Oprah Winfrey as a Tour Guide with Chicago Detours

It was a surprise for both Oprah Winfrey and me. I had been looking to bring on one more guide to fill in our busy schedule of walking tours, and the new “Our Chicago Sound: Jazz Blues and Beyond” music history tour by bus. Yesterday, after a usual 12-hour work day – standard for a new business owner – I decided to grab a coffee and study up with a book called, Story Jazz: A History of Chicago Jazz Styles.

I was a little annoyed when I heard a voice say, ‘Oh, that looks like a good book.’ I mean, when you’re reading you usually don’t feel like talking. That’s why you’re reading, right?

Well, it ends up that it’s Oprah sitting next to me at the Starbucks on Madison and Racine. We started chatting about Chicago history, music, jazz and blues, and the educational nature of Chicago Detours tour company, and then Oprah stated, “I feel that luck is preparation meeting opportunity.”

I really had no idea what she was talking about at first, so I just stared at her looking a little confused. And then Oprah said, “I still have my feet on the ground, I just wear better shoes.”

Ah-hah. She wants to lead walking tours. She was dropping hints. s-OPRAH-large

So I guess if Oprah wants a job at your company, what can you say? Apparently with the “Farewell Season” she’s been wondering about her next step. I had her send in her resume and go through an interview, and when I offered her the job I had my camera ready (see the pic). She’ll go through 8 weeks of training just like the rest of our tour guides. I’m just wondering though about a Chicago Detours 1-year anniversary party – maybe she could take all of us on a cruise?

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Ellen

Private Tour Coordinator and Tour Guide

There is no shortage of things to discover in Chicago—I love being an urban explorer and uncovering its hidden places. I have an MA in Public History from Loyola University Chicago, and I have worked as a museum educator and kindergarten teacher. My desire to learn new things fuels my passion for educating others, which I get to experience every day as a Chicago tour guide. I live in the northern neighborhood of Rogers Park.

“Our guide Ellen was exceptional and gifted with a great personal touch.”
Robert
GetYourGuide

Jen

Tour Guide

Whether you are a first-time visitor or a lifelong resident, the vibrant history and modern majesty of Chicago never ceases to amaze. I’m a graduate of Columbia College with an M.A. in Interdisciplinary Art. I’ve worked for many years as an educator at City Colleges of Chicago. As tour guide at Chicago Detours, I integrate my enthusiasm for culture and architecture with my passion as an educator. West Town/Noble Square area is home for me.

“Jen was a perfect storyteller and kept us spellbound for hours.”
Heather
TripAdvisor

Elyse

Tour Guide

With our Chicago neighborhoods, vibrant cultural institutions and nearly two centuries of larger-than-life stories, there’s never a dull moment here! I’m a fifth generation Chicagoan and a graduate of Washington University in St. Louis. In addition to guiding tours, I’m a creative writer and amateur genealogist. I also enjoy the city’s dynamic theater scene. You can also read overlooked stories from 19th-century newspapers on my “Second Glance History” blog. I live in River North.

Anthony

Tour Guide

Chicago is unique as it always evolves into the future while holding on to the past. I’m fascinated by how people latch on to old architecture but happily pave over others. My background is in theater and performance and I’ve been a tour guide here for more than 10 years. Currently I’m finishing my Master’s in Public History at Loyola University because I love to teach the history of this scrappy city. I’m in the Edgewater neighborhood.

Marie

Operations Coordinator and Tour Guide

Chicago’s history is so fascinating, you could spend a lifetime uncovering its secrets…I’m willing to give it a try! I have an M.A. in US History from the University of Nevada-Las Vegas and then pursued doctoral studies in Urban History at the University of Illinois at Chicago. I love to learn new aspects of Chicago’s rich history and then share my knowledge as a tour guide with Chicago Detours. I live in Ravenswood.

“Marie was a bubbling fountain of information and contagious enthusiasm.”
Lorit
TripAdvisor

Sonny

Operations Coordinator and Tour Guide

As a fourth generation Chicagoan, I have been living and loving Chicago by bike, on foot, public transit or automobile. I am a graduate of UIC where through the College of Urban Planning and Public Affairs, began my eagerness to understand the nature, history and impacts of urban planning and development. It is incredibly rewarding to give back to this wonderful city by helping out in the office of Chicago Detours. I live in the incredibly diverse neighborhood of Albany Park.
“Sonny was extremely knowledgeable about all things Chi-town.”
Wade K
TripAdvisor

Alex

Content Manager and Tour Guide

Chicago has so many neighborhoods, buildings, and by-ways that it’s hard to go long without seeing something new, or something familiar from a new angle. I studied Cinema History for my M.A. from the University of Chicago. I’ve worked as a culture writer for various publications and as an educator of the humanities at the City Colleges of Chicago. I’m thrilled to share my love of this city’s busy past and unique architectural spaces with Chicago Detours. I live in the Chicago neighborhood of Lincoln Park.

“Alex was fascinating to listen to. He clearly knows his history and it shows.”
Katie K
Yelp

Amanda Scotese

Executive Director and Tour Guide

I’m an interpreter of personal stories from the past and the city’s landscape. I love to imagine what originally happened inside old unmarked buildings, and what forces have shaped their design. I studied Chicago history, architectural history, and anything Chicago-related through my M.A. in the Humanities at the University of Chicago. My love for stories was enriched by my B.A. in Literature from the University of Michigan. I’ve written travel articles for publications like Rick Steves’ Italy best-selling travel guides, the San Francisco Bay Guardian, and The Chicago Food Encyclopedia. I live in the Chicago neighborhood of West Avondale.
“You can TELL Amanda is hyper-passionate about doing the research and getting the story that nobody’s heard before.”
Shelby F
Yelp

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