Decade in Review as a Small Business in Chicago

We are gearing up to celebrate 10 years as a small business here in the fine city of Chicago. The end of the 2010s marks the end of our first decade! Amanda Scotese, our fearless small business leader, founded Chicago Detours back in 2010. In that time we have grown by leaps and bounds. We are finishing the decade on a high note, placing second in the Reader’s “Best Tour in Chicago” poll. We’re incredibly proud of the tours we lead, the work we do, and the team we’ve assembled. Here are some highlights from the first (but not last) decade in Chicago Detours’ history.

Before the Birth of a Chicago Small Business

Rick Steves Chicago Detours
Rick was our tour guest on our Loop Interior Architecture Tour back in 2016.

Before Chicago Detours, Amanda worked for Rick Steves’ Europe. She was a tour guide and book editor in Italy for a decade. In that time, she got firsthand feedback on what we want out of the best possible tour experience:

  1. We want to learn
  2. We want to have fun
  3. We want to connect with the places we visit

These three points would in time become the lodestar of Chicago Detours. Before that could happen though, Amanda has to be in Chicago and not Italy.  With the goal of starting a tour business, she started studying architectural history and anything focused on Chicago for her Master’s degree at the University of Chicago. Chicago Detours grew from her studies there.

Early Chicago Tours

Amanda Chicago Detours small business in chicago
Amanda guiding one of the early iterations of the Historic Chicago Walking Bar Tour.

The first questions that confront the creation of a new tour company must have been plenty. What are you going to show people? Will they be walking tours or bus tours? When will you offer these events? How will you be different from other tour companies? How do you get people to book a tour? Personally, I quake at the idea of confronting such issues for a new small business in Chicago.

Amanda leaned in by finding new angles on some very popular areas. She started with the Mag Mile, delving through archival material to concoct a “Detour” in the most tourist-friendly neighborhood in the city. Guests on the “Good Times on the Mag Mile” tour mentioned that it would be fun to grab drinks along the way. Thus, this walking tour eventually evolved into the Historic Chicago Walking Bar Tour.

Then winter hit! Amanda decided to go inside and underground in the Loop. This new tour slowed down while exploring glorious indoor spaces like the Chicago Temple, the Cultural Center, and the Pedway. Thus was born our best-selling tour of the decade, the Loop Interior Architecture Walking Tour.

Groupon featured these early Detours on Christmas Day, December 2010. Odd as it sounds today, a featured deal on Groupon actually meant something in late 2010. Today, we still have tour regulars who originally heard of Chicago Detours through that deal. These early winds of success helped Detours kick the decade (and its existence) off with aplomb.

Steady Growth of a Small Business in Chicago

Jazz Blues Beyond Tour Chicago Detours
Guests on the Jazz, Blues, and Beyond Tour inspect murals inside the former Sunset Cafe.

These early successes led us to put the show on the road for our small business in Chicago. Amanda designed our first bus tour, the Jazz, Blues, and Beyond tour, in 2011. The experience, which can be booked as a private group tour, visits famous venues like the Green Mill, along with half-forgotten spots, like the former Sunset Cafe. Later bus tours for private groups, like the Chicago Neighborhoods and Cultural Diversity Tour, would be built upon this blueprint.

Corporate groups, families, and friends celebrating birthdays started booking these walking and bus tours, and Amanda couldn’t do it alone. With a vision of making something bigger, she brought on employees in 2011. She turned over responsibilities like managing the public tours and coordinating private group tours.

We noticed that tour guests on the Loop Interior Architecture Walking Tour kept asking if there was a map of the Pedway. Amanda designed a user-friendly map to help people explore the Pedway. We released our Pedway map in 2012 (and are releasing an update in a few weeks). 2012 is the same year that our longest-tenured employee, Lead Tour Guide Elizabeth, joined our crew.

Half-Way Through the Small Business Journey

In the middle of our decade, Chicago Detours took off as a small business in Chicago. We celebrated our fifth anniversary in 2015 with a giant celebration. The party included a preview of the new Big Shoulders Historic Bar and Food Tour in Bridgeport, and then a reception at a Gilded Age mansion in Bronzeville (the Welcome Inn Manor B&B).

Chicago Detours team member Pawel Skrabacz, helped make it happen. He joined the crew as Private Tour Coordinator in 2014, eventually leaving on his “Culture Ride” to Patagonia in 2017. Yours truly also came aboard at this time, joining the Detours staff in late 2015, right as we started to expand our tour offerings. A lot of our locals had already done the two walking tours we offered, and they wanted more!

So, in the 18 months after I started, we designed the 1893 World’s Fair Tour, the Wicker Park and Old Polonia Food Tour, and the Holiday Tour of Drinks, Daleys, and Dead Guys. We also began to work with large-scale clients, working as tour provider for a major conference and creating monthly experiences for the University of Chicago Alumni Association.

We hosted our first Badass Women of Chicago History storytelling event to expand our content beyond tours in 2018. That same year we started regularly offering the Factories to Calories Fulton Market Food Tour.

Our small business has grown to be the largest small tour company in Chicago! The next step up from us are huge non-profit organizations, with volunteer guides, or the giant boat tour companies. Don’t get us wrong, though, we can go big. Groups of up to 400 guests at one time, in fact. Plus, we provide the coolest tour experience possible while we’re at it!

Here’s to Another 10 Years as a Small Business

Chicago Detours tour guides
The Detours team circa 2019.

2020 marks great anniversaries for our office staff, who all double as tour guides. Operations Manager Sonny Turski will celebrate four years with us. Marketing Manager Marie Rowley will celebrate three years and Private Tour Coordinator Ellen Bushong will be at two years. Jennifer Wilson-Fojo, our Private Tour Coordinator, will be at one year next month!

Speaking of 2020, we have a lot of fun stuff planned for our tenth anniversary. We’ll keep offering the tours of Chicago’s interior architecture, historic bars, and music history, of course. You can also look forward to the regularly scheduled Architecture of Money and Power Financial District Tour and Century of Contrasts South Loop Tour. Plus, we have a whole bevy of special events in Chicago as a thanks to those who have supported our small business over the years!

See you then!

– Alex Bean, Content Manager and Tour Guide


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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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