Uncovering the Secrets of the City with Chicago Detours

On a recent trip to Chicago, my first visit to the city, I took an architectural history tour with Chicago Detours, and was so glad that I did. I love architecture anyway, and the tour took me through underground passage ways and through back doors into places I would never have found on my own. The tour was interesting, and way better than any other walking tour I’d ever been on, partially because it embraced technology and used iPads to share old videos and images to create context as we explored the city, but also because Amanda Scotese, owner of Chicago Detours, who was leading us, was so fun and knowledgeable.

After, I cornered Amanda to ask more about what she was doing, and she further shared her enthusiasm for her beloved Chicago. Here’s how our conversation went…

So Amanda, what was your motivation for starting Chicago Detours? 

I’ve always loved exploring and looking at architecture, and I just love sharing that with people. Tourism is a big deal here in Chicago, and I looked into what tour options there were in the city then thought, “Well, what about the tours for people that are more like me? A little younger, a little more adventurous, a little more well traveled – the people who don’t want to do just a standard bus tour?” Our three year anniversary is coming up this June, and we are now running the tours six days a week, so thankfully there are lots of people that are looking for this kind of experience.

What are the other tours that you offer?

We also offer a historic bar tour, and that one is still very much integrated with architecture. We’re looking at buildings from the outside and inside, and the features of the architecture to get a sense of the history and an insight into the past. Everything that we are looking at on that tour is to do with entertainment history, so we go into an old speakeasy, an early jazz club, we talk about vices and nightlife in the 1950s. We look at the city as a playground, and how people have had fun in Chicago over the course of its history. That tour is a lot of fun, and often exceeds the expectations of the people who go on it, as they tend to expect a pub tour with a couple of stories thrown in. This covers the kind of history that no-one writes about and offers some really different angles. I had to do some creative digging to find these stories. 

The digging that you do is obviously part of what makes your tours so interesting. You clearly do your research. 

I do say at the beginning of our tours that what differentiates us is that first, we have a more interested dynamic, and that second, the content of the tours is really unique, as well as how we deliver that content with the iPads. We also blog about the city, and are looking at developing a mobile app too. With all the info we have, we could take this in a million different directions and share all this in so many different ways.

Was your background in history?

In high school I always hated history, and it wasn’t until I studied art history in college that I started getting really excited about learning about the past. Then I had some really good professors that taught me about how stories from the past matter, and that meshed with my interest in literature, which I majored in. In a month, I will have officially completed my Masters of Arts in the Humanities from the University of Chicago. I did the program with the understanding that I’d start this company, and because I wanted to really know what I was talking about. Studying for that degree has been an invaluable experience, as I took classes in all kinds of different areas of Chicago’s history and architecture, and got to explore the city from a lot of interdisciplinary perspectives.

Are there certain people that seem to take your tours?

We get a lot of hipper travelers, such as younger couples in their 20s and 30s, but then we also get a lot of older suburbanites who have lived in Chicago forever, feel like they’ve done everything and want to try something different. One of the really cool things about our tours is that they really do attract people of all ages, and it is really more about having a passion for the city. We get a lot of people doing the tours as a good date night thing to do. We love getting informed and engaged travelers who really get the most out of our tours.