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Oprah Winfrey as a Tour Guide with Chicago Detours

By Amanda on April 1, 2011


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?


Chicago Detours offers guided walking and bus tours of architecture, history and culture to public and private groups. We are a passionate team of educators, historians, artists and storytellers, and are proud to be one of very few tour companies in Chicago that is rated five stars on both Google and TripAdvisor.


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