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Meet the Season 2 Contestants

Jenna Anast
Occupation
Creator and Host of the Talk-Show Experience “Craft Service,” Consultant, Educator, Actress, Full-Time Creative Extraordinaire
Neighborhood, Town or Suburb
West Side
How long have you lived in Chicago?
I have lived in Chicago for most of my adult life. So without giving away my age completely, let’s say 15+ years.
What is your favorite thing about living in or near Chicago?
The people! The energy of Chicagoans is unmatched!
What is your favorite Chicago food?
Pequod’s Pizza. The best there is!
If you could meet any famous Chicagoan, dead or alive, who would it be?
I will meet Oprah! I plan on doing some fabulous collaborative projects with her.
Alberto Arias
Occupation
Dance and Fitness Instructor
Neighborhood, Town or Suburb
Streeterville
How long have you lived in Chicago?
57 years
What is your favorite thing about living in or near Chicago?
The lake
What is your favorite Chicago food?
Pizza
If you could meet any famous Chicagoan, dead or alive, who would it be?
Mayor Jane Byrne
Martin Atkins
Occupation
Museum Curator, Educator, Musician, Entrepreneur
Neighborhood, Town or Suburb
Bridgeport
How long have you lived in Chicago?
Since 1989
What is your favorite thing about living in or near Chicago?
The people are amazing!
What is your favorite Chicago food?
Pleasant House Pub anything!
If you could meet any famous Chicagoan, dead or alive, who would it be?
Well, I met Robin Williams briefly but I’d have to say Michelle Obama.
Alex Bean
Occupation
Social Sciences Collegiate Divisional Coordinator
Neighborhood, Town or Suburb
Lincoln Park
How long have you lived in Chicago?
12.5 years
What is your favorite thing about living in or near Chicago?
The world-class architecture and social history
What is your favorite Chicago food?
Tavern-style pizza
If you could meet any famous Chicagoan, dead or alive, who would it be?
Roger Ebert
Elizabeth Blasius
Occupation
Architectural Historian and Writer
Neighborhood, Town or Suburb
Logan Square
How long have you lived in Chicago?
21 years
What is your favorite thing about living in or near Chicago?
From our skyscrapers to the vernacular architecture of our neighborhoods, Chicago’s buildings are the best in the universe.
What is your favorite Chicago food?
An Italian sub from Bari, taken to go and eaten picnic-style on the concrete barrier blocks next to the Metra tracks on Kinzie.
If you could meet any famous Chicagoan, dead or alive, who would it be?
Da Brat or CupcakKe
Maureen M. Boyle
Occupation
Marketing Senior Director, Integrated Marketing and Planning
Neighborhood, Town or Suburb
Bucktown
How long have you lived in Chicago?
20-plus years
What is your favorite thing about living in or near Chicago?
Never-ending things to do and experience – always something new to check out, regardless of season
What is your favorite Chicago food?
Lou Malnati’s pizza
If you could meet any famous Chicagoan, dead or alive, who would it be?
John Hughes
Kathleen Carpenter
Occupation
Docent at the Chicago Architecture Center
Neighborhood, Town or Suburb
Downtown
How long have you lived in Chicago?
All my life except for a brief sojourn to Miami, Florida
What is your favorite thing about living in or near Chicago?
The architecture, the Riverwalk, the lakefront, the water taxi, the bridges, the bridge houses, and Millennium Park concerts.
What is your favorite Chicago food?
The caramel cake at Brown Sugar Bakery. Oh, my.
If you could meet any famous Chicagoan, dead or alive, who would it be?
Fannie Barrier Williams
Rachel Cole
Occupation
Transportation Librarian
Neighborhood, Town or Suburb
Ravenswood Gardens/Lincoln Square
How long have you lived in Chicago?
22 years
What is your favorite thing about living in or near Chicago?
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.
What is your favorite Chicago food?
avern-style pizza. John’s on Western is a favorite.
If you could meet any famous Chicagoan, dead or alive, who would it be?
Either Lucy Parsons or my great-great grandmother.
Tom Dreesen
Occupation
Comedian
Neighborhood, Town or Suburb
I live in Sherman Oaks, CA, but grew up in Harvey.
How long have you lived in Chicago?
I lived there 30 years.
What is your favorite thing about living in or near Chicago?
Cubs, Bears, Blackhawks, Gibsons Steak House, Tavern on Rush, Carmine’s, and the people of Chicago
What is your favorite Chicago food?
Steak at Gibsons
If you could meet any famous Chicagoan, dead or alive, who would it be?
I've met them all.
Dario Durham
Occupation
Content Creator
Neighborhood, Town or Suburb
Lakeview
How long have you lived in Chicago?
I was born here and lived here until I was 15 and just recently moved back 2 years ago.
What is your favorite thing about living in or near Chicago?
The culture. Chicago just has a different vibe you really can’t get anywhere else.
What is your favorite Chicago food?
I love burgers, but the Italian beef combo is top notch!
If you could meet any famous Chicagoan, dead or alive, who would it be?
Barack Obama
Kurt Elling
Occupation
Singer and Musician
Neighborhood, Town or Suburb
I’m with my family in “The Pocket” – a small enclave within Humboldt Park
How long have you lived in Chicago?
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.
What is your favorite thing about living in or near Chicago?
The lake, the architecture, the history, the music.
What is your favorite Chicago food?
Chicago-style polish and regular chips. And a Coke.
If you could meet any famous Chicagoan, dead or alive, who would it be?
Jean Baptiste Point du Sable himself! I’d LOVE to talk about the moment when he said to himself, “Here. This is the place.”
Robbie Ellis
Occupation
Radio Presenter and Producer; Musical Comedian
Neighborhood, Town or Suburb
West Loop
How long have you lived in Chicago?
7 years
What is your favorite thing about living in or near Chicago?
The theatre scene. Always something new to discover.
What is your favorite Chicago food?
Italian beef
If you could meet any famous Chicagoan, dead or alive, who would it be?
Viola Spolin
Monica Eng
Occupation
Journalist
Neighborhood, Town or Suburb
North Side
How long have you lived in Chicago?
52 years
What is your favorite thing about living in or near Chicago?
The lake, food, parks, and people
What is your favorite Chicago food?
Jibarito sandwich
If you could meet any famous Chicagoan, dead or alive, who would it be?
So hard to say. Jane Addams, Ida B. Wells, Ben Hecht, and my great-grandfather Joe Eng.
Jalen Gilbert
Occupation
Actor
Neighborhood, Town or Suburb
Galena
How long have you lived in Chicago?
10 years
What is your favorite thing about living in or near Chicago?
Being in a city with such a rich history and beautiful architecture
What is your favorite Chicago food?
Deep-dish pizza
If you could meet any famous Chicagoan, dead or alive, who would it be?
Bernie Mac. A true legend.
Jamie Nesbitt Golden
Occupation
Journalist
Neighborhood, Town or Suburb
Hyde Park
How long have you lived in Chicago?
Since birth
What is your favorite thing about living in or near Chicago?
#SummertimeChi on the lakefront
What is your favorite Chicago food?
Maxwell Street porkchop sandwich with onions
If you could meet any famous Chicagoan, dead or alive, who would it be?
Mike Royko
Tonika Johnson
Occupation
Social Justice Artist
Neighborhood, Town or Suburb
Englewood
How long have you lived in Chicago?
My entire life
What is your favorite thing about living in or near Chicago?
The Black political and organizing culture
What is your favorite Chicago food?
Too many to name, but I’ll just say, ALL OUR FOOD IS DELICIOUS!
If you could meet any famous Chicagoan, dead or alive, who would it be?
Fred Hampton
Justin Kaufmann
Occupation
Journalist
Neighborhood, Town or Suburb
West Loop
How long have you lived in Chicago?
Since 1994
What is your favorite thing about living in or near Chicago?
It's amazing to live so close to world-class food, architecture, and art.
What is your favorite Chicago food?
Thin-crust pizza from Pizza, Fried Chicken, Ice Cream
If you could meet any famous Chicagoan, dead or alive, who would it be?
Walter Payton
Bill Kurtis
Occupation
TV Journalist and Documentary Producer
Neighborhood, Town or Suburb
Lincoln Park
How long have you lived in Chicago?
More than 50 years
What is your favorite thing about living in or near Chicago?
Its sprawling big-city cultural vitality and sophistication mixed with small-neighborhood openness and diversity.
What is your favorite Chicago food?
Chicago-style hot dog
If you could meet any famous Chicagoan, dead or alive, who would it be?
Carl Sandburg
Terrance Lamonte Jr.
Occupation
Performer and Teaching Artist
Neighborhood, Town or Suburb
The Loop
How long have you lived in Chicago?
Born and raised
What is your favorite thing about living in or near Chicago?
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!
What is your favorite Chicago food?
Anything from Portillo’s
If you could meet any famous Chicagoan, dead or alive, who would it be?
Tomi Adeyemi, author of Children of Blood and Bone
Avery Lee
Occupation
Writer and Performer
Neighborhood, Town or Suburb
I used to live in Lincoln Park before moving to L.A.
How long have you lived in Chicago?
About 15 years
What is your favorite thing about living in or near Chicago?
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
What is your favorite Chicago food?
A Midnight Diner omelette after performing in an underground bar for an audience of one. Well, two, if you count the bartender.
If you could meet any famous Chicagoan, dead or alive, who would it be?
Orson Welles so I can ask him about his classic work: commercials for French champagne and frozen peas. Oh, and also the afterlife.
Dan McDonough
Occupation
Leasing Director
Neighborhood, Town or Suburb
Logan Square
How long have you lived in Chicago?
My entire life.
What is your favorite thing about living in or near Chicago?
Walking the dog (Elvis) along the lakefront!
What is your favorite Chicago food?
Chicago-style hot dog
If you could meet any famous Chicagoan, dead or alive, who would it be?
Harry Caray
Puja Mohindra
Occupation
Actor, Writer, Creator, Producer, Director
Neighborhood, Town or Suburb
Oak Park
How long have you lived in Chicago?
Since 2014
What is your favorite thing about living in or near Chicago?
The authenticity of the people and strong sense of community. I also love Lake Michigan!
What is your favorite Chicago food?
Mexican tortas in Pilsen!
If you could meet any famous Chicagoan, dead or alive, who would it be?
Oprah!
Natalie Moore
Occupation
Reporter
Neighborhood, Town or Suburb
Hyde Park
How long have you lived in Chicago?
I’m a Chicago native.
What is your favorite thing about living in or near Chicago?
The people
What is your favorite Chicago food?
Harold’s Fried Chicken
If you could meet any famous Chicagoan, dead or alive, who would it be?
Gwendolyn Brooks
Mike Oquendo
Occupation
Comedy and Theater Producer
Neighborhood, Town or Suburb
Lakeview/Logan Square
How long have you lived in Chicago?
56 years
What is your favorite thing about living in or near Chicago?
The diversity
What is your favorite Chicago food?
Jimmy’s Polish
If you could meet any famous Chicagoan, dead or alive, who would it be?
Mike Royko
Mia Park
Occupation
Actress, Yoga Teacher, and Special Projects Coordinator
Neighborhood, Town or Suburb
Uptown
How long have you lived in Chicago?
Since 1994
What is your favorite thing about living in or near Chicago?
The vibe, the people who create that vibe, the lake, the parks
What is your favorite Chicago food?
Korean!
If you could meet any famous Chicagoan, dead or alive, who would it be?
Does Abe Lincoln count? The Obamas. Oprah.
Gabe Ramirez
Occupation
Radio and TV Host
Neighborhood, Town or Suburb
I grew up on the North Side and now live in East Garfield Park.
How long have you lived in Chicago?
Luckily, my whole life!
What is your favorite thing about living in or near Chicago?
Being influenced by so many different cultures.
What is your favorite Chicago food?
Jibarito from Papa’s Cache
If you could meet any famous Chicagoan, dead or alive, who would it be?
Mayor Harold Washington
Celena Roldan
Occupation
CEO of the American Red Cross
Neighborhood, Town or Suburb
North Side
How long have you lived in Chicago?
26 years
What is your favorite thing about living in or near Chicago?
Chicago summers, the lakefront, the festivals, and the music
What is your favorite Chicago food?
Pizza – tavern-style or deep-dish
If you could meet any famous Chicagoan, dead or alive, who would it be?
Barack Obama
Kimberley Rudd
Occupation
Public Relations, President of Rudd Resources LLC
Neighborhood, Town or Suburb
South Side
How long have you lived in Chicago?
37 years
What is your favorite thing about living in or near Chicago?
The city’s diversity, vibrancy, and livability
What is your favorite Chicago food?
Pizza
If you could meet any famous Chicagoan, dead or alive, who would it be?
Chaka Kahn or Ida B. Wells-Barnett
Scott Simon
Occupation
Journalist, Broadcaster, Author
Neighborhood, Town or Suburb
Darn, we do not currently live in Chicago.
How long have you lived in Chicago?
The worst thing about currently not living in Chicago is not living in Chicago!
What is your favorite thing about living in or near Chicago?
The worst thing about currently not living in Chicago is not living in Chicago!
What is your favorite Chicago food?
Anything by any member of the Bayless family.
If you could meet any famous Chicagoan, dead or alive, who would it be?
Ida B. Wells
Bryant Smith
Occupation
Art Director and Graphic Designer
Neighborhood, Town or Suburb
Chicago Lawn/Gage Park
How long have you lived in Chicago?
My whole life
What is your favorite thing about living in or near Chicago?
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!
What is your favorite Chicago 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!
If you could meet any famous Chicagoan, dead or alive, who would it be?
Thanks to your show, I already had the privilege of meeting Kurt Elling and Geoffrey Baer. So perhaps Jerry Reinsdorf or Studs Terkel.
Tacarra “Spifster” Sutton
Occupation
Visual Artist
Neighborhood, Town or Suburb
Hyde Park
How long have you lived in Chicago?
My entire life and 33 years in Hyde Park
What is your favorite thing about living in or near Chicago?
We have everything you need here: the best art, best architecture, the realest people, and the best summer experience.
What is your favorite Chicago food?
If we’re talking classic Chicago, I’ll have to give a shoutout to Lawrence Fishery and its fried jumbo shrimp.
If you could meet any famous Chicagoan, dead or alive, who would it be?
Hands down, the late, great Bernie Mac
Ryan P. C. Trimble
Occupation
Entertainment Reporter
Neighborhood, Town or Suburb
Ravenswood
How long have you lived in Chicago?
Since 2016
What is your favorite thing about living in or near Chicago?
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!
What is your favorite Chicago food?
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.
If you could meet any famous Chicagoan, dead or alive, who would it be?
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).
Amanda Vinicky
Occupation
Journalist
Neighborhood, Town or Suburb
Wicker Park
How long have you lived in Chicago?
Five years in Chicago proper, but a lifelong wannabe (suburbanite)
What is your favorite thing about living in or near Chicago?
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!
What is your favorite Chicago food?
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.
If you could meet any famous Chicagoan, dead or alive, who would it be?
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.
Michael Weber
Occupation
Executive Producer
Neighborhood, Town or Suburb
River Forest
How long have you lived in Chicago?
My whole life
What is your favorite thing about living in or near Chicago?
Lake Michigan
What is your favorite Chicago food?
Anything Italian
If you could meet any famous Chicagoan, dead or alive, who would it be?
Harrison Ford would be cool.
Patty Wetli
Occupation
Digital Reporter with WTTW News, on the nature and environment beat
Neighborhood, Town or Suburb
Lincoln Square
How long have you lived in Chicago?
Closing in on 30 years
What is your favorite thing about living in or near Chicago?
I love being able to walk everywhere, whether it’s to Walgreens or the grocery store or a movie theater or a park.
What is your favorite Chicago food?
Scooter’s Frozen Custard. Their whiskey caramel flavor is... chef’s kiss.
If you could meet any famous Chicagoan, dead or alive, who would it be?
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.
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