A Transparent Review of Our 2020

We here at Chicago Detours annually take a look back on the journey our small business has taken over the year. The  reflection for 2020 is a unique one, and one that I’d like to share with a great deal of transparency. 

For us and for all of you, 2020 has felt like a decade. At the beginning of the pandemic, we faced the fallout of tourism while sending off thousands of dollars in returned tour payments to anyone from individuals to big companies. Instead of celebrating our 10-year anniversary, I ended up pretty much leading a start-up. We went through the crazy process of transforming our business to be a virtual events company. 

We had stressful moments, and some funny ones, too. Here is our story of 2020. 

chicago detours nightlife history zoom virtual
A virtual event guest sent us this hilarious and accidental overlay of my face on images from Chicago nightlife history.


The onslaught of the Covid-19 pandemic in March spelled the abrupt end of our winter walking tours and bus tours. We had to figure out how to adapt in a real hurry. First, we wanted to contribute to the conversation by writing a blog post, “How Has Chicago Responded to Historic Epidemics?” 

We had been ready for a busy 2020 with two new tour guides who were just completing the first phase of their training. Sadly, they were supposed to do their first tours exactly the week that we had to shut down. As a business owner, I had to make quick decisions to ensure the survival of my business. There was no way that new guides could have work. How was I as business owner going to figure this out?

For the first time in ten years of business, I had to lay off an employee. One of the least appealing aspects of being anyone’s boss for me had been the pressure of being responsible for anyone’s livelihood. Laying someone off was never something I wanted to do. And on top of this all, it was a time in which anxiety was high from pandemic fears. 

virtual tours collage
Each image in this collage designed in March corresponds to the various virtual tour topics.

How to design virtual tours?

Zooming out (no pun intended) from the immediate pressures, I was facing the harsh possibility that the business that I worked so hard over the past decade to build might have to shrink to just me.  

Like any small business owner, I am not one to give up easily. We got online. As far as we know, we were actually one of the very first Chicago companies to offer live, virtual events in 2020. Being small meant that we could pivot quickly, without being bogged down by bureaucracy. Additionally it was a huge advantage for us that our tour guides are super passionate and knowledgeable, versus the more mass tourism where guides are either actors or volunteer docents. We easily had a ton of stories about Chicago history and architecture to share! We studied what other tour companies were doing. Then we pulled together ideas from our 10 years as a tour company. Thus began our Zoom-based virtual tours and presentations.

We experimented with different formats for sharing our stories live via Zoom meetings. The term “virtual tour” was popping up everywhere, with a lot of confusion as to what that actually means. This YouTube video of “Chicago Building Types in Four Neighborhoods” shows one early experiment where four of us tour guides collectively toured our own neighborhoods. That was a ton of work to orchestrate! We had to figure out another way. 

plowing forward in a pandemic

We had a glimmer of hope from the incredible support we received from past tour guests, associations, family and friends. The praise, encouragement, and donations we received for these free virtual tours made us feel valued. Hundreds of people registered for them every day. We got a ton of press recommending us for ways to combat lockdown-induced cabin fever.

The free, virtual tours would not, however, be a sustainable way to support our small business. We had to cover payroll, rent, and all the other expenses of a small business. It became very clear that the pandemic would be longterm. We were further venturing into unknown territory.  

We began to refine our events. Our Chicago Detours team decided that “virtual tour” meant for us that we would feel like we were moving through space by partially using 360-degree images from Google Street view. We also had more photo-based virtual events that had more of a lecture format. See here for more about the early evolution of our virtual events. 

Every day I didn’t know how the business could continue to employ the team. But then we received a PPP loan, and frantically we had to continue to plow forward. Those two months in which we had this small business loan – which may or may not get forgiven – were overwhelming. Our workload swung all over the place, from designing the virtual events to marketing them. 



I have not publicly shared what I really went through. The terms of the PPP loan were that I had eight weeks to spend it. They changed those terms at about week six, and it was too late for me to change anything. We were out of the loan money by week eight. Plus my energy was drained. And my confidence in my abilities to be a business owner was waning. 

At about that time, lockdown was easing up. I had told employees that it was their choice if they wanted to do tours. In an incredible display of teamwork and devotion to the business for them to have chosen to do them. We tried offering a few walking tours. But it just wasn’t worth making people take public transit downtown, and barely anyone was signing up. We shut the tours back down. 

So in early July, I was faced with a big decision. We had no reliable means of generating revenue. And of course, a business without revenue will go bankrupt. I had to come up with a plan. 

To give you some background, my current employees have been with Chicago Detours for anywhere from two to six years. I feel an incredible about of gratitude for their efforts, and for their faith in me as a leader. I could not see giving up on them as an option. If I had focused on fear, I would have taken away everyone’s job and we would have broken up as a team. The potential pain of that route was just not feasible for me.

I had to pull it together. Without any solid idea of how we would make money, I chose to keep everyone’s hours at 100% and move forward. And at that point, attendance for our virtual tours had very much dwindled with the easing of lockdown and the coming of summer. 

I worked 12 hours days for about two weeks straight after the loan money had ran out. I’d given myself a deadline to come up with a plan. Mind you, this is after already been overworking for months. To feel like I was making an informed choice, I dug into market research. I started reading The Lean Start-up by Eric Ries. It really boosted my business-owner confidence because I was already essentially following its principles from my gut. 

I also had tons of conversations with mentors and esteemed friends. With minimal idea of how to turn this new format into a sustainable and profitable business model, I searched for a target to shoot for. It was a huge gamble, but I trusted that our awesome team would rise to the challenge of getting us through 2020 together.

After those two weeks were up, we had a sweltering social-distanced strategic planning meeting. I ultimately proposed we focus on remote team building events. And then, without having prepared any marketing, the requests for virtual events for groups started coming in. These requests came mostly from past private tour clients, word of mouth, and people who had experienced our free virtual tours.

Getting our graphic design on!


We held weekly Strategic Planning Meetings over the summer. Pivoting would be a constant process. We hashed out what was working and what wasn’t in our virtual events during weekly virtual meetings. A good friend of mine who used to manage out-of-the-box style strategic planning meetings offered to help. We had a sweltering meeting in my front yard to brainstorm possibilities.

We also had a socially-distanced picnic. In all our virtual and in-person sessions, we brainstormed new interactive elements, like games and creative challenges, and tried to map a vision for how to reach paying audiences for our corporate team-building events.

We spared down our product offerings and focused on perfecting four strongest and most popular events. Product development took months, with lots of surveys for feedback from past clients. We conducted focus groups and did additional product testing. We received great press from the Chicago TribuneBlock ClubThrillist, and NBC. That said, we’re thoroughly enjoying this new line of work and hosted some really exciting virtual events. 

Planning for the Present and the Future

2020 has been such a whirlwind. Don’t you wish we could stop the world economy for a month so everyone could take a month-long vacation? Not a good idea in execution, but definitely in theory!

Most recently, our “Virtual Holiday Stories Happy Hour” ended up being an awesome team-building event, and we offered it to the public for families and friends to connect from afar. We got press for it; you can find some here, here and here. We also set up our Chicago Detours Store for gifts for curious people who love architecture and history. 

 After having poured thousands of hours into creating our virtual events, we have hosted more than 27,000 guests. It’s been a richly rewarding experience for us. And you can get a glimpse of our 2020 achievements on our YouTube page for some earlier virtual events and our more recent livestreamed neighborhood walks on Facebook. We also have a 12-part Chicago Architecture Crash Course that we created. It’s  available for a three-month-long rental.

Chicago Detours guides boat tours Chicago fire boat
Team photo from 2019, when none of us had any clue what 2020 had in store.

the pivot is not done yet!

We have more fun planned in early 2021. This January, we’re hosting virtual events for the public about Innovations at the 1893 World’s Fair and Chicago’s Food History. We’re also focusing on our Badass Women of Chicago History virtual event for conferences and corporate groups. It includes some pretty awesome swag – our Badass Women Journal gift that we created. 

People keep talking about how much 2020 sucked. But, let’s be grateful that we are having conversations about race that we need to have. Let’s celebrate that we have gotten a chance to reassess what we really value and care about. If 2020 has taught us anything, it’s that we shouldn’t take anything for granted. We’ll keep you informed about what the future holds as soon as we know it. The pivot is not done yet!

We have a lot of people to thank for joining us. We’re looking ahead to our next phase as a company. And no matter what, we will share stories of people, places and buildings across history.

– Amanda, Founder and Creative 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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