Chicago Detours 2021 Year in Review

It’s all been a blur but an exciting 11th year in business! Change is certainly the theme for all our lives, and especially for businesses.


In winter of 2021 we blazed forward with the design of new virtual tours. Over the years, Marketing Manager Marie had compiled an incredible list of Chicago women that the team had researched for in-person tours, virtual tours, and our hundreds of blog posts. With a list of close to 100 women, we then selected eight women who worked in a range of industries or subjects, came from various eras of history and diverse backgrounds.

Because we chose lesser-known figures of history, our research involved a lot of sleuthing! We then crafted their stories, found and licensed images, and tested interactive elements. We flew by the seat of our pants to bring “Badass Women of History Virtual Event” to life in March, which is of course Women’s History Month.

badass women virtual event zoom

Guests described the experience as “fun, engaging, informative and inspiring.” The word “inspiring” came up as the biggest theme. It was featured on NBC Chicago, WBEZWGN Radio and more. 

Then it was a struggle to come up with the angle for our “Breaking Down Chicago Neighborhoods” virtual tour. How can one fit that into one hour? How do you choose which neighborhoods are covered and which are not? Do you prioritize the history, the people, or the architecture? It was a huge challenge. Ultimately after plenty of dead ends, we decided that the underlying concept is how similar the different areas of the city can be, rather than focus on what makes them all different. We love what we came up with, and local corporate teams that we regularly work with particularly enjoyed it. We booked a ton of both of these virtual events for corporate entities, universities, and non-profits.


Let’s remember that late winter of 2021 was when the COVID vaccine had begun to arrive for many of us. We were all feeling hopeful! While many tour and event companies and cultural organizations were getting ready to reinstate in-person events, we made the decision to only open for private groups. Here’s a picture of the first bus tour we had done in a year and a half! Alex and Amanda were each in a bus, touring Chicago neighborhoods with almost 100 future priests from Loyola University. Everyone was vaccinated. The energy and enthusiasm was indelible. Many hoots and hollers were had as you can see in this picture!

We reopened for in-person public tours in December with a newly redesigned “Downtown Holiday Walking Tour.” It was incredible to experience downtown abuzz again! People bustled about on the sidewalks, a DJ partied inside Macy’s, and we sipped on hot Tom & Jerry holiday cocktails at Millers Pub. It was quite magical to bring perfect strangers together on a public tour again, but alas the Omicron variant arrived…


In 2021, we produced more media that explores Chicago neighborhoods and downtown, from its history to food and design. Here are just a few highlights of our custom projects of 2021:

  • The Chicago Detours team custom built “Diverse Cultures of Evanston Virtual Tour” completely from the ground up as a fundraising event for a private client. We researched digital archives, compiled images, and sifted through 360-degree Google Street View images to tell this story.
  • We wielded our research in the latest trends in community-based tourism practices to design neighborhood tours for a corporate client. It was a 600-person diversity and inclusion event.
  • We hired a video production crew to produce an on-the-streets walking tour of Chicago for a virtual conference.
video link to on the street downtown walking tour


More awesome things happened to Chicago Detours in 2021:

  • For the second year in a row, Chicagoans voted us as “Best Tour of Chicago” runner-up, second only to the largest tour company in the city.
  • Inc Magazine included us in “How 5 Small Businesses Reinvented Themselves During Covid.”
  • Amanda’s was invited to present on panels for Choose Chicago, the Chicago Tourism Professionals Association, and VRARChicago with her expertise in the tourism industry.
  • Chicago Detours was nominated for the 2021 Chicago Innovation Awards for our innovative response to the industry shutdown during the pandemic.

Happy New Year to all. Here’s to 2022! Thank you for keeping up with what we do. More good things to come!

The Chicago Detours Team


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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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