A Chicago Tour Company

Our Story a.k.a. the History of Us!

Chicago Detours is a boutique experiential travel company that was one of the first in the world to foresee the trend toward local-based, authentic travel experiences. 


The Chicago Detours began
1 st
hyperlocal tourism company in the country!
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in-person and virtual tour guests
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reviews with average rating of 4.5/5
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Custom-designed walking, bus and boat tours in downtown and Chicago neighborhoods
Curated virtual events with 300+ hours development
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donated to a youth theater program that shares stories of our neighborhoods
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blog posts about Chicago history, architectural design and things to do

our journey as a Chicago tour company


Founder Amanda Scotese created Detours as a Chicago tour company with a mission to bring people to explore Chicago stories and places that even locals didn’t know.

Before Chicago Detours, she worked in travel for many years, including a decade as a Tour Guide and Guidebook Researcher with Rick Steves’ Europe.

We designed walking, bus and boat tours of downtown and Chicago neighborhoods.

Amanda and the Chicago Detours team cultivated a reputation as having the best Chicago tour guides, with five stars on Google, Facebook, TripAdvisor and Yelp. 

We supported education in history and architecture with our Community Initiatives

chicago expert neighborhood tour guide alex speaking chicago tour company

Voted Runner-up for “Best Tour of Chicago” in the Chicago Reader’s annual poll.

Best tour of Chicago

We celebrated our 10th anniversary as a Chicago tour company! 

We used our background in visual storytelling, our expertise in Chicago architecture and history, and a decade of curating corporate events to launch virtual tours.

These were featured in Entrepreneur, Inc. Magazine, WBEZ and many more. 


We officially launched our place-based storytelling and content production services, including video, animations, and all kinds of media for telling Chicago stories.

chicago neighborhood video production amanda with camera on shoot
2022 year

Expanded into experiential consulting projects for visitor experiences. Clients include Driehaus Museum, American Writers Museum and Design Museum of Chicago. 

“Chicago Detours, a touring company…pushing the limits of what is expected.”

Entrepreneur Magazine 3/18/21

Actually Cool Things You Can (Still) Do in Chicago Right Now

thrillist 8/15/2020

How 5 Small Businesses Reinvented Themselves During Covid 

Inc Magazine 3/17/21

meet the team

Executive Director and Tour Guide

Content Manager and Tour Guide

Marketing Manager and Tour Guide

Sales Manager and Tour Guide

Tour Guide

chai headshot tour company assistant

Administrative Assistant

Our Chicago Tour Company Philosophy

We believe we can learn about our communities, ourselves and each other by exploring Chicago history and architecture.

We know that history is best told with a creative approach.

custom chicago neighborhoods building tour icon

We passionately support historic preservation efforts.

river city chicago architecture stories event

ready to book a tour?


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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