today, a second Emmy win, GLAAD nominations, and the growth of Matt in the Morning.

Looking Ahead to 2026:

More of everything—and maybe a vacation in New Zealand.

Wish for Chicago:

That the world finally sees what we already know: Chicago is full of joy—and that should be the headline.

Final Thought:

These Chi-lebrities remind us that Chicago’s greatest asset isn’t its skyline, architecture or even its food (though we do love all three). It’s the people—dreaming, building, creating, loving and hoping for something better. And if their wishes come true, 2026 is going to be one remarkable year.