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See Chicago better than a local

Half and full-day tours

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2 to 200 guests

Expert tour guide

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Customized for your interests

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Private Custom
Downtown & Neighborhood Tours

Explore the city on the best Chicago private tour

Bring your corporate or social group on a Chicago private custom tour of dramatic landmarks, vibrant neighborhoods and fascinating backstories. Book a private tour with us!

Experience a Chicago private custom tour of dramatic landmarks, vibrant neighborhoods and fascinating backstories. Bring your group of friends, family or corporate colleagues to discover why our passionate tour guides made us “Best Tour of Chicago” runner-up two years in a row!  

We primarily work with corporate groups and educational institutions. Our tours host groups from 2 to 200 guests. 

REGULAR PRIVATE TOURS

Downtown Bucket List Tour

See it all on this half-driving, half-walking private tour! Your expert tour guide will share stories while you take in Chicago’s best downtown attractions. Your driving tour gives you a macro perspective, then you’ll get an inside and up-close look at the city on a walking tour in the Loop.

  • Experience a dramatic skyline view.

  • Ogle at Gold Coast historic mansions.

  • Step inside glitzy lobbies of art deco skyscrapers.

  • Learn about Chicago blues at a giant mural.

  • Grab a classic lunch at a historic restaurant.

  • Enter jaw-dropping landmarks like the Cultural Center, the Rookery and Medinah Athletic Club.

Chicago Neighborhoods Tour

Get to know Chicago’s character through the vibrant neighborhoods of the South, West and North Sides. Learn about their historic development, challenges and triumphs. You can support small businesses at brief stops, too. Book this private tour for a deeper perspective into Chicago.

  • Learn about how neighborhoods change.

  • Get a drink in a neighborhood dive bar.

  • Hear forgotten stories behind both famous and overlooked architecture.

  • Stop to buy artisan foods and gifts.

  • View innovative historic factory renovations.

  • Dine at a home-style Polish restaurant.

Downtown Bucket List Tour

See it all on this half-driving, half-walking private tour! Your expert tour guide will share stories while you take in Chicago’s best downtown attractions. Your driving tour gives you a macro perspective, then you’ll get an inside and up-close look at the city on a walking tour in the Loop.

  • Experience a dramatic skyline view.

  • Step inside skyscraper lobbies.

  • Learn about Chicago blues at a giant mural.

  • Grab lunch at a historic restaurant.

Chicago Neighborhoods Tour

Get to know Chicago’s character through the vibrant neighborhoods of the South, West and North Sides. Learn about their historic development, challenges and triumphs. You can support small businesses at brief stops, too. Book this private tour for a deeper perspective into Chicago.

  • Get a drink in a neighborhood dive bar.

  • Hear forgotten stories behind both famous and overlooked architecture.

  • View innovative historic factory renovations.

  • Dine at a home-style Polish restaurant.

Where do you want to go on your Chicago private custom tour?

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OUR TOURS HAVE BEEN FEATURED!

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CUSTOM PRIVATE TOUR PHOTOS

Meet your private Tour Guides

Alex Bean

"I love showing how we in the present can have a glimpse into the past by viewing buildings as physical remnants of history. Like if we are downtown, I'll show you the cowpath through a luxury hotel in the Loop! Also sharing historic locales of our Chicago foods, like the Maxwell Polish, is a treat to me."

Amanda Scotese

"One of my favorite parts of being a Chicago tour guide is making learning about architectural history fun and accessible for everyone. As your Chicago expert, I can take you into incredible architectural interiors and also gladly guide you to the best spots for a Chicago-style hot dog, donuts or hot chocolate.

Marie Rowley

"I love introducing newcomers to Chicago highlights and revealing neighborhood secrets to local Chicagoans. Let's grab something to sip from a rooftop bar of a historic skyscraper! As your Chicago tour guide, I'll share stories of the diverse people who deserve bigger entries in the Chicago history books."

Alex Bean

"I love showing how we in the present can have a glimpse into the past by viewing buildings as physical remnants of history.

Amanda Scotese

"As your Chicago expert, I can take you into incredible architectural interiors and also gladly guide you to the best spots for a Chicago-style hot dog.

Marie Rowley

"As your Chicago tour guide, I'll share stories of the diverse people who deserve bigger entries in the Chicago history books."

why our CUSTOM tours are the best

Our team of expert tour guides know how to curate a killer Chicago private custom tour experience. We’ve been top-rated since 2010 on TripAdvisor and Yelp, and we have hosted more than 125,000 virtual and in-person tour guests.

We love to bring curious people to explore stories and places even locals don’t know of Chicago history, architecture and culture, and hope you’ll choose us as your Chicago expert!

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Can’t say enough about this tour - an absolute blast.
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robcalice TripAdvisor
We have so many great memories from the tour and we learned a lot.
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Nicole Yelp
Best tour of Chicago
"BEST TOUR" RUNNER-UP 2020

Looking for a Larger Tour?

We accommodate large groups of 50 to 500+ on
custom walking and bus tours in downtown Chicago or in our neighborhoods.
Let's talk

Got a Large Group?

Contact us for groups of 50 to 500+.
Let's talk

PRIVATE TOUR RATES

Phone

Private group tour rates start at a $425 flat rate.
Call us: 312.350.1131
Email us: [email protected]

Book a private tour!

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SEE THE BEST OF CHICAGO

 


Ellen

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.”
Robert
GetYourGuide

Jen

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.”
Heather
TripAdvisor

Elyse

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.

Anthony

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.

Marie

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.”
Lorit
TripAdvisor

Sonny

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
TripAdvisor

Alex

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
Yelp

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
Yelp

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