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Meet Amanda Scotese of Chicago Detours

Today we’d like to introduce you to Amanda Scotese.

Amanda, let’s start with your story. We’d love to hear how you got started and how the journey has been so far.
I launched Chicago Detours in July 2010 in order to share the architecture, history, and culture of Chicago through guided tours. I’d always loved storytelling, art, architecture, and travel and had never imagined that I would be able to make these interest congeal into a career. My first summer of college, I was fortunate enough to be awarded a scholarship to travel to Italy for language study. That trip began my love of learning the language and exploring the world.

I got my B.A. in Literature from the University of Michigan. I chose to major in literature because I had always had a love for stories, and had thought I might be a writer someday. After undergrad, I took a somewhat successful stab at being a journalist and found that it just wasn’t social enough for me.

At that point in my life, I wanted a way to return to Italy. Rick Steves’ Europe hired me on as a Tour Guide and Guidebook Researcher. Southern Italy was my specialty. For ten years, I lived my life going back and forth between Italy and the States. I took Americans around the country on guided multi-day tours. I learned so much about being a good educator and trip organizer from my work with Rick Steves.

Alas, living between two countries was disorienting, so I decided to bring my travel expertise back home. Before launching Chicago Detours, I wanted to really know that I was indeed an expert on Chicago so I pursued an advanced degree. I studied Chicago history, architectural history, and anything Chicago through my M.A. in the Humanities at the University of Chicago. So that, in short, is how I came to make Chicago Detours happen!

We’re always bombarded by how great it is to pursue your passion, etc – but we’ve spoken with enough people to know that it’s not always easy. Overall, would you say things have been easy for you?
Being a new business owner is never a smooth road! In the beginning, I arrogantly thought that I’d be different. I was very quickly proven wrong. It was really hard those first couple years!

My fantasies of being a business owner were, indeed, complete fantasies. I thought I might do a tour or two a day, pop into the office for an hour, and then go hang out on the beach. I quickly found out that marketing was a much larger task than I’d imagined. The difficulty of even getting people to notice you meant that I often rejoiced at getting two people to come on a tour! I also realized that I would not be able to make Chicago Detours happen as a one-person venture.

One of the big issues in the early days was that I didn’t know I was offering something unique. I wanted to bring people to explore stories and places locals don’t even know (which is our tagline today). This philosophy meant I would, for example, take them into buildings, instead of just talking about architecture from the sidewalk.

In those buildings, I’d share concepts, ones I’d pared down from scholarly research, and told forgotten stories that I’d culled from archives like personal diaries or vintage travel guidebooks. I wanted to make a fun and educational experience. Something more than a guide who lists dates and names and tosses out rehearsed corny jokes.

But I didn’t realize that the tours I was creating were much different than traditional expectations. I often got frustrated when people like hotel concierges didn’t understand what I was trying to do. I forgot what we all learned in business class – for new products, there’s a bell curve. You’ll get early adopters and then only later do you get the masses that follow.

That’s exactly what happened with Chicago Detours.

Part of growing as a company is making mistakes, too. You have to make mistakes to learn. For example, I lost thousands of dollars because I trusted a recommendation instead of digging in myself.

A friend connected me with an agency for a marketing project. This guy’s company and its services were not honest. I got charged $100 an hour for a PR project to which he assigned a woman whose job was actually to order cafe equipment for him. I got scammed out of thousands of dollars, which was a ton of money for a new business owner. I learned to always shop around, even when I’m urgently trying to get something accomplished.

More recently, it’s a struggle to stand out because a number of tour companies have opened up with similar concepts, tour routes, branding, and even language straight from our website. Imitation is the best form of flattery, right?

So, as you know, we’re impressed with Chicago Detours – tell our readers more, for example what you’re most proud of as a company and what sets you apart from others.
Chicago Detours offers guided walking and bus tours of architecture, history, and culture to public and private groups. We do fun stuff, like jazz and blues, Chicago neighborhoods, interior architecture downtown, and historic bars.

We also blog about overlooked or forgotten stories of Chicago architecture and history.

I’m proud of how awesome our tour guides are. I hire smart, fun and passionate people who are good educators. They have a lot to do with how we are one of very few Chicago tour companies with five solid stars on both Yelp and TripAdvisor.

What sets us apart from other tour companies is many. One is that we curate experiences versus having a person just recite a bunch of dates and names. To further explain, we may integrate food, drink, and games in between commentary and walking into unique architectural spaces. The tour guides foster a more interactive dynamic, such as by asking guests questions to get them actively thinking about new ideas in architecture and history.

Our tours are also employ the presentation of media, like historic photos and film clips, through the use of either shared iPads or video screens on a bus. And then our ethos! We like to say that we bring people to explore stories and places locals don’t even know. The content of our tours comes from digging through old books, newspapers, magazines, and various archives as well as scholarly articles to share stories and ideas that don’t exist elsewhere.

Where do you see your industry going over the next 5-10 years? Any big shifts, changes, trends, etc?
Travel is changing so rapidly because of the access to information that people now have at their fingertips, and as a result, people are making plans last-minute, from booking their trip to finding a restaurant to eat at.

This is a huge trend. Even just being able to look at a building and google the history of it means that anyone – whether on a trip or a resident walking down a city street – can decide in the very moment as to what kind of information they want when they want. It’s very different than the old-school way of walking a route that is outlined from a guidebook. Now you just go anywhere and make your decision as to when and what kind of information you want to access.

The biggest trend I’ve seen growing recently is the desire to connect with the unique qualities of a place. Gone are the days of being on a trip and shopping at chain stores that you can get back home. People want experiences, and when they travel they want experiences that they cannot get in other cities or when they are back home.

While spontaneity is at their fingertips, on the other hand, a person cannot necessarily do independently is curate a special experience. Airbnb Experiences, for example, is trying to connect people with opportunities that they could not create on their own (yet are still available to book through their smartphones of course).

Airbnb Experiences are crafted not just around an activity as well as the unique character of the host themselves. We see experiences becoming more developed in the ever-competing market of bars, for example. Barcades” are popping up all over, as well as escape rooms with bars, and even a place where you can throw axes for fun.

And as a side note, and speaking of bars, we will continue to see a rise in interest in food and drink!

I believe the future of travel is in curated travel experiences that give people the personal connections, learning, entertainment, and enjoyment that their phones cannot. And this is indeed what Chicago Detours does with our tours of interior architecture, historic bars, jazz and blues, culinary history and Chicago neighborhoods.


  • Public walking tours start at $22 per person.
  • Private walking tours start at $250 flat rate per group.
  • Private bus tours start at $600 flat rate per group.

Contact Info:

Image Credits:

Kate Joyce, Pawel Skrabacz

Getting in touch: VoyageChicago is built on recommendations from the community; it’s how we uncover hidden gems, so if you know someone who deserves recognition please let us know here.

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