What Goes Into Starting a Tour Company?

Starting a tour company is a daunting challenge! Here Amanda, our Executive Director, shares her experience as an entrepreneur with her tour company in Chicago, which was founded in 2018. In 2020, the tour company became a virtual events company. Here are her thoughts on going into small business in the travel and events industry.

amanda chicago tour guide

How do you start a tour company? 

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 interests come together into a career. During my first year of college, I was awarded a summer scholarship to travel to Italy for language study. That trip solidified my love of learning languages and exploring the world.

Since I wanted to return to Italy, I thought I could try getting a job in tourism there! Rick Steves’ Europe hired me on as a Tour Guide and Guidebook Researcher. My specialty was Southern Italy. For a decade, I worked as a tour guide and traveled back and forth between Italy and the States. I took Americans around the country on guided multi-day tours. I learned a lot about being an educator and trip organizer from my tour guide work with Rick Steves.

Living between two countries over the years was a bit disorienting. I decided to bring my travel expertise back home, with the goal of starting a tour company. Before launching Chicago Detours, I wanted to really know Chicago history and architecture inside and out. I pursued an advanced degree and got accepted to the University of Chicago. My interdisciplinary degree, an M.A. in the Humanities, allowed me to study anything from Black Chicago History to the history of skyscrapers. So that, in short, is how I came to make Chicago Detours happen!

Starting a tour company
Amanda Scotese, Tour Guide and Executive Director, in action. Photo by Marie Rowley.

Getting a tour company off the ground

Being a new small 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 travel 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.

The learning curve for starting a small business

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 which he assigned to 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?

Amanda Scotese starting a tour company
Starting a tour company is a lot of work, but it’s well worth it in the end. Photo by Pawel Scrabacz

What are you most proud of as a tour company owner?

When starting a tour company I knew it’d have to be unique. 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 professional Chicago 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.

Our tours 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.

Book Senior Group Tours of Chicago Neighborhoods
Photo by Alex Bean.

Where do you see the tourism industry going?

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 walking a route outlined in a guidebook. Now you just go anywhere and make your decision as to when and what kind of information you want to access.

Recently, people want to find what makes a place unique. Gone are the days of being on a trip and shopping at chain stores. People want experiences, and when they travel they want experiences that they cannot get elsewhere.

Making Chicago tourism a unique experience

That being said, a person cannot necessarily curate a special experience on their own. 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 both 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. There’s even a place where you can throw axes for fun. 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. It’s about learning, entertainment, and enjoyment that phones cannot replicate. And this is indeed what Chicago Detours does with our tours of interior architecture, historic bars, jazz and blues, culinary history and Chicago neighborhoods. I could not have guessed all this when the idea to start a tour company first occurred to me.

This post has been adapted from an interview which originally appeared in Voyage Chicago.


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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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