Meet the Season 2 Contestants

Creator and Host of the Talk-Show Experience “Craft Service,” Consultant, Educator, Actress, Full-Time Creative Extraordinaire

West Side

I have lived in Chicago for most of my adult life. So without giving away my age completely, let’s say 15+ years.

The people! The energy of Chicagoans is unmatched!

Pequod’s Pizza. The best there is!

I will meet Oprah! I plan on doing some fabulous collaborative projects with her.

Dance and Fitness Instructor

Streeterville

57 years

The lake

Pizza

Mayor Jane Byrne

Museum Curator, Educator, Musician, Entrepreneur

Bridgeport

Since 1989

The people are amazing!

Pleasant House Pub anything!

Well, I met Robin Williams briefly but I’d have to say Michelle Obama.

Social Sciences Collegiate Divisional Coordinator

Lincoln Park

12.5 years

The world-class architecture and social history

Tavern-style pizza

Roger Ebert

Architectural Historian and Writer

Logan Square

21 years

From our skyscrapers to the vernacular architecture of our neighborhoods, Chicago’s buildings are the best in the universe.

An Italian sub from Bari, taken to go and eaten picnic-style on the concrete barrier blocks next to the Metra tracks on Kinzie.

Da Brat or CupcakKe

Marketing Senior Director, Integrated Marketing and Planning

Bucktown

20-plus years

Never-ending things to do and experience – always something new to check out, regardless of season

Lou Malnati’s pizza

John Hughes

Docent at the Chicago Architecture Center

Downtown

All my life except for a brief sojourn to Miami, Florida

The architecture, the Riverwalk, the lakefront, the water taxi, the bridges, the bridge houses, and Millennium Park concerts.

The caramel cake at Brown Sugar Bakery. Oh, my.

Fannie Barrier Williams

Transportation Librarian

Ravenswood Gardens/Lincoln Square

22 years

I love that there’s always something new to discover. Even after 22 years of living in Chicago, there are streets I haven’t walked down, foods I haven’t tried, people I haven’t met, stories I haven’t heard.

avern-style pizza. John’s on Western is a favorite.

Either Lucy Parsons or my great-great grandmother.

Comedian

I live in Sherman Oaks, CA, but grew up in Harvey.

I lived there 30 years.

Cubs, Bears, Blackhawks, Gibsons Steak House, Tavern on Rush, Carmine’s, and the people of Chicago

Steak at Gibsons

I've met them all.

Content Creator

Lakeview

I was born here and lived here until I was 15 and just recently moved back 2 years ago.

The culture. Chicago just has a different vibe you really can’t get anywhere else.

I love burgers, but the Italian beef combo is top notch!

Barack Obama

Singer and Musician

I’m with my family in “The Pocket” – a small enclave within Humboldt Park

Born here, childhood in Rockford, Hyde Park for graduate school, and then 10 years with my wife. New York City for 12 years and now returned to Chicago.

The lake, the architecture, the history, the music.

Chicago-style polish and regular chips. And a Coke.

Jean Baptiste Point du Sable himself! I’d LOVE to talk about the moment when he said to himself, “Here. This is the place.”

Radio Presenter and Producer; Musical Comedian

West Loop

7 years

The theatre scene. Always something new to discover.

Italian beef

Viola Spolin

Journalist

North Side

52 years

The lake, food, parks, and people

Jibarito sandwich

So hard to say. Jane Addams, Ida B. Wells, Ben Hecht, and my great-grandfather Joe Eng.

Actor

Galena

10 years

Being in a city with such a rich history and beautiful architecture

Deep-dish pizza

Bernie Mac. A true legend.

Journalist

Hyde Park

Since birth

#SummertimeChi on the lakefront

Maxwell Street porkchop sandwich with onions

Mike Royko

Social Justice Artist

Englewood

My entire life

The Black political and organizing culture

Too many to name, but I’ll just say, ALL OUR FOOD IS DELICIOUS!

Fred Hampton

Journalist

West Loop

Since 1994

It's amazing to live so close to world-class food, architecture, and art.

Thin-crust pizza from Pizza, Fried Chicken, Ice Cream

Walter Payton

TV Journalist and Documentary Producer

Lincoln Park

More than 50 years

Its sprawling big-city cultural vitality and sophistication mixed with small-neighborhood openness and diversity.

Chicago-style hot dog

Carl Sandburg

Performer and Teaching Artist

The Loop

Born and raised

The art and culture of the city. From live shows to just looking up at skyscrapers, there’s a lot to look at in this city!

Anything from Portillo’s

Tomi Adeyemi, author of Children of Blood and Bone

Writer and Performer

I used to live in Lincoln Park before moving to L.A.

About 15 years

Great place to do theater and starve while also having an ample supply of tomato and deep-dish crust that can be injected right into the bloodstream

A Midnight Diner omelette after performing in an underground bar for an audience of one. Well, two, if you count the bartender.

Orson Welles so I can ask him about his classic work: commercials for French champagne and frozen peas. Oh, and also the afterlife.

Leasing Director

Logan Square

My entire life.

Walking the dog (Elvis) along the lakefront!

Chicago-style hot dog

Harry Caray

Actor, Writer, Creator, Producer, Director

Oak Park

Since 2014

The authenticity of the people and strong sense of community. I also love Lake Michigan!

Mexican tortas in Pilsen!

Oprah!

Reporter

Hyde Park

I’m a Chicago native.

The people

Harold’s Fried Chicken

Gwendolyn Brooks

Comedy and Theater Producer

Lakeview/Logan Square

56 years

The diversity

Jimmy’s Polish

Mike Royko

Actress, Yoga Teacher, and Special Projects Coordinator

Uptown

Since 1994

The vibe, the people who create that vibe, the lake, the parks

Korean!

Does Abe Lincoln count? The Obamas. Oprah.

Radio and TV Host

I grew up on the North Side and now live in East Garfield Park.

Luckily, my whole life!

Being influenced by so many different cultures.

Jibarito from Papa’s Cache

Mayor Harold Washington

CEO of the American Red Cross

North Side

26 years

Chicago summers, the lakefront, the festivals, and the music

Pizza – tavern-style or deep-dish

Barack Obama

Public Relations, President of Rudd Resources LLC

South Side

37 years

The city’s diversity, vibrancy, and livability

Pizza

Chaka Kahn or Ida B. Wells-Barnett

Journalist, Broadcaster, Author

Darn, we do not currently live in Chicago.

The worst thing about currently not living in Chicago is not living in Chicago!

The worst thing about currently not living in Chicago is not living in Chicago!

Anything by any member of the Bayless family.

Ida B. Wells

Art Director and Graphic Designer

Chicago Lawn/Gage Park

My whole life

The skyline and lakefront is by far one of the best things about Chicago. But also the mix of culture, arts, and architecture is wonderful (so much Art Deco!)…and the FOOD!

Ooo! Hard one! I’m kind of a foodie. I love a good hot dog! (I miss Hot Doug’s and the Vienna spot.) But I also love a good Italian beef and deep-dish pizza! I guess different stages in my life marked a different favorite. As a child, Twinkies and Ding-Dongs occupied my mind. In my twenties, it was pizza puffs (the food of late-night champions). In my thirties, I discovered restaurants and flaming saganaki! I can’t choose! I love it all!

Thanks to your show, I already had the privilege of meeting Kurt Elling and Geoffrey Baer. So perhaps Jerry Reinsdorf or Studs Terkel.

Visual Artist

Hyde Park

My entire life and 33 years in Hyde Park

We have everything you need here: the best art, best architecture, the realest people, and the best summer experience.

If we’re talking classic Chicago, I’ll have to give a shoutout to Lawrence Fishery and its fried jumbo shrimp.

Hands down, the late, great Bernie Mac

Entertainment Reporter

Ravenswood

Since 2016

The ease of transport. Growing up in rural North Carolina and having to drive a car to get truly anywhere, it’s such a relief to be able to take a train or bus to practically all points of the city. Also, the city as a whole is one of the most convivial places I’ve ever been. Summer or winter, people tend to be upbeat and joyful – and in the winter, we certainly need it!

My favorite restaurant (at the moment, anyway!) is a Japanese restaurant called Rolls N Bowls. It’s on Lincoln Avenue, just behind the Western Brown Line stop. I could live on their steak teriyaki; to be honest, I practically do.

I would love to meet Viola Spolin, the mother of improv theatre. I moved to Chicago specifically for its comedy and theatre scene, and before I did anything else, I devoured her Improvisation for the Theater. I’d love to know her thoughts on where the form has gone and what she would do to improve it, make it more specific, and help it reach a broader audience. I’d also love to meet Charles Yerkes, who more or less singlehandedly strong-armed the elevated Loop into being built downtown. A guy with that much force of will could certainly offer some interesting life advice (though I imagine one of his tips would likely be, “If you can’t bribe ’em, threaten ’em” – a bit of advice I’d probably discard).

Journalist

Wicker Park

Five years in Chicago proper, but a lifelong wannabe (suburbanite)

The friendly people! The food! The lakefront! The seasons! The stories to cover! Did I mention the food? Oh, and Chicago's awesome PBS station, WTTW!

All of it, especially cocoa from Katherine Anne Confections, egg rolls from Shanghai Inn in Lincoln Square, an old-school pizza puff, and of course, a Chicago-style hot dog (pile on extra sport peppers and mustard, please). A shot of Malört after that meal, for good measure.

Ida B. Wells – what a fighter and an inspiration! Also wish I could go back in time and score an invite from “Hinky Dink” Kenna and “Bathhouse John” Coughlin to their famous (infamous?) First Ward Ball. Imagine I’d have a story or twenty to cover after talking with them.

Executive Producer

River Forest

My whole life

Lake Michigan

Anything Italian

Harrison Ford would be cool.

Digital Reporter with WTTW News, on the nature and environment beat

Lincoln Square

Closing in on 30 years

I love being able to walk everywhere, whether it’s to Walgreens or the grocery store or a movie theater or a park.

Scooter’s Frozen Custard. Their whiskey caramel flavor is... chef’s kiss.

Oooh, that's a tough one. To be honest, I kind of don’t like to meet famous people. One of the things that I enjoy most about my job is getting to meet regular Chicagoans, who are quite extraordinary and inspiring in their own way and usually they don't even realize it. Kind of a cop-out answer, but it’s the truth.