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See Chicago better than a local

Half- or full-day private tour

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11 or fewer guests

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Customized for food, photos, your interests

Fun modes of transport

Neighborhoods Tour

for a custom experience

Explore Chicago on a fun and flexible custom private neighborhood tour. Choose to stay downtown or visit Chicago neighborhoods – or both! Families, friends, or company outings with 11 or fewer guests will see Chicago on an experience customized to their interests.

Let us be your Chicago neighborhood expert on history, architecture, food, drinks and things to do. Our passionate expert tour guides have gotten us voted for the last two years as “Best Tour of Chicago.”

We can customize your neighborhood tour to be partly by  walking, a ride share, the CTA or biking. We can also book a chauffeured Tesla sedan and have additional options for larger groups. 

Visit our diverse neighborhoods and you’ll support small businesses when you book this one-of-a-kind private tour.  We can customize it for you when you book or we can do it “off-the-cuff” when you meet your tour guide. 

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  • Nibble on apps at a hip or historic restaurant.
  • Learn about famous and overlooked architecture.
  • Get a drink in a neighborhood dive bar.
  • Step into glitzy lobbies in the Financial District.
  • Snap iconic photos of the skyline or street art.
  • Take a coffee break and people watch on the Riverwalk.
  • Ride the ‘L’ train loop and gaze at skyscrapers.
  • Stop to buy artisan foods and gifts.
  • Stroll from Wicker Park to Logan Square on the “606.” 
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Meet your private tour guides

Alex Bean

"I love showing how buildings are physical remnants of history that let us in the present have a glimpse into the past. Sharing the historic locales of our Chicago foods, like the Maxwell Polish, is a treat to me. I live near the lakefront in Lincoln Park."

Amanda Scotese

"I am fascinated with how and why Chicago neighborhoods change, and I love getting people to understand the built world around them. I'll take you to the best spots for pastries or hot chocolate. I live on the Northwest Side in the Avondale neighborhood.

Marie Rowley

"I love sharing stories of all the diverse people from Chicago history who really should be in our history books. As your tour guide, I'll take you out for Polish pierogi or Filipino adobo, and I can show you Ravenswood and Lincoln Square like nobody else."


Our expert tour guides know how to curate a killer experience. We’ve been a top-rated tour company since 2010 on TripAdvisor and Yelp.

We have hosted more than 75,000 private tour guests. We love to bring curious people to explore stories and places even locals don’t know of history and architecture in Chicago neighborhoods. 

So much yummy food and a grand way to spend time with friends!
A whole new way of looking at the city!

curious about a private tour?



Call us to discuss your custom private tour! We want to know your group's neighborhood bucket lists, their preferred modes of transport, and interests for sites, food and photo ops.


We also have custom tour options for larger corporate events.








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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