An Inside Look at a Tour Company and Guided Tours

A journalist interviewed me some time ago, and while not all the questions were featured in the article about guided tours, I thought it might give some good background on Chicago Detours and how our tour company came to be.

What kind of services does Chicago Detours offer?

Chicago Detours offers guided walking and bus tours of architecture, history and culture to public and private groups. Guided tours include interior architecture, historic bars, and jazz and blues history of Chicago. We blog about overlooked or forgotten stories of Chicago architecture and history, too.

chicago detours guided tours amanda scotese
This is me! Taken before doing a presentation on Chicago architecture at the Union League Club.

Can you tell us about your educational and professional background?

I focused on studying Chicago’s history, sociology, and architectural history through the Masters of Arts Program 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, where I also extensively followed my passion for art history.

What was your post-school, professional training like?

With Rick Steves group tours around Europe, which I led as a tour guide for a decade, we had several weeks of training via shadowing other guides and then also doing our own talks to the group, either on the bus or on walking tours around Italian cities and town. Really the only way to be a tour guide is to do it because good tour guides make it look so easy, but then when you actually go to talk you realize that being eloquent with your words and clear with your ideas is a lot more challenging than it seems.

Did you initially find it easy or difficult to find a job in the field?

I got lucky and applied at the right place and the right time. It wasn’t difficult at all.

How did you come to be a tour guide?

I had traveled a lot in Italy and randomly heard from a friend about the possibility of a job as a tour guide there for multi-day group tours. I had never even thought of it as an actual profession. I got hired while still in college to be an assistant guide for tours with a company I will leave unnamed. They were programs in Southern Italy, and I had spent a couple summers in Italy. I did it for a summer, and the company was really disorganized, the clientele were high-maintenance, and the pay horrible. It just didn’t seem like a viable career so I pursued working as a freelance journalist.

Five years later, I horribly missed Italy, and thought that the whole tour guiding thing was pretty cool, so why not try with another company? I got hired with Rick Steves, and I’ve learned so much from my colleagues, and from doing the guidebook updates with Rick. They have been an awesome company to work for.

What is your definition of a tour guide?

A tour guide is a teacher who presents cultural insights into art, architecture, and the cityscape.

What is your day-to-day routine like?

I am a small-business owner with a full-time employee and a team of five tour guides, so my day-to-day involves lots of email communication with private tour clients, my team, our webmaster, legal team, accountant, and graphic designer. Beyond managing the business, everything for the most part revolves around the giant task of marketing.

Can you tell us about the places/types of jobs you’ve worked in, how they were different from each other and how they have given you valuable experience?

Having guided around Italy and in Chicago, I have taken people on tours through the tiny streets of Venice, up the slopes of volcanoes, and into magnificent lobbies of 1920s skyscrapers. The actual job as tour guide is not much different. The main difference in navigating groups through cities is that we have a lot more space in Chicago and everything is bigger!

amanda picasso tour guide chicagoHow would you describe the rigors of your profession? 

Challenges can be when high maintenance people interrupt presentation or “know it alls,” but honestly these rarely happen.

How would you describe the rewards of your profession? 

How do I list all the rewards of being a tour guide? There are so many. Rewards come from getting people excited about history, architecture and the world around them. The amazing people you meet and the comments they share. Creating a memorable experience for people is very satisfying. Being able to work actively and not in front of a computer. Constantly learning.

How has technology affected your day to day, if at all, in recent months/years?

It’s always changing and somehow making communications more efficient and more complicated at the same time!

I’ve noticed from traveling abroad that there are many “free tour” companies that only ask for tips at the ends of their tours… has this caught on in America? If it does, how will this affect your industry?

They are trying to get it to catch on, but I think most potential tour guests know that you get what you pay for. There’s a value in paying for a tour with a professional guide.

What is the biggest misconception (if any) about being a tour guide?

That it is a hobby. This is my profession – it takes years to be able to understand what ideas grab people, how to tell a good story, how to choose your words in a poetic way, and how to design and pace an interesting tour. Yes, I have made my passion into a job, but it is definitely much more than a hobby.

Is there a particular moment in your job history that you wish you could relive?

While I’ve had many special moments, I wouldn’t want to relive any. I’m more excited about the future.

Where do you see Chicago Detours going in the future? 

I’m really excited about adding another full-time employee to our team so that we now have 3 full-time employees and two part-time tour guides.

Do you have a favorite tour joke you can share with us?

Jokes just don’t work well written down – you have to tell them!

What is the key to giving a good tour?

Enthusiasm, clarity, and being concise.

— Amanda Scotese, Executive Director


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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.”


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.”


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.


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.


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.”


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


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

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

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