We Want to Curate the Best Virtual Experiences about Chicago

When I wrote for the Chicago Detours blog last spring, it was about our “temporary transition” to offering virtual experiences. Months later, virtual experiences are both our present and future. We’d like to share here how we have successfully transformed a walking tour company into a virtual events company. We put our creative minds together along with our decade of doing tours for conferences, corporate groups and universities in order to tackle these new challenges with some awesome results.

We hope you can join is in the next few weeks for our Virtual Holiday Stories Happy Hour. We spent hundreds of hours researching and refining this fun, interactive virtual experience that celebrates Chicago’s many holiday season traditions. And our knockout event for 2010 is Badass Women of History. We will offer it to the public a few times during March, which is Women’s History Month. And it is always bookable for a private team-building activity that explores diversity and inclusion.

virtual tours Chicago Detours

Creating Content

We spent April working out our approach to storytelling and presentations and then our team of five put the pedal to the metal. We had figured out what platform we wanted to offer these events, and we went with the new industry standard (Zoom).

We quickly found that the live format (versus a recording) made it exciting. People could comment in real-time, making the presentation a two-way street. It brought people together in a shared experience, and therefore combated quarantine loneliness. Our virtual events were enormously more popular than we’d imagined, and we were getting 200-300 guests with minimal marketing. People were showing up to every one, and inviting friends to join.

Nearly every day of the week had a virtual tour or “Historic Happy Hour,” all of which were original creations. We relied on the deep well of information and stories that we had developed over 10 years as a tour company, but it was still a ton of work.

Creating dozens and dozens of unique virtual tours meant hours of research, editing, presentation refinement, fact-checking, and editing. Not to mention the time spent in front of the camera! We realized by the end of May that we needed to devise more structure. As “pivot” came to be the buzz word du jour, we were basically eating it for lunch every day. With no one understanding yet how long coronavirus would interrupt our normal lives, we had to take things day by day. At the same time, we were risking burnout and and we needed a bigger business strategy.

Making Quality Events

Our Marketing Manager Marie and Executive Director Amanda came up with a virtual event format that would be fun and explore all the stories and places locals don’t know that is central to what we’ve always done as a tour company.  Saturday and Sunday afternoons were “neighborhood detours” that showed off unique architecture, cultural activities, and historic bars and restaurants of neighborhoods on the North, South and West sides.

For weekdays, our variety of topics included “Monday Conversations” with fellow interpreters of the city, like artists, historians, preservationists and journalists.  Tuesdays were for virtual road trips to destinations within driving distance of Chicago. Wednesdays were “People’s Histories” to highlight the lesser told stories of Chicago figures from the past. Fridays were about historic bars and old-school entertainment like theater.

My personal favorite was Thursdays: our Chicago Architecture Crash Course. Amanda and I planned, researched, and co-presented a 12-week long series of presentations on the different periods and styles of the city’s grand architectural traditions. It was honestly one of the most gratifying things I’ve ever done for Detours and it was thrilling to see a regular audience join us week after week.

virtual tours collage
This collage expresses just a few of the many topics we tackled on virtual tours. (Collage by Alex Bean)

Making Virtual Experiences Interactive

We weren’t the only tour or events company that jumped online during the onset of the pandemic. From the get-go, we stayed on top of what other museums, theaters, event planners and tour companies were creating for virtual experiences. We noticed that the experiences improved when they provided some level of interactivity. Plenty of tour companies were giving historic lectures, but just as in our tours, we wanted to engage and connect people.

We were also motivated by missing  the interactivity of  our walking tours. Our walking and bus tours had quick moments for fun and educational games. With our in-person tours, we have worked with thousands over the years for corporate team building experiences. We know that people love to be competitive, they love to learn, and they want to show off their creativity. So the team took our 10 years of designing games and considered how we could build those games in a virtual format. We started to brainstorm ways that we could make an experience interactive without fancy technology, but rather 100% human interaction brought to you via a Zoom event.

The whole team worked together in the design process to make a product that would appeal to corporate groups and conferences. We made a “Boat Tour Bingo” for the Cruise from Your Couch Virtual Boat Tours. We crafted a sheet of clues, each relating to sights and stories that we glimpse on that hour-long digital excursion. The game adds a layer of friendly competition to an already fun experience, with prizes for the winners to boot!

We also devised what we call “creative challenges.” For our Deep Slice of Chicago Food History, we explore how the various cultures of Chicago have shaped our unique cuisine. So we then have our corporate event clients collaborate in breakout rooms to create their own new signature dish that reflects our cultural history (and also tastes good!) We choose our favorites and then have the group vote for the winner!

Refining our Virtual Experiences

virtual boat tour river view
Images like this, from the Virtual Boat Tour, have given us a baseline to build from. Image courtesy of Google.

We then refined our virtual events, in terms of both quantity and presentation. It is an awful lot of work to create new content all the time! It was both a creatively stimulating process and an exhausting one. We narrowed down a few core virtual event products that we could make awesome and present regularly.

Our Virtual Boat Tour was an obvious inclusion as it was popular from the get-go. The boat tour virtual event got press coverage in Block Club Chicago, NBC, the Tribune, Fodor’s, Thrillist, and Time Out Chicago, We also selected virtual events dedicated to Chicago’s food and drink histories, the wonders of the 1893 World’s Fair, and the badass women of Chicago’s history. We’re constantly working to finesse the stories we tell and locate killer images for these virtual events. We’ve had video produced, too! We want our virtual  guests get an unmatched experience.

We now specialize in virtual events for private clients, like universities, families, and corporate teams. We have hosted conferences as well as the entire incoming class of the University of Chicago. I’ve personally hosted virtual tours for every one of those groups and it’s a richly rewarding experience. I love sharing the city’s stories with people who still cannot see it (and each other) for themselves.

The past few months’ of doing virtual events for more than 27,000 guests shows we have this whole virtual event thing down! We have taken our knowledge of architecture and history with our expertise in storytelling and team building for in-person tours and applied this to our virtual events. Like I said, I hope you can join us for the Virtual Holiday Stories Happy Hour this December!

– Alex Bean, Content Manager and Virtual Event Host


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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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